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  • 1.
    Abellan-Flos, Marta
    et al.
    Univ Namur, Dept Chim, Lab Chim Bioorgan, Rue Bruxelles 61, B-5000 Namur, Belgium.;PSL Univ, CNRS, ESPCI Paris, Mol Macromol Chem & Mat, 10 Rue Vauquelin, F-75005 Paris, France..
    Timmer, Brian J. J.
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry.
    Altun, Samuel
    Attana AB, Bjornnasvagen 21, S-11419 Stockholm, Sweden..
    Aastrup, Teodor
    Attana AB, Bjornnasvagen 21, S-11419 Stockholm, Sweden..
    Vincent, Stephane P.
    Univ Namur, Dept Chim, Lab Chim Bioorgan, Rue Bruxelles 61, B-5000 Namur, Belgium..
    Ramström, Olof
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry. Univ Massachusetts, Dept Chem, One Univ Ave, Lowell, MA 01854 USA.;Linnaeus Univ, Dept Chem & Biomed Sci, SE-39182 Kalmar, Sweden..
    QCM sensing of multivalent interactions between lectins and well-defined glycosylated nanoplatforms2019In: Biosensors & bioelectronics, ISSN 0956-5663, E-ISSN 1873-4235, Vol. 139, article id 111328Article in journal (Refereed)
    Abstract [en]

    Quartz crystal microbalance (QCM) methodology has been adopted to unravel important factors contributing to the "cluster glycoside effect" observed in carbohydrate-lectin interactions. Well-defined, glycosylated nanostructures of precise sizes, geometries and functionalization patterns were designed and synthesized, and applied to analysis of the interaction kinetics and thermodynamics with immobilized lectins. The nanostructures were based on Borromean rings, dodecaamine cages, and fullerenes, each of which carrying a defined number of carbohydrate ligands at precise locations. The synthesis of the Borromeates and dodecaamine cages was easily adjustable due to the modular assembly of the structures, resulting in variations in presentation mode. The binding properties of the glycosylated nanoplatforms were evaluated using flow-through QCM technology, as well as hemagglutination inhibition assays, and compared with dodecaglycosylated fullerenes and a monovalent reference. With the QCM setup, the association and dissociation rate constants and the associated equilibrium constants of the interactions could be estimated, and the results used to delineate the multivalency effects of the lectin-nanostructure interactions.

