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  • 1. Andre, Sabine
    et al.
    Pei, Zichao
    KTH, Skolan för kemivetenskap (CHE), Kemi.
    Siebert, Hans-Christian
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi.
    Gabius, Hans-Joachim
    Glycosyldisulfides from Dynamic Combinatorial Libraries as O-Glycoside Mimetics for Plant and Endogenous Lectins: Their Reactivities in Solid-Phase and Cell Assays and Conformational Analysis by Molecular Dynamics Simulations2006Inngår i: Bioorganic & Medicinal Chemistry, ISSN 0968-0896, Vol. 14, s. 6314-6326Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    Dynamic combinatorial library design exploiting the thiol-disulfide exchange readily affords access to glycosyldisulfides. In order to reveal lectin-binding properties of this type of non-hydrolyzable sugar derivative, libraries originating from a mixture of common building blocks of natural glycans and thiocompounds were tested against three plant agglutinins with specificity to galactose, fucose or N-acetylgalactosamine, respectively, in a solid-phase assay. Extent of lectin binding to matrix-immobilized neoglycoprotein presenting the cognate sugar could be reduced, and evidence for dependence on type of carbohydrate was provided by dynamic deconvolution. Glycosyldisulfides also maintained activity in assays of increased physiological relevance, that is, using native tumor cells and also adding to the test panel an endogenous lectin (galectin-3) involved in tumor spread and cardiac dysfunction. N-Acetylgalactosamine was pinpointed as the most important building block of libraries for the human lectin and the digalactoside as most potent compound acting on the toxic mistletoe agglutinin which is closely related to the biohazard ricin. Because this glycosyldisulfide, which even surpasses lactose in inhibitory capacity, rivals thiodigalactoside as inhibitor, their degrees of intramolecular flexibility were comparatively analyzed by computational calculations. Molecular dynamics runs with explicit consideration of water molecules revealed a conspicuously high degree of potential for shape alterations by the disulfide's three-bond system at the interglycosidic linkage. The presented evidence defines glycosyldisulfides as biologically active ligands for lectins

  • 2.
    Angelin, Marcus
    et al.
    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.
    Crystallization-induced secondary selection from a tandem driven dynamic combinatorial resolution process2008Inngår i: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 73, nr 9, s. 3593-3595Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    Crystallization-induced secondary selection from a tandem driven dynamic combinatorial library is presented. In a one-pot experiment, an initial nitroaldol equilibrium was kinetically driven by a tandem reaction resulting in a subsequent dynamic library of diastereoisomers. This library was then further driven by a phase change, resulting in amplification and isolation of a highly diastereomerically enriched and synthetically interesting isoindolinone.

  • 3. Angelin, Marcus
    et al.
    Hermansson, Magnus
    Dong, Hai
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Direct, mild, and selective synthesis of unprotected dialdo-glycosides2006Inngår i: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, nr 19, s. 4323-4326Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    A direct and highly convenient organocatalytic method for the preparation of 1,5-dialdo-pyranosides and 1,4-dialdo-furanosides is presented. The method relies on the chemoselective properties of TEMPO in combination with trichloroisocyanuric acid under very mild, basic conditions. Unprotected glycosides are prepared in a single step in high yields and are efficiently purified with the use of solid-phase imine capture. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006).

  • 4.
    Angelin, Marcus
    et al.
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Larsson, Rikard
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Vongvilai, Pornrapee
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Introducing Dynamic Combinatorial Chemistry: Probing the Substrate Selectivity of Acetylcholinesterase2010Inngår i: Journal of Chemical Education, ISSN 0021-9584, E-ISSN 1938-1328, Vol. 87, nr 11, s. 1248-1251Artikkel i tidsskrift (Fagfellevurdert)
  • 5.
    Angelin, Marcus
    et al.
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Larsson, Rikard
    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.
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Dynamic combinatorial resolution2009Inngår i: Dynamic Combinatorial Chemistry: In Drug Discovery, Bioorganic Chemistry, and Materials Science / [ed] Miller, B., John Wiley & Sons, 2009, s. 169-200Kapittel i bok, del av antologi (Fagfellevurdert)
  • 6.
    Angelin, Marcus
    et al.
    KTH, Skolan för kemivetenskap (CHE), Kemi.
    Rahm, Martin
    KTH, Skolan för kemivetenskap (CHE), Kemi.
    Fischer, Andreas
    KTH, Skolan för kemivetenskap (CHE), Kemi.
    Brinck, Tore
    KTH, Skolan för kemivetenskap (CHE), Kemi.
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi.
    Diastereoselective One-Pot Tandem Synthesis of 3-Substituted Isoindolinones: A Mechanistic Investigation2010Inngår i: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 75, nr 17, s. 5882-5887Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    The mechanism of a base-catalyzed one-pot reaction of 2-cyanobenzaldehyde and primary nitroalkanes, to produce 3-substituted isoindolinones, has been investigated. A route starting with a nitroaldol (Henry) reaction, followed by a subsequent cyclization and rearrangement, was supported by intermediate analogue synthesis and DFT calculations. Direct diastereoselective crystallization from the reaction mixture was also achieved and studied for a number of substrates. Furthermore, the 3-substituted isoindolinones are an interesting group of compounds, both present important natural products, as well as being precursors to other valuable building blocks.

