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  • 151. Wang, Xin
    et al.
    Matei, Elena
    Deng, Lingquan
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Gronenborn, Angela M.
    Yan, Mingdi
    KTH, Skolan för kemivetenskap (CHE), Kemi.
    Multivalent glyconanoparticles with enhanced affinity to the anti-viral lectin Cyanovirin-N2011Inngår i: Chemical Communications, ISSN 1359-7345, E-ISSN 1364-548X, Vol. 47, nr 30, s. 8620-8622Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    Low-mannose (LM) structures were coupled to gold nanoparticles (Au NPs) to amplify the affinity of LMs with Cyanovirin-N (CV-N) lectins and to study the structures of CV-N variants CVN(Q50C) and CVN(MutDB).

  • 152. Wang, Xin
    et al.
    Matei, Elena
    Gronenborn, Angela M.
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Yan, Mingdi
    KTH, Skolan för kemivetenskap (CHE), Kemi.
    Direct Measurement of Glyconanoparticles and Lectin Interactions by Isothermal Titration Calorimetry2012Inngår i: Analytical Chemistry, ISSN 0003-2700, E-ISSN 1520-6882, Vol. 84, nr 10, s. 4248-4252Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    Glyconanomaterials have shown high potential in applications including bioanalysis and nanomedicine. Here, a quantitative analytical technique, based on isothermal titration calorimetry, was developed to characterize the interactions between glyconanoparticles and lectins. By titrating lectins into the glyconanoparticle solution, the apparent dissociation constant, thermodynamic parameters, and the number of binding sites were derived simultaneously. For the glyconanoparticles-lectin binding pairs investigated, a 3-5 order of magnitude affinity enhancement over the free ligand-lectin interactions was observed which can be attributed to the multivalent ligand presentation on the nanoparticles. The impact of ligand density was also studied, and results showed that the affinity increased with the number of glycans on the nanoparticle.

  • 153.
    Wang, Xin
    et al.
    Portland State University, United States .
    Norberg, Oscar
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Deng, Lingquan
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Yan, Mingdi
    KTH, Skolan för kemivetenskap (CHE), Kemi. Portland State University, United States .
    Synthesis of Glyconanomaterials via Photo-Initiated Coupling Chemistry2011Inngår i: Petite and sweet: glyco-nanotechnology as a bridge to new medicines, American Chemical Society (ACS), 2011, Vol. 1091, s. 49-67Konferansepaper (Fagfellevurdert)
    Abstract [en]

    Glyconanomaterials, broadly defined as carbohydrate-presenting structures below 100 nm in size, exhibit remarkable chemical and physical properties with high potential for modern biomedical applications. In this chapter, current synthetic approaches for fabricating glyconanomaterials are summarized, with special emphasis on a novel photocoupling strategy to conjugate carbohydrates onto a wide variety of nanomaterials. Based on the photochemically induced reaction of perfluorophenylazide, different glyconanomaterials were efficiently synthesized, and the resulting structures used in a range of applications. The results demonstrate that this approach to carbohydrate presentation at nanomaterial surfaces leads to efficient and selective binding to cognate proteins, enabling new applications in carbohydrate-lectin recognition, profiling, biosensing, screening, cell imaging, and bacteria detection.

  • 154. Wang, Xin
    et al.
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Yan, Mingdi
    KTH, Skolan för kemivetenskap (CHE), Kemi.
    A photochemically initiated chemistry for coupling underivatized carbohydrates to gold nanoparticles2009Inngår i: Journal of Materials Chemistry, ISSN 0959-9428, E-ISSN 1364-5501, Vol. 19, nr 47, s. 8944-8949Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    The sensitive optoelectronic properties of metal nanoparticles make nanoparticle-based materials a powerful tool to study fundamental biorecognition processes. Here we present a new and versatile method for coupling underivatized carbohydrates to gold nanoparticles (Au NPs) via the photochemically induced reaction of perfluorophenylazide (PFPA). A one-pot procedure was developed where Au NPs were synthesized and functionalized with PFPA by a ligand-exchange reaction. Carbohydrates were subsequently immobilized on the NPs by a fast light activation. The coupling reaction was efficient, resulting in high coupling yield as well as high ligand surface coverage. A colorimetric system based on the carbohydrate-modified Au NPs was used for the sensitive detection of carbohydrate-protein interactions. Binding and cross-reactivity studies were carried out between carbohydrate-functionalized Au NPs and lectins. Results showed that the surface-bound carbohydrates not only retained their binding affinities towards the corresponding lectin, but also exhibited affinity ranking consistent with that of the free ligands in solution.

  • 155. Wang, Xin
    et al.
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Yan, Mingdi
    KTH, Skolan för kemivetenskap (CHE), Kemi.
    Dye-doped silica nanoparticles as efficient labels for glycans2011Inngår i: Chemical Communications, ISSN 1359-7345, E-ISSN 1364-548X, Vol. 47, nr 14, s. 4261-4263Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    We report that dye-doped fluorescent silica nanoparticles (FSNPs) are highly efficient labels for glycans. Mono- and oligo-saccharides were conjugated to FSNPs using a general photocoupling chemistry. FSNP-labeled glycans were applied to image and detect bacteria, and to study carbohydrate-lectin interactions on a lectin microarray.