  • 2.
    Deng, Lingquan
    et al.
    KTH, School of Chemical Science and Engineering (CHE).
    Norberg, Oscar
    KTH, School of Chemical Science and Engineering (CHE).
    Uppalapati, Suji
    Portland State Univ, Dept Chem, Portland, OR 97201 USA..
    Yan, Mingdi
    Portland State Univ, Dept Chem, Portland, OR 97201 USA..
    Ramström, Olof
    KTH, School of Chemical Science and Engineering (CHE).
    CARB 102-Synthesis of novel photoreactive PFPA-carbohydrates for study of carbohydrate-protein interactions2009In: Abstract of Papers of the American Chemical Society, ISSN 0065-7727, Vol. 238Article in journal (Other academic)
  • 3.
    Dong, H
    et al.
    KTH, Superseded Departments (pre-2005), Chemistry.
    Pei, Z C
    KTH, Superseded Departments (pre-2005), Chemistry.
    Ramström, Olof
    KTH, Superseded Departments (pre-2005), Chemistry.
    Ester activation in nitrite-mediated carbohydrate epimerization2005In: Abstract of Papers of the American Chemical Society, ISSN 0065-7727, Vol. 230, p. U683-U683Article in journal (Other academic)
  • 4.
    Kong, Na
    et al.
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry.
    Shimpi, Manishkumar R.
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry.
    Park, Jaehyeung
    Univ Massachusetts, Dept Chem, Lowell, MA 01854 USA..
    Ramström, Olof
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Organic chemistry.
    Yan, Mingdi
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry.
    Carbohydrate conjugation through microwave-assisted functionalization of single-walled carbon nanotubes using perfluorophenyl azides (vol 405, pg 33, 2015)2015In: Carbohydrate Research, ISSN 0008-6215, E-ISSN 1873-426X, Vol. 412, p. 80-80Article in journal (Refereed)
  • 5.
    Kravchenko, Oleksandr
    et al.
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry.
    Timmer, Brian
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry.
    Biedermann, Maurice
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry.
    Inge, Ken
    Stockholm Univ, Dept Mat & Environm Chem, Stockholm, Sweden..
    Ramström, Olof
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Organic chemistry. Univ Massachusetts, Dept Chem, Lowell, MA USA..
    Stable CAAC-based complexes in dynamic olefin metathesis2018In: Abstract of Papers of the American Chemical Society, ISSN 0065-7727, Vol. 256Article in journal (Other academic)
  • 6.
    Larsson, Rikard
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry.
    Angelin, Marcus
    KTH, School of Chemical Science and Engineering (CHE), Chemistry.
    Vongvilai, Pornrapee
    KTH, School of Chemical Science and Engineering (CHE), Chemistry.
    Ramström, Olof
    KTH, School of Chemical Science and Engineering (CHE), Chemistry.
    ORGN 231-Dynamic catalytic screening of hydrolase substrates from adaptive combinatorial thiolester libraries2006In: Abstract of Papers of the American Chemical Society, ISSN 0065-7727, Vol. 232Article in journal (Other academic)
  • 7.
    Norberg, Oscar
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry.
    Wu, Bin
    Thota, Niranjan
    KTH, School of Chemical Science and Engineering (CHE), Chemistry.
    Ge, Jian-Tao
    Fauquet, Germain
    KTH, School of Chemical Science and Engineering (CHE), Chemistry.
    Saur, Ann-Kathrin
    Aastrup, Teodor
    Dong, Hai
    Yan, Mingdi
    KTH, School of Chemical Science and Engineering (CHE), Chemistry. Department of Chemistry, University of Massachusetts Lowell, 1 University Ave., MA, 01854 Lowell, USA.
    Ramström, Olof
    KTH, School of Chemical Science and Engineering (CHE), Chemistry. Department of Chemistry, University of Massachusetts Lowell, 1 University Ave., MA, 01854 Lowell, USA.
    Synthesis and binding affinity analysis of alpha 1-2-and alpha 1-6-O/S-linked dimannosides for the elucidation of sulfur in glycosidic bonds using quartz crystal microbalance sensors2017In: Carbohydrate Research, ISSN 0008-6215, E-ISSN 1873-426X, Vol. 452, p. 35-42Article, review/survey (Refereed)
    Abstract [en]

    The role of sulfur in glycosidic bonds has been evaluated using quartz crystal microbalance methodology. Synthetic routes towards alpha 1-2- and alpha 1-6-linked dimannosides with S-or O-glycosidic bonds have been developed, and the recognition properties assessed in competition binding assays with the cognate lectin concanavalin A. Mannose-presenting QCM sensors were produced using photoinitiated, nitrenemediated immobilization methods, and the subsequent binding study was performed in an automated flow-through instrumentation, and correlated with data from isothermal titration calorimetry. The recorded Kd-values corresponded well with reported binding affinities for the O-linked dimannosides with affinities for the alpha 1-2-linked dimannosides in the lower micromolar range. The S-linked analogs showed slightly disparate effects, where the alpha 1-6-linked analog showed weaker affinity than the O-linked dimannoside, as well as positive apparent cooperativity, whereas the alpha 1-2-analog displayed very similar binding compared to the O-linked structure. 