  • 7.
    Angelin, Marcus
    et al.
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Making a Chemical Rainbow2010Inngår i: Journal of Chemical Education, ISSN 0021-9584, E-ISSN 1938-1328, Vol. 87, nr 5, s. 504-506Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    In this laboratory experiment, high school students are challenged to prepare a six-layered chemical "rainbow" in a test tube. Students start with six unknown, colorless liquids and six pigments ranging from violet to red. The experiment is problem based and forces the students to apply their knowledge of solubility and density and combine it with creative and critical thinking to come up with a successful strategy to make the rainbow. This is followed by experimental testing to find the unique solution. Finally, coloring and correct layering of the liquids produces the final and aesthetically pleasing result, a chemical rainbow.

  • 8.
    Angelin, Marcus
    et al.
    KTH, Skolan för kemivetenskap (CHE), Kemi.
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Where's Ester? A Game That Seeks the Structures Hiding Behind the Trivial Names2010Inngår i: Journal of Chemical Education, ISSN 0021-9584, E-ISSN 1938-1328, Vol. 87, nr 4, s. 406-407Artikkel i tidsskrift (Fagfellevurdert)
  • 9.
    Angelin, Marcus
    et al.
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Vongvilai, Pornrapee
    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.
    Crystallization Driven Asymmetric Synthesis of Pyridine β-Nitroalcoholsvia Discovery-Oriented Self-Resolution of a Dynamic System2010Inngår i: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, Vol. 33, s. 6315-6318Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    The study of dynamic nitroaldol systems aided the discovery of a diastereoselective crystallization process through amplification of 2-nitro-1-(pyridine-4-yl)propan-1-ol. The phenomenon was further developed into an effective procedure for asymmetic synthesis of pyridine-nitroalcohols and several substrates were screened to this end. These results demonstrate how work with larger dynamic systems facilitates and increases the likelihood of serendipitous discoveries.

  • 10.
    Angelin, Marcus
    et al.
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Vongvilai, Pornrapee
    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.
    Tandem driven dynamic combinatorial resolution via Henry–iminolactone rearrangement2008Inngår i: ChemComm, ISSN 1359-7345, s. 768-770Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    An unexplored type of tandem reaction is used to kinetically resolve a dynamic combinatorial library resulting in quantitative amplification of an interesting 3-substituted isoindolinone.

  • 11. Bunyapaiboonsri, T.
    et al.
    Ramstrom, H.
    Ramström, Olof
    KTH, Tidigare Institutioner                               , Kemi.
    Haiech, J.
    Lehn, J. M.
    Generation of Bis-cationic heterocyclic inhibitors of Bacillus subtilis HPr kinase/phosphatase from a ditopic dynamic combinatorial library2003Inngår i: Journal of Medicinal Chemistry, ISSN 0022-2623, E-ISSN 1520-4804, Vol. 46, nr 26, s. 5803-5811Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    Ditopic dynamic combinatorial. libraries were generated and screened toward inhibition of the bifunctional enzyme HPr kinase/phosphatase from Bacillus subtilis. The libraries were composed of all possible combinations resulting from the dynamic interconversion of 16 hydrazides and five monoaldehyde or dialdehyde building blocks, resulting in libraries containing up to 440 different constituents. Of all possible acyl hydrazones formed, active compounds containing two terminal cationic heterocyclic recognition groups separated by a spacer of appropriate structure could be rapidly identified using a dynamic deconvolution procedure. Thus, parallel testing of sublibraries where one specific component was excluded basically revealed all the essential components. A potent ditopic inhibitor, based on 2-amino-benzimidazole, was identified from the process.

  • 12. Bunyapaiboonsri, T.
    et al.
    Ramström, Olof
    KTH, Tidigare Institutioner                               , Kemi.
    Lohmann, S.
    Lehn, J. M.
    Peng, L.
    Goeldner, M.
    Dynamic deconvolution of a pre-equilibrated dynamic combinatorial library of acetylcholinesterase inhibitors2001Inngår i: ChemBioChem (Print), ISSN 1439-4227, E-ISSN 1439-7633, Vol. 2, nr 6, s. 438-444Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    A dynamic combinatorial library composed of interconverting acylhydrazones has been generated and screened towards inhibition of acetylcholinesterase from the electric ray Torpedo marmorata. Starting from a small set (13) of initial hydrazide and aldehyde building blocks, a library containing possibly 66 different species was obtained in a single operation. Of all possible acylhydrazones formed, active compounds containing two terminal cationic recognition groups separated by an appropriate distance, permitting two-site binding, could be rapidly identified by using a dynamic deconvolution-screening procedure, based on the sequential removal of starting building blocks. A very potent bis-pyridinium inhibitor (K (i)= 1.09 nM, alphaK(i) = 2.80 nM) was selected from the process and the contribution of various structural features to inhibitory potency was evaluated.