  • 156. Wang, Xin
    et al.
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi.
    Yan, Mingdi
    KTH, Skolan för kemivetenskap (CHE), Kemi.
    Dynamic light scattering as an efficient tool to study glyconanoparticle-lectin interactions2011Inngår i: The Analyst, ISSN 0003-2654, E-ISSN 1364-5528, Vol. 136, nr 20, s. 4174-4178Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    Glyconanomaterials, an emerging class of bio-functional nanomaterials, have shown promise in detecting, imaging and targeting proteins, bacteria, and cells. In this article, we report that dynamic light scattering (DLS) can be used as an efficient tool to study glyconanoparticle (GNP)-lectin interactions. Silica and Au nanoparticles (NPs) conjugated with D-mannose (Man) and D-galactose (Gal) were treated with the lectins Concanavalin A (Con A) and Ricinus communis agglutinin (RCA(120)), and the hydrodynamic volumes of the resulting aggregates were measured by DLS. The results showed that the particle size grew with increasing lectin concentration. The limit of detection (LOD) was determined to be 2.9 nM for Con A with Man-conjugated and 6.6 nM for RCA(120) with Gal-conjugated silica NPs (35 nm), respectively. The binding affinity was also determined by DLS and the results showed 3-4 orders of magnitude higher affinity of GNPs than the free ligands with lectins. The assay sensitivity and affinity were particle size dependent and decreased with increasing particle diameter. Because the method relies on the particle size growth, it is therefore general and can be applied to nanomaterials of different compositions.

  • 157. Wang, Xin
    et al.
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Yan, Mingdi
    KTH, Skolan för kemivetenskap (CHE), Kemi.
    Glyconanomaterials: Synthesis, Characterization, and Ligand Presentation2010Inngår i: Advanced Materials, ISSN 0935-9648, E-ISSN 1521-4095, Vol. 22, nr 17, s. 1946-1953Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    Glyconanomaterials, nanomaterials carrying surface-tethered carbohydrate ligands, have emerged and demonstrated increasing potential in biomedical imaging, therapeutics, and diagnostics. These materials combine the unique properties of nanometer-scale objects with the ability to present multiple copies of carbohydrate ligands, greatly enhancing the weak affinity of individual ligands to their binding partners. Critical to the performance of glyconanomaterials is the proper display of carbohydrate ligands, taking into consideration of the coupling chemistry, the type and length of the spacer linkage, and the ligand density. This article provides an overview of the coupling chemistry for attaching carbohydrate ligands to nanomaterials, and discusses the need for thorough characterization of glyconanomaterials, especially quantitative analyses of the ligand density and binding affinities. Using glyconanoparticles synthesized by a versatile photocoupling chemistry, methods for determining the ligand density by colorimetry and the binding affinity with lectins by a fluorescence competition assay are determined. The results show that the multivalent presentation of carbohydrate ligands significantly enhances the binding affinity by several orders of magnitude in comparison to the free ligands in solution. The effect is sizeable even at low surface ligand density. The type and length of the spacer linkage also affect the binding affinity, with the longer linkage promoting the association of bound ligands with the corresponding lectins.

  • 158. Wang, Xin
    et al.
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Yan, Mingdi
    KTH, Skolan för kemivetenskap (CHE), Kemi.
    Quantitative Analysis of Multivalent Ligand Presentation on Gold Glyconanoparticles and the Impact on Lectin Binding2010Inngår i: Analytical Chemistry, ISSN 0003-2700, E-ISSN 1520-6882, Vol. 82, nr 21, s. 9082-9089Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    Glyconanomaterials, nanomaterials carrying multiple carbohydrate ligands, provide an excellent platform for sensitive protein recognition. Using nanomaterials as the scaffold, multivalent interactions between glycan ligands and proteins have been demonstrated. However, the quantitative analysis of the binding affinity of these glyconanomaterials has been lacking. In this Article, we report a new method to measure the binding affinity of glyconanoparticle (GNP)-protein interactions based on a fluorescent competition binding assay, which yielded the apparent dissociation constant (K-d) of GNPs with the interacting protein. Au nanoparticles conjugated with underivatized mono-, oligo-, and polysaccharides were synthesized using our recently developed photocoupling chemistry. The affinities of these GNPs with lectins were measured and were several orders of magnitude higher than the corresponding free ligands with lectins. The effect of ligand display on the binding affinity of GNPs was, furthermore, studied where GNPs of varying linker type, spacer length, ligand density, and nanoparticle size were prepared and K-d values determined. The long spacer linker containing hydrocarbon and ethylene oxide units gave the highest binding affinity as well as assay sensitivity. The binding affinity increased with ligand density in general, showing a drastic increase in affinity at low ligand density. In addition, the affinity enhancement was more pronounced on smaller NPs than the larger ones. These results not only demonstrate that the binding affinity of GNPs is highly influenced by how the ligands are presented on the nanoparticles but also pave the way for tailor-made glyconanomaterials with tunable affinity by way of ligand display.

  • 159.
    Xie, Sheng
    et al.
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Fukumoto, Ryo
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Yan, Mingdi
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi. University of Massachusetts, United States.
    Anilide Formation from Thioacids and Perfluoroaryl Azides2015Inngår i: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 80, nr 9, s. 4392-4397Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    A metal-free method for fast and clean anilide formation from perfluoroaryl azide and thioacid is presented. The reaction proved highly efficient, displaying fast kinetics, high yield, and good chemoselectivity. The transformation was compatible with various solvents and tolerant to a wide variety of functional groups, and it showed high performance in polar protic/aprotic media, including aqueous buffer systems.