  • 8. Pei, Z
    et al.
    Larsson, R
    Aastrup, T
    Anderson, H
    Ramström, Olof
    KTH, Superseded Departments (pre-2005), Chemistry.
    Rapid screening of glycosyldisulfide lectin inhibitors from a dynamic combinatorial library2005In: Abstract of Papers of the American Chemical Society, ISSN 0065-7727, Vol. 230, p. U690-U690Article in journal (Other academic)
  • 9.
    Ramström, Olof
    KTH, Superseded Departments (pre-2005), Chemistry.
    Dynamic catalytic library generation and screening.2005In: Abstract of Papers of the American Chemical Society, ISSN 0065-7727, Vol. 229, p. U329-U329Article in journal (Other academic)
  • 10.
    Ramström, Olof
    et al.
    KTH, Superseded Departments (pre-2005), Chemistry.
    Pei, Z C
    KTH, Superseded Departments (pre-2005), Chemistry.
    Larsson, R
    KTH, Superseded Departments (pre-2005), Chemistry.
    Hermansson, M
    KTH, Superseded Departments (pre-2005), Chemistry.
    Generation and screening of dynamic combinatorial libraries.2004In: Abstract of Papers of the American Chemical Society, ISSN 0065-7727, Vol. 227, p. U158-U159Article in journal (Other academic)
  • 11.
    REN, Yansong
    et al.
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Organic chemistry.
    Hu, Lei
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Organic chemistry.
    Ramström, Olof
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Organic chemistry.
    Multienzymatic Cascade Synthesis of an Enantiopure (2R,5R)-1,3-Oxathiolane Anti-HIV Agent PrecursorManuscript (preprint) (Other academic)
    Abstract [en]

    An enantiopure (2R,5R)-1,3-oxathiolane derivative was obtained using amultienzymatic cascade protocol. By employing a combination of surfactant-treatedsubtilisin Carlsberg and Candida antarctica lipase B, the absolute configuration of theresulting 1,3-oxathiolane ring was efficiently controlled, resulting in an excellentenantiomeric excess (> 99%). This enantiopure 1,3-oxathiolane derivative is a keyprecursor to anti-HIV agents, such as lamivudine, through subsequent N-glycosylation.

  • 12.
    Ren, Yansong
    et al.
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Organic chemistry.
    Hu, Lei
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Organic chemistry.
    Ramström, Olof
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Organic chemistry.
    Multienzymatic cascade synthesis of an enantiopure (2R,5R)-1,3-oxathiolane anti-HIV agent precursor2019In: Molecular Catalysis, ISSN 2468-8231, Vol. 468, p. 52-56Article in journal (Refereed)
    Abstract [en]

    An enantiopure (2R,5R)-1,3-oxathiolane was obtained using a multienzymatic cascade protocol. By employing a combination of surfactant-treated subtilisin Carlsberg and Candida antarctica lipase B, the absolute configuration of the resulting 1,3-oxathiolane ring was efficiently controlled, resulting in an excellent enantiomeric excess (>99%). This enantiopure 1,3-oxathiolane derivative is a key precursor to anti-HIV agents, such as lamivudine, through subsequent N-glycosylation.

  • 13.
    REN, Yansong
    et al.
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Organic chemistry. KTH, Dept Chem Organ Chem, Stockholm, Sweden..
    Hu, Lei
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Organic chemistry. KTH, Dept Chem Organ Chem, Stockholm, Sweden..
    Ramström, Olof
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Organic chemistry. KTH, Dept Chem Organ Chem, Stockholm, Sweden..
    Multienzymatic, one-pot cascade synthesis of enantiopure lamivudine precursor (2R, 5R)-1,3-oxathiolane2016In: Abstract of Papers of the American Chemical Society, ISSN 0065-7727, Vol. 252Article in journal (Other academic)
  • 14.
    REN, Yansong
    et al.
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Organic chemistry.
    Kravchenko, Oleksandr
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Organic chemistry.
    Ramström, Olof
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Organic chemistry.
    Configurational and Constitutional Dynamics in Enamine Molecular SwitchesManuscript (preprint) (Other academic)
    Abstract [en]