  • 13.
    Caraballo, Remi
    et al.
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Rahm, Martin
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Vongvilai, Pornrapee
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Brinck, Tore
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Phosphine-catalyzed disulfide metathesis2008Inngår i: Chemical Communications, ISSN 1359-7345, E-ISSN 1364-548X, nr 48, s. 6603-6605Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    The reaction between disulfides and phosphines generates a reversible disulfide metathesis process.

  • 14.
    Caraballo, Rémi
    et al.
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Deng, Lingquan
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Amorim, Luis
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Brinck, Tore
    KTH, Skolan för kemivetenskap (CHE), Kemi, Fysikalisk kemi.
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    pH-Dependent Mutarotation of 1-Thioaldoses in Water. Unexpected Behavior of (2S)-D-Aldopyranoses2010Inngår i: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 75, nr 18, s. 6115-6121Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    The pH-dependent mutarotation of 1-thioaldopyranoses in aqueous media has been investigated. Anomerization readily occurred at lower and neutral pH for all aldopyranoses studied, whereas mainly for (2S)-D-aldopyranoses at higher pH. 1-Thio-D-mannopyranose and 1-thio-D-altropyranose showed very strong pH dependence where the anomeric equilibrium ratios changed dramatically from a preference for the beta-anomer at lower pH to the alpha-anomer at higher pH.

  • 15.
    Caraballo, Rémi
    et al.
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Dong, Hai
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Ribeiro, Joao P.
    Jimenez-Barbero, Jesus
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Direct STD NMR Identification of beta-Galactosidase Inhibitors from a Virtual Dynamic Hemithioacetal System2010Inngår i: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 49, nr 3, s. 589-593Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

     The formation of a dynamic hemithioacetal system and its application toward the discovery of ß-galactosidase inhibitors were successfully investigated. The designed dynamic system, which has a virtual character in neutral aqueous media, was subjected to a direct in situ identification of the best inhibitors by 1H STD NMR spectroscopy (ONPC : o-nitrophenyl-β-galactopyranoside).

  • 16.
    Caraballo, Rémi
    et al.
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Sakulsombat, Morakot
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Phosphine-Mediated Disulfide Metathesis in Aqueous Media2010Inngår i: Chemical Communications, ISSN 1359-7345, E-ISSN 1364-548X, Vol. 46, nr 44, s. 8469-8471Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    Dynamic carbohydrate systems have been efficiently generated through phosphine-mediated disulfide metathesis in aqueous media. The protein compatibility and binding features of the dynamic systems were demonstrated in situ using H-1 STD NMR.

  • 17.
    Caraballo, Rémi
    et al.
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Sakulsombat, Morakot
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Towards Dynamic Drug Design: Identification and Optimization of β-Galactosidase Inhibitors from a Dynamic Hemithioacetal System2010Inngår i: ChemBioChem (Print), ISSN 1439-4227, E-ISSN 1439-7633, Vol. 11, nr 11, s. 1600-1606Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    A discovery strategy relying on the identification of fragments through resolution of a constitutional dynamic system, coupled to subsequent static ligand design and optimization, is demonstrated. The strategic design and synthesis of the best molecular fragments identified from a dynamic hemithioacetal system into static ligand structures yielded a range of -galactosidase inhibitors. Two series of structures mimicking the hemithioacetal motif were envisaged: thioglycosides and C-glycosides. Inhibition studies provided important structural information for the two groups, and 1-thiobenzyl--D-galactopyranoside demonstrated the best inhibitory effects.

  • 18. Chen, Xuan
    et al.
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Yan, Mingdi
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi. University of Massachusetts Lowell, United States .
    Glyconanomaterials: Emerging applications in biomedical research2014Inngår i: Nano Reseach, ISSN 1998-0124, E-ISSN 1998-0000, Vol. 7, nr 10, s. 1381-1403Artikkel, forskningsoversikt (Fagfellevurdert)
    Abstract [en]

    Carbohydrates constitute the most abundant organic matter in nature, serving as structural components and energy sources, and mediating a wide range of cellular activities. The emergence of nanomaterials with distinct optical, magnetic, and electronic properties has witnessed a rapid adoption of these materials for biomedical research and applications. Nanomaterials of various shapes and sizes having large specific surface areas can be used as multivalent scaffolds to present carbohydrate ligands. The resulting glyconanomaterials effectively amplify the glycan-mediated interactions, making it possible to use these materials for sensing, imaging, diagnosis, and therapy. In this review, we summarize the synthetic strategies for the preparation of various glyconanomaterials. Examples are given where these glyconanomaterials have been used in sensing and differentiation of proteins and cells, as well as in imaging glycan-medicated cellular responses.