  • 160.
    Xie, Sheng
    et al.
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi. Univ Massachusetts Lowell, Dept Chem, Lowell, MA 01854 USA.
    Lopez, Steven A.
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Yan, Mingdi
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi. Department of Chemistry, University of Massachusetts Lowell, Lowell, MA, United States .
    Houk, K. N.
    1,3-Dipolar Cycloaddition Reactivities of Perfluorinated Aryl Azides with Enamines and Strained Dipolarophiles2015Inngår i: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 137, nr 8, s. 2958-2966Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    The reactivities of enamines and predistorted (strained) dipolarophiles toward perfluoroaryl azides (PFAAs) were explored experimentally and computationally. Kinetic analyses indicate that PFAAs undergo (3 + 2) cycloadditions with enamines up to 4 orders of magnitude faster than phenyl azide reacts with these dipolarophiles. DFT calculations were used to identify the origin of this rate acceleration. Orbital interactions between the cycloaddends are larger due to the relatively low-lying LUMO of PFAAs. The triazolines resulting from PFAAenamine cycloadditions rearrange to amidines at room temperature, while (3 + 2) cycloadditions of enamines and phenyl azide yield stable, isolable triazolines. The 1,3-dipolar cycloadditions of norbornene and DIBAC also show increased reactivity toward PFAAs over phenyl azide but are slower than enamineazide cycloadditions.

  • 161.
    Xie, Sheng
    et al.
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Manuguri, Sesha
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Hao, Nanjing
    Zhang, Yang
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Zhou, Juan
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Yan, Mingdi
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi. University of Massachusetts, United States .
    Design and synthesis oftheranostic antibiotic nanodrugs that display size-dependent antibacterial activity and luminescenceManuskript (preprint) (Annet vitenskapelig)
  • 162.
    Xie, Sheng
    et al.
    KTH, Skolan för kemivetenskap (CHE), Kemi.
    Manuguri, Sesha
    KTH, Skolan för kemivetenskap (CHE), Kemi.
    Proietti, Giampiero
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Romson, Joakim
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Fu, Ying
    KTH, Skolan för teknikvetenskap (SCI), Tillämpad fysik, Cellulär biofysik. KTH, Centra, Science for Life Laboratory, SciLifeLab.
    Inge, A. K.
    Wu, B.
    Zhang, Yang
    KTH, Skolan för kemivetenskap (CHE), Kemi.
    Häll, Daniel
    KTH, Skolan för kemivetenskap (CHE), Kemi.
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi.
    Yan, Mingdi
    KTH, Skolan för kemivetenskap (CHE), Kemi.
    Design and synthesis of theranostic antibiotic nanodrugs that display enhanced antibacterial activity and luminescence2017Inngår i: Proceedings of the National Academy of Sciences of the United States of America, ISSN 0027-8424, E-ISSN 1091-6490, Vol. 114, nr 32, s. 8464-8469Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    We report the modular formulation of ciprofloxacin-based pure theranostic nanodrugs that display enhanced antibacterial activities, as well as aggregation-induced emission (AIE) enhancement that was successfully used to image bacteria. The drug derivatives, consisting of ciprofloxacin, a perfluoroaryl ring, and a phenyl ring linked by an amidine bond, were efficiently synthesized by a straightforward protocol from a perfluoroaryl azide, ciprofloxacin, and an aldehyde in acetone at room temperature. These compounds are propeller-shaped, and upon precipitation into water, readily assembled into stable nanoaggregates that transformed ciprofloxacin derivatives into AIE-active luminogens. The nanoaggregates displayed increased luminescence and were successfully used to image bacteria. In addition, these nanodrugs showed enhanced antibacterial activities, lowering the minimum inhibitory concentration (MIC) by more than one order of magnitude against both sensitive and resistant Escherichia coli. The study represents a strategy in the design and development of pure theranostic nanodrugs for combating drug-resistant bacterial infections.

  • 163.
    Xie, Sheng
    et al.
    KTH, Skolan för kemi, bioteknologi och hälsa (CBH), Kemi, Organisk kemi. College of Chemistry and Chemical Engineering, Hunan University, Changsha, 410082, China.
    Manuguri, Sesha
    KTH, Skolan för kemi, bioteknologi och hälsa (CBH), Kemi.
    Ramström, Olof
    KTH, Skolan för kemi, bioteknologi och hälsa (CBH), Kemi, Organisk kemi. University of Massachusetts Lowell, 1 University Ave., Lowell, MA 01854, United States.
    Yan, Mingdi
    KTH, Skolan för kemi, bioteknologi och hälsa (CBH), Kemi, Organisk kemi. University of Massachusetts Lowell, 1 University Ave., Lowell, MA 01854, United States.
    Impact of Hydrogen Bonding on the Fluorescence of N-Amidinated Fluoroquinolone2019Inngår i: Chemistry - An Asian Journal, ISSN 1861-4728, E-ISSN 1861-471X, Vol. 14, nr 6, s. 910-916Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    The fluorescence properties of AIE-active N-amidinated fluoroquinolones, efficiently obtained by a perfluoroaryl azide-aldehyde-amine reaction, have been studied. The fluorophores were discovered to elicit a highly sensitive fluorescence quenching response towards guest molecules with hydrogen-bond-donating ability. This effect was evaluated in a range of protic/aprotic solvents with different H-bonding capabilities, and also in aqueous media. The influence of acid/base was furthermore addressed. The hydrogen-bonding interactions were studied by IR, NMR, UV/Vis and time-resolved fluorescence decay, revealing their roles in quenching of the fluorescence emission. Due to the pronounced quenching property of water, the N-amidinated fluoroquinolones could be utilized as fluorescent probes for quantifying trace amount of water in organic solvents.