  • 19.
    Deng, Lingquan
    et al.
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Norberg, Oscar
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Uppalapati, Suji
    Yan, Mingdi
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Stereoselective synthesis of light-activatable perfluorophenylazide-conjugated carbohydrates for glycoarray fabrication and evaluation of structural effects on protein binding by SPR imaging2011Inngår i: Organic and biomolecular chemistry, ISSN 1477-0520, E-ISSN 1477-0539, Vol. 9, nr 9, s. 3188-3198Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    A series of light-activatable perfluorophenylazide (PFPA)-conjugated carbohydrate structures have been synthesized and applied to glycoarray fabrication. The glycoconjugates were structurally varied with respect to anomeric attachment, S-, and O-linked carbohydrates, respectively, as well as linker structure and length. Efficient stereoselective synthetic routes were developed, leading to the formation of the PFPA-conjugated structures in good yields over few steps. The use of glycosyl thiols as donors proved especially efficient and provided the final compounds in up to 70% total yield with high anomeric purities. PFPA-based photochemistry was subsequently used to generate carbohydrate arrays on a polymeric surface, and surface plasmon resonance imaging (SPRi) was applied for evaluation of carbohydrate-protein interactions using the plant lectin Concanavalin A (Con A) as a probe. The results indicate better performance and equal efficiency of S-and O-linked structures with intermediate linker length.

  • 20.
    Deng, Lingquan
    et al.
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Wang, Xin
    Uppalapati, Suji
    Norberg, Oscar
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Dong, Hai
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Joliton, Adrien
    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.
    Stereocontrolled 1-S-glycosylation and comparative binding studies of photoprobe-thiosaccharide conjugates with their O-linked analogs2013Inngår i: Pure and Applied Chemistry, ISSN 0033-4545, E-ISSN 1365-3075, Vol. 85, nr 9, s. 1789-1801Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    The use of thioglycosides and other glycan derivatives with anomeric sulfur linkages is gaining increasing interest, both in synthesis and in various biological contexts. Herein, we demonstrate the occurrence and circumvention of anomerization during 1-S-glycosylation reactions, and present highly efficient and stereocontrolled syntheses of a series of photoprobe-thiosaccharide conjugates. Mutarotation of glycosyl thiols proved to be the origin of the anomeric mixtures formed, and kinetic effects could be used to circumvent anomerization. The synthesized carbohydrate conjugates were then evaluated by both solution- and solid-phase-based techniques. Both binding results showed that the S-linked glycosides interact with their cognate lectins comparably to the corresponding O-analogs in the present cases, thus demonstrating the reliability of the solid-support platform built upon our photo-initiated carbohydrate immobilization method for probing protein bindings, and showing the potential of combining these two means for studying carbohydrate-protein inter-actions.

  • 21.
    Dong, Hai
    et al.
    KTH, Skolan för kemivetenskap (CHE), Kemi.
    Deng, Lingquan
    KTH, Skolan för kemivetenskap (CHE), Kemi.
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi.
    Control of the Ambident Reactivity of the Nitrite Ion inCarbohydrate EpimerizationManuskript (Annet vitenskapelig)
  • 22.
    Dong, Hai
    et al.
    KTH, Skolan för kemivetenskap (CHE), Kemi.
    Pei, Zhichao
    KTH, Skolan för kemivetenskap (CHE), Kemi.
    Angelin, Marcus
    KTH, Skolan för kemivetenskap (CHE), Kemi.
    Byström, Styrbjörn
    KTH, Skolan för kemivetenskap (CHE), Kemi.
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi.
    Efficient Synthesis of β-D-Mannosides and β-D-Talosides by Double Parallel or Double Serial Inversion2007Inngår i: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 72, nr 10, s. 3694-3701Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    A neighboring equatorial ester group plays a highly important role in the Lattrell-Dax (nitrite-mediated) carbohydrate epimerization reaction, inducing the formation of inversion compounds in good yields. On the basis of this effect, efficient synthetic routes to beta-D-mannosides and beta-D-talosides, from the corresponding beta-D-galactosides and beta-D-glucosides, have been designed. The present routes are based on multiple regioselective acylation via the respective stannylene intermediates, followed by inversions to the corresponding manno- and talopyranoside structures by nitrite or acetate substitution. It was found that the ester group was able to induce the inversion of its two neighboring groups in high yields following either a double parallel or a double serial inversion process. By combination of direct inversion, and neighboring- as well as remote-group participation, several beta-D-mannoside and beta-D-taloside derivatives were very conveniently obtained in good yields.

  • 23.
    Dong, Hai
    et al.
    KTH, Skolan för kemivetenskap (CHE), Kemi.
    Pei, Zhichao
    KTH, Skolan för kemivetenskap (CHE), Kemi.
    Byström, Styrbjörn
    KTH, Skolan för kemivetenskap (CHE), Kemi.
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi.
    Reagent-dependent regioselective control in multiple carbohydrate esterifications2007Inngår i: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 72, nr 4, s. 1499-1502Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    Regioselective control in organotin-mediated multiple acylation of carbohydrates is presented. The acylation reagent could be efficiently used to direct the product formation. Reagent-dependent thermodynamic and kinetic control and dynamic assistance mechanisms are suggested, resulting in the efficient preparation of building blocks that normally require many steps with traditional synthesis.