  • 164.
    Xie, Sheng
    et al.
    KTH, Skolan för kemi, bioteknologi och hälsa (CBH), Kemi, Organisk kemi.
    Proietti, Giampiero
    KTH, Skolan för kemi, bioteknologi och hälsa (CBH), Kemi, Organisk kemi.
    Ramström, Olof
    KTH, Skolan för kemi, bioteknologi och hälsa (CBH), Kemi, Organisk kemi.
    Yan, Mingdi
    Univ Massachusetts Lowell, Dept Chem, Lowell, MA 01854 USA..
    Photoactivatable Fluorogens by Intramolecular C-H Insertion of Perfluoroaryl Azide2019Inngår i: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 84, nr 22, s. 14520-14528Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    Molecules, capable of fluorescence turn-on by light, are highly sought-after in spatio-temporal labeling, surface patterning, monitoring cellular and molecular events, and high-resolution fluorescence imaging. In this work, we report a fluorescence turn-on system based on photoinitiated intramolecular C-H insertion of azide into the neighboring aromatic ring. The azide-masked fluorogens were efficiently synthesized via a cascade nucleophilic aromatic substitution of perfluoroaryl azides with carbazoles. The scaffold also allows for derivatization with biological ligands, as exemplified with D-mannose in this study. This photoinitiated intramolecular transformation led to high yields, high photo-conversion efficiency, and well-separated wavelengths for photoactivation and fluorescence excitation. The mannose-derivatized structure enabled spatio-temporal activation and showed high contrast and signal amplification. Live cell imaging suggested that the mannose-tagged fluorogen was transported to the lysosomes.

  • 165.
    Xie, Sheng
    et al.
    KTH, Skolan för kemivetenskap (CHE), Kemi.
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Yan, Mingdi
    KTH, Skolan för kemivetenskap (CHE), Kemi. University of Massachusetts Lowell, United States.
    N,N-Diethylurea-Catalyzed Amidation between Electron-Deficient Aryl Azides and Phenylacetaldehydes2015Inngår i: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 17, nr 3, s. 636-639Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    Urea structures, of which N,N-diethylurea (DEU) proved to be the most efficient, were discovered to catalyze amidation reactions between electron-deficient aryl azides and phenylacetaldehydes. Experimental data support 1,3-dipolar cycloaddition between DEU-activated enols and electrophilic phenyl azides, especially perfluoroaryl azides, followed by rearrangement of the triazoline intermediate. The activation of the aldehyde under near-neutral conditions was of special importance in inhibiting dehydration/aromatization of the triazoline intermediate, thus promoting the rearrangement to form aryl amides.

  • 166.
    Xie, Sheng
    et al.
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Yan, Mingdi
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi. University of Massachusetts, United States .
    Photo-activatable switch-on fluorescence through intramolecular C-H insertion of azide derivativesManuskript (preprint) (Annet vitenskapelig)
  • 167.
    Xie, Sheng
    et al.
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Zhang, Yang
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Yan, Mingdi
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi. University of Massachusetts, United States .
    Base-catalysed synthesis of aryl amides from aryl azides and aldehydesManuskript (preprint) (Annet vitenskapelig)
  • 168.
    Xie, Sheng
    et al.
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Zhang, Yang
    KTH, Skolan för kemivetenskap (CHE), Kemi.
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Yan, Mingdi
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Base-catalyzed synthesis of aryl amides from aryl azides and aldehydes2016Inngår i: Chemical Science, ISSN 2041-6520, E-ISSN 2041-6539, Vol. 7, nr 1, s. 713-718Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    Aryl amides have been used as important compounds in pharmaceuticals, materials and in molecular catalysis. The methods reported to prepare aryl amides generally require very specific reagents, and the most popular carboxyl-amine coupling reactions demand stoichiometric activators. Herein, we report that aryl azides react with aldehydes under base-catalyzed conditions to yield aryl amides efficiently. Mechanistic investigations support the formation of triazoline intermediates via azide-enolate cycloaddition, which subsequently undergo rearrangement to give amides by either thermal decomposition (20-140 degrees C) or aqueous acid work-up at room temperature. The strategy does not require nucleophilic anilines and is especially efficient for highly electron-deficient aryl amides, including perfluoroaryl amides, which are otherwise challenging to synthesize.

  • 169.
    Xie, Sheng
    et al.
    KTH, Skolan för kemi, bioteknologi och hälsa (CBH), Kemi, Organisk kemi.
    Zhou, Juan
    Chen, Xuan
    Univ Massachusetts Lowell, Dept Chem, Lowell, MA 01854 USA..
    Kong, Na
    Fan, Yanmiao
    KTH, Skolan för kemi, bioteknologi och hälsa (CBH), Kemi, Organisk kemi.
    Hammer, Gerry
    Univ Washington, Dept Bioengn, Natl ESCA & Surface Anal Ctr Biomed Problems, Seattle, WA 98195 USA.;Univ Washington, Dept Chem Engn, Natl ESCA & Surface Anal Ctr Biomed Problems, Seattle, WA 98195 USA..
    Castner, David G.
    Univ Washington, Dept Bioengn, Natl ESCA & Surface Anal Ctr Biomed Problems, Seattle, WA 98195 USA.;Univ Washington, Dept Chem Engn, Natl ESCA & Surface Anal Ctr Biomed Problems, Seattle, WA 98195 USA..
    Ramström, Olof
    KTH, Skolan för kemi, bioteknologi och hälsa (CBH), Kemi, Organisk kemi.
    Yan, Mingdi
    KTH, Skolan för kemi, bioteknologi och hälsa (CBH), Kemi, Organisk kemi.
    A versatile catalyst-free perfluoroaryl azide-aldehyde-amine conjugation reaction2019Inngår i: MATERIALS CHEMISTRY FRONTIERS, ISSN 2052-1537, Vol. 3, nr 2, s. 251-256Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    In a tri-component reaction, an electrophilically-activated perfluoroaryl azide, an enolizable aldehyde and an amine react readily at room temperature without any catalysts in solvents including aqueous conditions to yield a stable amidine conjugate. The versatility of this reaction is demonstrated in the conjugation of an amino acid without prior protection of the carboxyl group, and in the synthesis of antibiotic-nanoparticle conjugates.

  • 170.
    Yan, Mingdi
    et al.
    KTH, Skolan för kemivetenskap (CHE), Kemi.
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Moleculary Imprinted Materials: Science and Technology2005Bok (Fagfellevurdert)
  • 171.
    Yan, Mingdi
    et al.
    KTH, Skolan för kemivetenskap (CHE), Kemi.
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Preface2005Inngår i: Molecularly Imprinted Materials: Science and Technology, New York: Taylor & Francis , 2005Kapittel i bok, del av antologi (Annet vitenskapelig)
  • 172.
    Yan, Mingdi
    et al.
    KTH, Skolan för kemivetenskap (CHE), Kemi.
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi.
    Liu, Li-Hong
    Method for functionalizing materials and devices comprising such materials2007Patent (Annet (populærvitenskap, debatt, mm))
    Abstract [en]

    Devices comprising functionalized materials, and embodiments of a method for making and using such devices, are disclosed. Exemplary devices include ophthalmic devices, nanoparticles, quartz crystal microbalances, microarrays, and nanocomposites. In particular embodiments, device surfaces are modified with monomers and/or polymers, typically carbohydrate monomers and/or polymers. Embodiments of a method for making and using such devices are disclosed. Monomers and/or polymers are covalently bonded to surfaces using functionalized perhalophenylazides. In some embodiments, devices surfaces are functionalized with a perhalophenylazide. One or more monomers and/or polymers subsequently are covalently bonded to the device surface using the perhalophenylazide. In other embodiments, monomers and/or polymers are derivatized with a functionalized perhalophenylazide.; The derivatized monomers and/or polymers then are covalently bonded to the device surface using the perhalophenylazide.

  • 173. Yilmaz, E.
    et al.
    Ramström, Olof
    KTH, Tidigare Institutioner                               , Kemi.
    Moller, P.
    Sanchez, D.
    Mosbach, K.
    A facile method for preparing molecularly imprinted polymer spheres using spherical silica templates2002Inngår i: Journal of Materials Chemistry, ISSN 0959-9428, E-ISSN 1364-5501, Vol. 12, nr 5, s. 1577-1581Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    A novel and facile preparation method for spherical molecularly imprinted polymer (MIP) beads is presented. Two types of beads were synthesized and investigated: (i) silica-MIP composites were obtained by filling spherical, porous C-4-coated silica beads with print molecule and monomers followed by polymerisation; (ii) spherical molecularly imprinted polymer beads were acquired mirroring the silica particles in size, shape and pore structure by removing the silica matrix from the silica-MIP composites. With regard to their chromatographic properties and yield of the materials both types of particle were more advantageous compared to irregularly shaped traditional MIPs. Also the work-up time to obtain imprinted spherical particles is greatly reduced compared to traditional methods using polymer monoliths, which have to be ground, sieved and sedimented. Generally, the described method may open new possibilities for synthesis of novel types of imprinted polymer formats such as membranes, bulk polymers, films or in-situ columns using appropriate support or sacrificial materials.

  • 174.
    Zhang, Yan
    et al.
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Angelin, Marcus
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Larsson, Rikard
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Albers, Antonia
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Simons, Adrian
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Tandem driven dynamic self-inhibition of acetylcholinesterase2010Inngår i: Chemical Communications, ISSN 1359-7345, E-ISSN 1364-548X, Vol. 46, nr 44, s. 8457-8459Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    A concept of tandem driven dynamic self-inhibition is demonstrated through dynamic inhibitors of acetylcholinesterase (AChE) using reversible transthiolesterification.

  • 175.
    Zhang, Yan
    et al.
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Hu, Lei
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Double parallel dynamic resolution through lipase-catalyzed asymmetric transformation2013Inngår i: Chemical Communications, ISSN 1359-7345, E-ISSN 1364-548X, Vol. 49, nr 18, s. 1805-1807Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    Dynamic systems based on double parallel reactions have been generated and resolved in situ by secondary lipase-catalyzed asymmetric transformation, resulting in high chemo- and enantioselectivities.

  • 176.
    Zhang, Yan
    et al.
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Jayawardena, H. Surangi N.
    Yan, Mingdi
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi. University of Massachusetts Lowell, MA, United States.
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Enzyme classification using complex dynamic hemithioacetal systems2016Inngår i: Chemical Communications, ISSN 1359-7345, E-ISSN 1364-548X, Vol. 52, nr 28, s. 5053-5056Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    A complex dynamic hemithioacetal system was generated for the evaluation of lipase reactivities in organic media. In combination with pattern recognition methodology, twelve different lipases were successfully classified into four distinct groups following their reaction selectivities and reactivities. A probe lipase was further categorized using the training matrix with predicted reactivity.

  • 177.
    Zhang, Yan
    et al.
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Jayawardena, Surangi
    Yan, Mingdi
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Classification of Lipases Using Pattern Recognition through Transformation of Dynamic Hemithioacetal SystemsArtikkel i tidsskrift (Annet vitenskapelig)
    Abstract [en]

    A complex dynamic hemithioacetal system was generated for the evaluation of lipase reactivities. In combination with pattern recognition methodology, twelve different lipases were successfully classified into three distinct groups following their reaction selectivities and reactivities. A probe lipase was further categorized using the training matrix with predicted reactivity.