  • 24.
    Dong, Hai
    et al.
    KTH, Skolan för kemivetenskap (CHE), Kemi.
    Pei, Zhichao
    KTH, Skolan för kemivetenskap (CHE), Kemi.
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi.
    Stereospecific Ester Activation in Nitrite-Mediated Carbohydrate Epimerization2006Inngår i: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 71, nr 8, s. 3306-3309Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    The Lattrell-Dax method of nitrite-mediated substitution of carbohydrate triflates is an efficient method to generate structures of inverse configuration. In the present study, epimerization of gluco- and galactopyranoside derivatives to the corresponding allo- and gulopyranoside structures by triflation/nitrite treatment has been investigated. It was found that a neighboring ester group was essential for the reactivity of the nitrite-mediated triflate, inversion. Furthermore, a good inversion yield also depended on the relative configuration of the neighboring ester group to the triflate. Only with the ester group in the equatorial position, whatever the configuration of the triflate, did the reaction proceed smoothly, whereas a neighboring axial ester group proved largely inefficient. The results were subsequently used to predict the inversion of glucopyranoside derivatives to the mannopyranoside epimers.

  • 25.
    Dong, Hai
    et al.
    KTH, Skolan för kemivetenskap (CHE), Kemi.
    Pei, Zhichao
    KTH, Skolan för kemivetenskap (CHE), Kemi.
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi.
    Supramolecular activation in triggered cascade inversion2008Inngår i: Chemical Communications, ISSN 1359-7345, E-ISSN 1364-548X, s. 1359-1361Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    An unexpected activation effect from combinations of anionic reagent and amine base resulted in dramatic rate enhancements in multiple carbohydrate cascade inversion.

  • 26.
    Dong, Hai
    et al.
    KTH, Skolan för kemivetenskap (CHE), Kemi.
    Rahm, Martin
    KTH, Skolan för kemivetenskap (CHE), Kemi.
    Brinck, Tore
    KTH, Skolan för kemivetenskap (CHE), Kemi.
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi.
    Supramolecular Control in Carbohydrate Epimerization: Discovery of a New Anion Host−Guest System2008Inngår i: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 130, s. 15270-15271Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    A new anion-carbohydrate recognition system is described. Pyranosides with axial protons in 1-, 3-, and 5-position proved efficient, forming relatively strong complexes between the anion and the B-face of the carbohydrate. This system could furthermore be used in supramolecular control in Lattrell-Dax epimerization reactions, leading to either activation or deactivation effects.

  • 27.
    Dong, Hai
    et al.
    KTH, Skolan för kemivetenskap (CHE), Kemi.
    Rahm, Martin
    KTH, Skolan för kemivetenskap (CHE), Kemi.
    Thota, Niranjan
    KTH, Skolan för kemivetenskap (CHE), Kemi.
    Deng, Lingquan
    KTH, Skolan för kemivetenskap (CHE), Kemi.
    Brinck, Tore
    KTH, Skolan för kemivetenskap (CHE), Kemi, Tillämpad fysikalisk kemi.
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Control of the ambident reactivity of the nitrite ion2013Inngår i: Organic and biomolecular chemistry, ISSN 1477-0520, E-ISSN 1477-0539, Vol. 11, nr 4, s. 648-653Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    In previous studies, it was reported that a neighbouring equatorial ester group is essential for a good yield of nitrite-mediated triflate inversion, whereas with neighbouring benzyl ether groups or axial ester groups, mixtures are generally produced. In the present study, the origin of this difference was addressed. The ambident reactivity of the nitrite ion has been found to be the cause of the complex product formation observed, which can be controlled by a neighbouring equatorial ester group. Both N-attack and O-attack occur in the absence of the ester group, whereas O-attack is favoured in its presence. A neighbouring group assistance mechanism is proposed, in addition to steric effects, based on secondary interactions between the neighbouring ester group and the incoming nucleophile. High-level quantum mechanical calculations were carried out in order to delineate this effect. The theoretical results are in excellent agreement with experiments, and suggest a catalytic role for the neighbouring equatorial ester group.

  • 28.
    Dong, Hai
    et al.
    KTH, Skolan för kemivetenskap (CHE), Kemi.
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi.
    Enhanced Basicity by Supramolecular Anion ActivationManuskript (Annet vitenskapelig)
  • 29. Dong, Hai
    et al.
    Zhou, Yixuan
    Pan, Xiaoliang
    Cui, Fengchao
    Liu, Wei
    Liu, Jingyao
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Stereoelectronic Control in Regioselective Carbohydrate Protection2012Inngår i: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 77, nr 3, s. 1457-1467Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    Organotin-mediated regioselective protection has been extensively used in organic synthesis for many years. However, the mechanistic origin of the resulting regioselectivity is still not clear. By the comparison of the steric and stereoelectronic effects controlling the geometry of five-membered rings formed from neighboring group participation, from intramolecular acyl group migration, or from orthoester transesterification on pyranoside rings, a theory on the pattern resulting from the reaction with dibutyltin oxide is presented. It is thus suggested that the regioselectivity of organotin-mediated protection is controlled by analogous steric and stereoelectronic effects as in neighboring group participation and acyl group migration, mainly dependent on the stereoelectronic effects of the pyranoside itself, and not related to complex stannylene structures. An organotin protection mechanism is also suggested, emanating from steric and stereoelectronic effects, nucleophilicity, and organotin acyl migration.