  • 178.
    Zhang, Yan
    et al.
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Lipase-Catalyzed Dynamic Systemic Resolution from Reversible Reaction NetworksArtikkel i tidsskrift (Annet vitenskapelig)
    Abstract [en]

    A dynamic system based on a network of multiple reversible reactions has been established. The network was applied to a dynamic systemic resolution protocol based on two kinetically controlled lipase-catalyzed transformations, where two compounds were efficiently selected from a pool of potential products.

  • 179.
    Zhang, Yan
    et al.
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Thiazolidinones Derived from Dynamic Systemic Resolution of Complex Reversible-Reaction Networks2014Inngår i: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 20, nr 12, s. 3288-3291Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    A complex dynamic system based on a network of multiple reversible reactions has been established. The network was applied to a dynamic systemic resolution protocol based on kinetically controlled lipase-catalyzed transformations. This resulted in the formation of cyclized products, where two thiazolidinone compounds were efficiently produced from a range of potential transformations.

  • 180. Zhang, Yan
    et al.
    Sakulsombat, Morakot
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Vongvilai, Pornrapee
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Hu, Lei
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Lipase-mediated dynamic systemic resolution based on single or double reversible reactions2012Inngår i: Abstract of Papers of the American Chemical Society, ISSN 0065-7727, Vol. 244Artikkel i tidsskrift (Annet vitenskapelig)
  • 181.
    Zhang, Yan
    et al.
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Schaufelberger, Fredrik
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Sakulsombat, Morakot
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Liu, Chelsea
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Asymmetric Dynamic Kinetic Resolution for the Synthesis of 1,3-Oxathiolan-5-one DerivativesArtikkel i tidsskrift (Annet vitenskapelig)
    Abstract [en]

    Synthesis of 1,3-oxathiolan-5-one derivatives through dynamic kinetic resolution strategy has been illustrated, resulting in moderate to good enantioselectivities of the final products. In addition, the substrate scope and potential access to lamivudine (3TC) have also been explored.

  • 182.
    Zhang, Yan
    et al.
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Schaufelberger, Fredrik
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Sakulsombat, Morakot
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Liu, Chelsea
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Asymmetric synthesis of 1,3-oxathiolan-5-one derivatives through dynamic covalent kinetic resolution2014Inngår i: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 70, nr 24, s. 3826-3831Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    The asymmetric synthesis of 1,3-oxathiolan-5-one derivatives through an enzyme-catalyzed, dynamic covalent kinetic resolution strategy is presented. Dynamic hemithioacetal formation combined with intramolecular, lipase-catalyzed lactonization resulted in good conversions with moderate to good enantiomeric excess (ee) for the final products. The process was evaluated for different lipase preparations, solvents, bases, and reaction temperatures, where lipase B from Candida antarctica (CAL-B) proved most efficient. The substrate scope was furthermore explored for a range of aldehyde structures, together with the potential access to nucleoside analog inhibitor core structures.

  • 183.
    Zhang, Yan
    et al.
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Vongvilai, Pornrapee
    KTH, Skolan för kemivetenskap (CHE), Kemi.
    Sakulsombat, Morakot
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Fischer, Andreas
    KTH, Skolan för kemivetenskap (CHE), Kemi, Tillämpad fysikalisk kemi.
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Asymmetric Synthesis of Substituted Thiolanes through Domino Thia-Michael-Henry Dynamic Covalent Systemic Resolution using Lipase Catalysis2014Inngår i: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 356, nr 5, s. 987-992Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    Dynamic systems based on consecutive thia-Michael and Henry reactions were generated and transformed using lipase-catalyzed asymmetric transformation. Substituted thiolane structures with three contiguous stereocenters were resolved in the process in high yields and high enantiomeric excesses.

  • 184.
    Zhang, Yan
    et al.
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Vongvilai, Pornrapee
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Sakulsombat, Morakot
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Fischer, Andreas
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Biocatalyzed Dynamic Systemic Domino Thia-Michael--Henry Resolution to Substituted Asymmetric ThiolanesArtikkel i tidsskrift (Annet vitenskapelig)
    Abstract [en]

    Dynamic systems based on consecutive thia-Michael and Henry reactions were generated and transformed using lipase-catalyzed asymmetric transformation. Substituted thiolane structures with three contiguous stereocenters were resolved in the process in high yields and high enantiomeric excesses.

  • 185.
    Zhang, Yan
    et al.
    KTH, Skolan för kemivetenskap (CHE), Kemi.
    Zhang, Yang
    KTH, Skolan för kemivetenskap (CHE), Kemi.
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Asymmetric synthesis of oxazolidin-2-one derivatives through lipase-catalyzed kinetic resolution2014Inngår i: Abstract of Papers of the American Chemical Society, ISSN 0065-7727, Vol. 247Artikkel i tidsskrift (Annet vitenskapelig)
  • 186.
    Zhang, Yan
    et al.
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Zhang, Yang
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Ren, Yansong
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Synthesis of chiral oxazolidinone derivatives through lipase-catalyzed kinetic resolution2015Inngår i: Journal of Molecular Catalysis B: Enzymatic, ISSN 1381-1177, E-ISSN 1873-3158, Vol. 122, s. 29-34Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    The synthesis of enantioenriched oxazolidinone derivatives through lipase-catalyzed kinetic resolution is described. The synthesis comprised a two-step, cascade acylation in one pot, resulting in a range of oxazolidinone derivatives in good yields and excellent enantiopurities.