  • 30.
    Duner, Gunnar
    et al.
    KTH, Skolan för kemivetenskap (CHE), Kemi, Yt- och korrosionsvetenskap.
    Anderson, Henrik
    Pei, Zhichao
    Ingemarsson, Bjorn
    Aastrup, Teodor
    Ramstrom, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Signal enhancement in ligand-receptor interactions using dynamic polymers at quartz crystal microbalance sensors2016Inngår i: The Analyst, ISSN 0003-2654, E-ISSN 1364-5528, Vol. 141, nr 13, s. 3993-3996Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    The signal enhancement properties of QCM sensors based on dynamic, biotinylated poly(acrylic acid) brushes has been studied in interaction studies with an anti-biotin Fab fragment. The poly (acrylic acid) sensors showed a dramatic increase in signal response with more than ten times higher signal than the carboxyl-terminated self-assembled monolayer surface.

  • 31.
    Dunér, Gunnar
    et al.
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Anderson, Henrik
    Ingemarsson, Björn
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Determination of Dissociation Constants on Quartz Crystal Microbalance Surfaces by Polymer Signal EnhancementManuskript (preprint) (Annet vitenskapelig)
  • 32.
    Dunér, Gunnar
    et al.
    KTH, Skolan för kemivetenskap (CHE), Kemi.
    Anderson, Henrik
    Myrskog, Annica
    Hedlund, Maria
    Aastrup, Teodor
    KTH, Skolan för kemivetenskap (CHE), Kemi.
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Surface-confined photopolymerization of pH-responsive acrylamide/acrylate brushes on polymer thin films2008Inngår i: Langmuir, ISSN 0743-7463, E-ISSN 1520-5827, Vol. 24, nr 14, s. 7559-7564Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    Dynamic acrylamide/acrylate polymeric brushes were synthesized at gold-plated quartz crystal surfaces. The crystals were initially coated with polystyrene-type thin films, derivatized with photolabile iniferter groups, and subsequently subjected to photoinitiated polymerization in acrylamide/acrylate monomer feeds. This surface-confined polymerization method enabled direct photocontrol over the polymerization, as followed by increased frequency responses of the crystal oscillations in a quartz crystal microbalance (QCM). The produced polymer layers were also found to be highly sensitive to external acid/base stimuli. Large oscillation frequency shifts were detected when the brushes were exposed to buffer solutions of different pH. The dynamic behavior of the resulting polymeric brushes was evaluated, and the extent of expansion and contraction of the films was monitored by the QCM setup in situ in real time. The resulting responses were rapid, and the effects were fully reversible. Low pH resulted in full contractions of the films, whereas higher pH yielded maximal expansion in order to minimize repulsion around the charged acrylate centers. The surfaces also proved to be very robust because the responsiveness was reproducible over many cycles of repeated expansion and contraction. Using ellipsometry, copolymer layers were estimated to be similar to 220 nm in a collapsed state and similar to 340 nm in the expanded state, effectively increasing the thickness of the film by 55%.

  • 33.
    Dunér, Gunnar
    et al.
    KTH, Skolan för kemivetenskap (CHE), Kemi.
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi.
    Signal Enhancement in Ligand-Receptor Interactions using Dynamic Polymers at Quartz Crystal Microbalance SurfacesManuskript (preprint) (Annet vitenskapelig)
  • 34.
    Dunér, Gunnar
    et al.
    KTH, Skolan för kemivetenskap (CHE), Kemi, Tillämpad fysikalisk kemi.
    Thormann, Esben
    KTH, Skolan för kemivetenskap (CHE), Kemi, Yt- och korrosionsvetenskap.
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Claesson, Per M.
    KTH, Skolan för kemivetenskap (CHE), Kemi, Yt- och korrosionsvetenskap.
    Dédinaité, Andra
    KTH, Skolan för kemivetenskap (CHE), Kemi, Tillämpad fysikalisk kemi.
    Determination of grafting density of poly(acrylic acid) in a grafting: from approach using quartz crystal microbalance with dissipationManuskript (preprint) (Annet vitenskapelig)
  • 35.
    Dunér, Gunnar
    et al.
    KTH, Skolan för kemivetenskap (CHE), Kemi, Yt- och korrosionsvetenskap.
    Thormann, Esben
    KTH, Skolan för kemivetenskap (CHE), Kemi, Yt- och korrosionsvetenskap.
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Dédinaité, Andra
    KTH, Skolan för kemivetenskap (CHE), Kemi, Yt- och korrosionsvetenskap.
    Friction between Surfaces—Polyacrylic Acid Brush and Silica—Mediated by Calcium Ions2010Inngår i: Journal of Dispersion Science and Technology, ISSN 0193-2691, E-ISSN 1532-2351, Vol. 31, s. 1285-1287Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    With this letter, we report how friction can be controlled by inducing physical bonds solely within a polyelectrolyte brush layer, while keeping repulsive interactions between the brush layer and the bare surface that slides above. Our results imply that the nature of the bare surface is of minor importance as long as the repulsive surface interaction is maintained.

  • 36.
    Hao, Nanjing
    et al.
    Department of Chemistry, University of Massachusetts, USA.
    Neranon, Kitjanit
    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. Department of Chemistry, University of Massachusetts, USA.
    Glyconanomaterials for biosensing applications2016Inngår i: Biosensors & bioelectronics, ISSN 0956-5663, E-ISSN 1873-4235, Vol. 76, nr 15, s. 113-130Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    Nanomaterials constitute a class of structures that have unique physiochemical properties and are excellent scaffolds for presenting carbohydrates, important biomolecules that mediate a wide variety of important biological events. The fabrication of carbohydrate-presenting nanomaterials, glyconanomaterials, is of high interest and utility, combining the features of nanoscale objects with biomolecular recognition. The structures can also produce strong multivalent effects, where the nanomaterial scaffold greatly enhances the relatively weak affinities of single carbohydrate ligands to the corresponding receptors, and effectively amplifies the carbohydrate-mediated interactions. Glyconanomaterials are thus an appealing platform for biosensing applications. In this review, we discuss the chemistry for conjugation of carbohydrates to nanomaterials, summarize strategies, and tabulate examples of applying glyconanomaterials in in vitro and in vivo sensing applications of proteins, microbes, and cells. The limitations and future perspectives of these emerging glyconanomaterials sensing systems are furthermore discussed.

  • 37. Harnish, B.
    et al.
    Robinson, J. T.
    Pei, Zhichao
    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.
    UV-cross-linked poly(vinylpyridine) thin films as reversibly responsive surfaces2005Inngår i: Chemistry of Materials, ISSN 0897-4756, E-ISSN 1520-5002, Vol. 17, nr 16, s. 4092-4096Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    We report that UV-cross-linked poly(4-vinylpyridine) (P4VP) films acted as reversibly responsive coatings that controlled surface wettability and swelling toward external stimuli: solvent and pH. The polymer films were prepared simply by spin-coating a solution of P4VP followed by UV irradiation. These cross-linked films, when treated with chloroform, showed similar to 31% increase in film thickness whereas films extracted with methylene chloride or n-butanol exhibited a slight decrease. The increase in film thickness was due to the protonation of pyridyl groups by hydrogen chloride resulting from the photodegeneration of chloroform. The film expanded to minimize repulsion around the charged centers. This hypothesis was further confirmed by exposing the cross-linked film to hydrogen chloride vapor. The film expanded similar to 37% whereas no thickness increase was observed for films exposed to ammonia or methanol vapors. The extent of swelling was monitored in situ using a quartz crystal microbalance sensor. Large oscillation frequency shifts were detected when the UV-cross-linked P4VP film was exposed to acidic buffer solutions. The changes were rapid, and the effect was reversible.

  • 38.
    Hu, Lei
    et al.
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Silver-catalyzed dynamic systemic resolution of alpha-iminonitriles in a 1,3-dipolar cycloaddition process2014Inngår i: Chemical Communications, ISSN 1359-7345, E-ISSN 1364-548X, Vol. 50, nr 29, s. 3792-3794Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    A dynamic azomethine ylide system was established using Sc(OTf)(3) and Ag/Taniaphos as catalysts. The system was subsequently kinetically resolved in a tandem 1,3-dipolar cycloaddition process where the silver complex acted as both a reaction catalyst and an external selector, resulting in the formation of an exclusive pyrrolidine product in good yield and enantiopurity.

  • 39.
    Hu, Lei
    et al.
    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.
    Chirality Control in Enzyme-Catalyzed Dynamic Kinetic Resolution of 1,3-Oxathiolanes2015Inngår i: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 80, nr 16, s. 8478-8481Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    The origin of enantioenrichment in enzyme-catalyzed dynamic kinetic resolution of 1,3-oxathiolane derivatives, key intermediates for asymmetric lamivudine synthesis, was elucidated. The chirality control could be determined by chiral HPLC and NOE NMR spectroscopy using a modified 1,3-oxathiolane compound obtained through enzyme-catalyzed selective hydrolysis. Solvent-dependent stereoselectivity was observed under biphasic conditions using different organic solvents with phosphate buffer.

  • 40.
    Hu, Lei
    et al.
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Schaufelberger, Fredrik
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Zhang, Yan
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Efficient asymmetric synthesis of lamivudine via enzymatic dynamic kinetic resolution2013Inngår i: Chemical Communications, ISSN 1359-7345, E-ISSN 1364-548X, Vol. 49, nr 88, s. 10376-10378Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    The anti-HIV nucleoside lamivudine was asymmetrically synthesized in only three steps via a novel surfactant-treated subtilisin Carlsberg-catalyzed dynamic kinetic resolution protocol. The enantiomer of lamivudine could also be accessed using the same protocol catalyzed by Candida antarctica lipase B.