  • 187.
    Zhang, Yang
    et al.
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Karalius, Antanas
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Yan, Mingdi
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Kinetics and Thermodynamics of Dynamic Nitroaldol Systems in Neutral Aqueous MediaManuskript (preprint) (Annet vitenskapelig)
  • 188.
    Zhang, Yang
    et al.
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Xie, Sheng
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Yan, Mingdi
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Dynamic Covalent Chemistry of Aldehyde Enamines: Bi(III) and Sc(III) catalysis of amine-enamine exchangeManuskript (preprint) (Annet vitenskapelig)
  • 189.
    Zhang, Yang
    et al.
    KTH, Skolan för kemivetenskap (CHE), Kemiteknik, Energiprocesser.
    Xie, Sheng
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Yan, Mingdi
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Dynamic Covalent Chemistry of Aldehyde Enamines: Bi-III- and Sc-III-Catalysis of Amine-Enamine Exchange2017Inngår i: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 23, nr 49, s. 11908-11912Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    The dynamic exchange of enamines from secondary amines and enolizable aldehydes has been demonstrated in organic solvents. The enamine exchange with amines was efficiently catalyzed by Bi(OTf)(3) and Sc(OTf)(3) (2mol%) and the equilibria (60mm) could be attained within hours at room temperature. The formed dynamic covalent systems displayed high stabilities in basic environment with <2% by-product formation within one week after complete equilibration. This study expands the scope of dynamic C-N bonds from imine chemistry to enamines, enabling further dynamic methodologies in exploration of this important class of structures in systems chemistry.

  • 190.
    Zhang, Yang
    et al.
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Xie, Sheng
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Yan, Mingdi
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Enzyme- and Ruthenium-Catalyzed Dynamic Kinetic Resolution Involving Cascade Alkoxycarbonylations for Asymmetric Synthesis of 5-Substituted N-AryloxazolidinonesManuskript (preprint) (Annet vitenskapelig)
  • 191.
    Zhang, Yang
    et al.
    KTH, Skolan för kemi, bioteknologi och hälsa (CBH), Kemiteknik, Energiprocesser.
    Xie, Sheng
    KTH, Skolan för kemi, bioteknologi och hälsa (CBH), Kemi, Organisk kemi.
    Yan, Mingdi
    KTH, Skolan för kemi, bioteknologi och hälsa (CBH), Kemi, Organisk kemi.
    Ramström, Olof
    KTH, Skolan för kemi, bioteknologi och hälsa (CBH), Kemi, Organisk kemi.
    Enzyme- and ruthenium-catalyzed dynamic kinetic resolution involving cascade alkoxycarbonylations for asymmetric synthesis of 5-Substituted N-Aryloxazolidinones2019Inngår i: Molecular Catalysis, ISSN 2468-8231, Vol. 470, s. 138-144Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    AAsymmetric synthesis of N-aryloxazolidinones via dynamic kinetic resolution was developed. A ruthenium-based catalyst was used in the racemization of beta-anilino alcohols, while Candida antarctica lipase B (CAL-B) was applied for two selective alkoxycarbonylations operating in cascade. Various N-aryloxazolidinone derivatives were obtained in high yields and good enantiopurities.

  • 192.
    Zhang, Yang
    et al.
    KTH, Skolan för kemivetenskap (CHE), Kemi.
    Zhang, Yan
    KTH, Skolan för kemivetenskap (CHE), Kemi.
    Xie, Sheng
    KTH, Skolan för kemivetenskap (CHE), Kemi.
    Yan, Mingdi
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Lipase-catalyzed kinetic resolution of 3-phenyloxazolidin-2-one derivatives: Cascade O- and N-alkoxycarbonylations2016Inngår i: Catalysis communications, ISSN 1566-7367, E-ISSN 1873-3905, Vol. 82, s. 11-15Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    A lipase-catalyzed, cascade kinetic resolution protocol has been established for the synthesis of 3-phenyloxazolidin-2-one derivatives with up to excellent enantioselectivities (95% ee). Candida antarctica lipase B showed high catalytic activity and stereoselectivity in sequential O- and N-alkoxycarbonylation processes.

  • 193.
    Zhang, Yang
    et al.
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Zhang, Yan
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Xie, Sheng
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Yan, Mingdi
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Lipase-Catalyzed Kinetic Resolution of 3-Phenyloxazolidin-2-one Derivatives: CascadeO‐ and N‐AlkoxycarbonylationsManuskript (preprint) (Annet vitenskapelig)
  • 194.
    Zhou, Juan
    et al.
    KTH, Skolan för kemivetenskap (CHE), Kemi.
    Butchosa, Nuria
    KTH, Skolan för kemivetenskap (CHE), Fiber- och polymerteknik.
    Jayawardena, H. Surangi N.
    Zhou, Qi
    KTH, Skolan för bioteknologi (BIO), Glykovetenskap. KTH, Skolan för kemivetenskap (CHE), Centra, Wallenberg Wood Science Center.
    Yan, Mingdi
    KTH, Skolan för kemivetenskap (CHE), Kemi.
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Glycan-Functionalized Fluorescent Chitin Nanocrystals for Biorecognition Applications2014Inngår i: Bioconjugate chemistry, ISSN 1043-1802, E-ISSN 1520-4812, Vol. 25, nr 4, s. 640-643Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    A new platform based on chitin nanocrystals has been developed for biorecognition applications. TEMPO-oxidized chitin nanocrystals (TCNs) were labeled with a fluorescent imidazoisoquinolinone dye, and simultaneously conjugated with carbohydrate ligands, resulting in dually functionalized TCNs. The biorecognition properties of the nanocrystals were probed with lectins and bacteria, resulting in selective interactions with their corresponding cognate carbohydrate-binding proteins, as visualized by optical, fluorescence, STEM, and TEM imaging. This represents a new approach to multifunctional nanomaterials based on naturally occurring polymers, holding high potential for biomedical applications.

  • 195.
    Zhou, Juan
    et al.
    KTH, Skolan för kemivetenskap (CHE), Kemi.
    Butchosa, Núria
    KTH, Skolan för kemivetenskap (CHE), Fiber- och polymerteknologi.
    Jayawardena, H. Surangi N.
    University of Massachusetts, United States .
    Park, JaeHyeung
    University of Massachusetts, United States .
    Zhou, Qi
    KTH, Skolan för kemivetenskap (CHE), Centra, Wallenberg Wood Science Center. KTH, Skolan för bioteknologi (BIO), Centra, Albanova VinnExcellence Center for Protein Technology, ProNova.
    Yan, Mingdi
    KTH, Skolan för kemivetenskap (CHE), Kemi. University of Massachusetts, United States .
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi.
    Synthesis of Multifunctional Cellulose Nanocrystals for Lectin Recognition and Bacterial Imaging2015Inngår i: Biomacromolecules, ISSN 1525-7797, E-ISSN 1526-4602, Vol. 16, nr 4, s. 1426-1432Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    Multifunctional cellulose nanocrystals have been synthesized and applied as a new type of glyconanomaterial in lectin binding and bacterial imaging. The cellulose nanocrystals were prepared by TEMPO-mediated oxidation and acidic hydrolysis, followed by functionalization with a quinolone fluorophore and carbohydrate ligands. The cellulose nanocrystals were subsequently applied in interaction studies with carbohydrate-binding proteins and in bacterial imaging. The results show that the functional cellulose nanocrystals could selectively recognize the corresponding cognate lectins. In addition, mannosylated nanocrystals were shown to selectively interact with FimH-presenting E. coli, as detected by TEM and confocal fluorescence microscopy. These glyconanomaterials provide a new application of cellulose nanocrystals in biorecognition and imaging.

  • 196.
    Zhou, Juan
    et al.
    KTH, Skolan för kemivetenskap (CHE), Kemi.
    Hao, Nanjing
    De Zoyza, Thareendra
    Yan, Mingdi
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi. University of Massachusetts, United States.
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Lectin-gated, mesoporous, photofunctionalized glyconanoparticles for glutathione-responsive drug delivery2015Inngår i: Chemical Communications, ISSN 1359-7345, E-ISSN 1364-548X, Vol. 51, nr 48, s. 9833-9836Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    A stimuli-responsive drug delivery system based on fluorescent, lectin-gated, mesoporous glyconanoparticles has been developed and evaluated in normal- and cancer lung epithelial cells. The gating process proved efficient, exhibiting good sealing properties in the absence of the glutathione redox trigger, avoiding premature release in normal cells. In the presence of higher levels of glutathione in cancer cells, the lectin gate was rapidly opened and the anticancer drug released.

  • 197.
    Zhou, Juan
    et al.
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Jayawardana, Kalana
    University of Massachusetts, United States .
    Kong, Na
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Ren, Yansong
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Hao, Nanjing
    Yan, Mingdi
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi. University of Massachusetts, United States .
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Trehalose-Conjugated Mesoporous Silica Nanoparticles for Efficient Delivery of Isoniazid into MycobacteriaManuskript (preprint) (Annet vitenskapelig)
  • 198.
    Zhou, Juan
    et al.
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Jayawardana, Kalana W.
    Kong, Na
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Ren, Yansong
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Hao, Nanjing
    Yan, Mingdi
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi. University of Massachusetts, United States.
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Trehalose-Conjugated, Photofunctionalized Mesoporous Silica Nanoparticles for Efficient Delivery of Isoniazid into Mycobacteria2015Inngår i: ACS BIOMATERIALS-SCIENCE & ENGINEERING, ISSN 2373-9878, Vol. 1, nr 12, s. 1250-1255Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    Glyconanoparticle carriers have been synthesized and efficiently delivered into mycobacteria. Mesoporous silica nanoparticles were functionalized with a,a-trehalose through azide-mediated surface photoligation, and loaded with the antitubercular drug isoniazid. The glyconanoparticles showed high isoniazid loading capacity and higher antimicrobial activity than the free drug.

  • 199.
    Zhou, Juan
    et al.
    KTH, Skolan för kemivetenskap (CHE), Kemi.
    Robles, Nuria
    KTH, Skolan för kemivetenskap (CHE), Fiber- och polymerteknik.
    Zhou, Qi
    KTH, Skolan för bioteknologi (BIO), Glykovetenskap.
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Yan, Mingdi
    Dually functionalized chitin nanocrystals for biorecognition applications2013Inngår i: Abstract of Papers of the American Chemical Society, ISSN 0065-7727, Vol. 246, s. 192-POLY-Artikkel i tidsskrift (Annet vitenskapelig)
  • 200. Zhou, Y.
    et al.
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Dong, H.
    Organosilicon-mediated regioselective acetylation of carbohydrates2012Inngår i: Chemical Communications, ISSN 1359-7345, E-ISSN 1364-548X, Vol. 48, nr 43, s. 5370-5372Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    Organosilicon-mediated, regioselective acetylation of vicinal- and 1,3-diols is presented. Methyl trimethoxysilane or dimethyl dimethoxysilane was first used to form cyclic 1,3,2-dioxasilolane or 1,3,2-dioxasilinane intermediates, and subsequent acetate-catalyzed monoacylation was efficiently performed by addition of acetic anhydride or acetyl chloride under mild conditions. The reaction exhibited high regioselectivity, resulting in the same protection pattern as in organotin-mediated schemes.

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