  • 41.
    Hu, Lei
    et al.
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Zhang, Yan
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Asymmetric Synthesis of Lamivudine and its Enantiomer: Mechanism of Chirality Control in Enzyme-Catalyzed 1,3-Oxathiolane Ring Closing ProcessesManuskript (preprint) (Annet vitenskapelig)
  • 42.
    Hu, Lei
    et al.
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Zhang, Yan
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Gelation-Driven Dynamic Systemic Resolution: in situ Generation and Self-Selection of an OrganogelatorManuskript (preprint) (Annet vitenskapelig)
  • 43.
    Hu, Lei
    et al.
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Zhang, Yan
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Lipase-catalyzed asymmetric synthesis of oxathiazinanones through dynamic covalent kinetic resolution2014Inngår i: Organic and biomolecular chemistry, ISSN 1477-0520, E-ISSN 1477-0539, Vol. 12, nr 22, s. 3572-3575Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    A domino addition-lactonization pathway has been applied to a dynamic covalent resolution protocol, leading to efficient oxathiazinanone formation as well as chiral discrimination. A new, double biocatalytic pathway has furthermore been proposed and evaluated where the initial product inhibition could be efficiently circumvented.

  • 44.
    Hu, Lei
    et al.
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Zhang, Yan
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Lipase-Catalyzed Dynamic Kinetic Asymmetric Transformation to OxathiazinanonesArtikkel i tidsskrift (Annet vitenskapelig)
    Abstract [en]

    A domino addition-lactonization pathway has been applied to a dynamic covalent resolution protocol, leading to efficient oxathiazinanone formation as well as chiral discrimination. A new, double biocatalytic pathway has furthermore been proposed and evaluated where initial product inhibition could be efficiently circumvented.

  • 45. Hu, Lei
    et al.
    Zhang, Yang
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Gelation-driven Dynamic Systemic Resolution: in situ Generation and Self-Selection of an Organogelator2015Inngår i: Scientific Reports, ISSN 2045-2322, E-ISSN 2045-2322, Vol. 5, artikkel-id 11065Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    An organogelator was produced and identified from a dynamic imine system, resolved and amplified by selective gelation. The formation of the organogel was monitored in situ by H-1 NMR, showing the existence of multiple reversible reactions operating simultaneously, and the redistribution of the involved species during gelation. The formed organogelator proved effective with a range of organic solvents, including DMSO, toluene, and longer, linear alcohols.

  • 46.
    Kong, Na
    et al.
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Joen, Seaho
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Yan, Mingdi
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Covalent Functionalization of Buckminsterfullerene with Perfluorophenyl Azide by Microwave Irradiation, Photochemical or Thermal ActivationManuskript (preprint) (Annet vitenskapelig)
  • 47.
    Kong, Na
    et al.
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Park, JaeHyeung
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Yan, Mingdi
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Carbohydrate Functionalization of Few-Layer Graphene through Microwave-Assisted Reaction of Perfluorophenyl AzideManuskript (preprint) (Annet vitenskapelig)
  • 48.
    Kong, Na
    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.
    Functionalization of carbon nanomaterials with perfluorophenyl azides and their application in biorecognition2014Inngår i: Abstract of Papers of the American Chemical Society, ISSN 0065-7727, Vol. 247Artikkel i tidsskrift (Annet vitenskapelig)
  • 49.
    Kong, Na
    et al.
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Shimpi, Manishkumar R.
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Park, Jae Hyeung
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Yan, Mingdi
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Carbohydrate conjugation through microwave-assisted functionalization of single-walled carbon nanotubes using perfluorophenyl azides2015Inngår i: Carbohydrate Research, ISSN 0008-6215, E-ISSN 1873-426X, Vol. 405, s. 33-38Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    Carbohydrate-functionalized single-walled carbon nanotubes (SWNTs) were synthesized using microwave-assisted reaction of perfluorophenyl azide with the nanotubes. The results showed that microwave radiation provides a rapid and effective means to covalently attach carbohydrates to SWNTs, producing carbohydrate-SWNT conjugates for biorecognition. The carbohydrate-functionalized SWNTs were furthermore shown to interact specifically with cognate carbohydrate-specific proteins (lectins), resulting in predicted recognition patterns. The carbohydrate-presenting SWNTs constitute a new platform for sensitive protein-or cell recognition, which pave the way for glycoconjugated carbon nanomaterials in biorecognition applications.

  • 50.
    Kong, Na
    et al.
    KTH, Skolan för kemivetenskap (CHE), Kemi.
    Shimpi, Manishkumar
    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.
    Functionalization of carbohydrate-presenting single-walled carbon nanotubes using microwave-assisted phenylnitrene addition and their biorecognition applications2013Inngår i: Abstract of Papers of the American Chemical Society, ISSN 0065-7727, Vol. 245Artikkel i tidsskrift (Annet vitenskapelig)
1234 1 - 50 of 173
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