    Dual configurational and constitutional dynamics in systems based on enamine molecularswitches has been systematically studied. pH-responsive moieties, such as 2-pyridyl and 2-quinolinyl units, were required on the “stator” part, also providing enamine stability throughintramolecular hydrogen-bonding (IMHB) effects. Upon protonation or deprotonation, forward andbackward switching could be rapidly achieved. Extension of the stator π-system in the 2-quinolinylderivative provided a higher E-isomeric equilibrium ratio under neutral conditions, pointing to ameans to achieve quantitative forward/backward isomerization processes. The ‘rotor’ part of theenamine switches exhibited constitutional exchange ability with primary amines. Interestingly,considerably higher exchange rates were observed with amines containing ester groups, indicatingpotential stabilization of the transition state trough IMHB. Acids, particularly BiIII, were found toefficiently catalyze the constitutional dynamic processes. In contrast, the enamine and the formeddynamic enamine system showed excellent stability under basic conditions. This coupledconfigurational and constitutional dynamics expand the scope of dynamic C-C and C-N bonds, andpotentiates further studies and applications in the fields of molecular machinery and systemschemistry.

  • 15.
    REN, Yansong
    et al.
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Organic chemistry.
    Kravchenko, Oleksandr
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Organic chemistry.
    Xie, Sheng
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Organic chemistry.
    Grape, Erik
    Inge, A. Ken
    Ramström, Olof
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Organic chemistry.
    Stimuli-responsive Enaminitrile Molecular Switches as Tunable AIEgens Covering theChromaticity Space and Acting as Vapor SensorsManuscript (preprint) (Other academic)
    Abstract [en]

    A family of responsive enaminitrile molecular switches showing tunable turn-onfluorescence upon switching and aggregation is reported. Activated by addition of acid/base,isomerization around the C=C bond could be effectuated, resulting in complete, reversible switchingto the E- or Z-isomers. Typical aggregation-induced emission could be recorded for one specificstate of the different switches. By subtle tailoring of the parent structure, a series of compounds withemission covering almost the full visible color range were obtained. The switchable AIE features ofthe enaminitrile structures enabled their demonstration as solid state chemosensors to detect acidicand basic vapors, where the emission displayed an “off-on-off” effect. X-ray crystal analysis andDFT calculations suggested a restriction of intramolecular rotation mechanism, and anintramolecular charge transfer effect in the AIE luminogens.

  • 16.
    Ren, Yansong
    et al.
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry.
    Svensson, Per H.
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry. RISE Biosci & Mat, Res Inst Sweden, Forskargatan 18, S-15136 Sodertalje, Sweden..
    Ramström, Olof
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry. Department of Chemistry, University of Massachusetts Lowell, 1 University Avenue, Lowell, MA, United States.
    A Multicontrolled Enamine Configurational Switch Undergoing Dynamic Constitutional Exchange2018In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 57, no 21, p. 6256-6260Article in journal (Refereed)
    Abstract [en]

    A multiresponsive enamine-based molecular switch is presented, in which forward/backward configurational rotation around the C=C bond could be precisely controlled by the addition of an acid/base or metal ions. Fluorescence turn-on/off effects and large Stokes shifts were observed while regulating the switching process with Cu-II. The enamine functionality furthermore enabled double dynamic regimes, in which configurational switching could operate in conjunction with constitutional enamine exchange of the rotor part. This behavior was used to construct a prototypical dynamic covalent switch system through enamine exchange with primary amines. The dynamic exchange process could be readily turned on/off by regulating the switch status with pH.

  • 17.
    Ren, Yansong
    et al.
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Organic chemistry. KTH - Royal Institute of Technology.
    Xie, Sheng
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Organic chemistry.
    Grape, Erik
    Inge, A. Ken
    Ramström, Olof
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Organic chemistry.
    Multistimuli-Responsive Enaminitrile Molecular Switches DisplayingH+‑Induced Aggregate Emission, Metal Ion-Induced Turn-OnFluorescence, and Organogelation Properties2018In: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 140, no 42, p. 13640-13643Article in journal (Refereed)
    Abstract [en]

    Multistimuli-responsive enaminitrile-based configurational switches displaying aggregation-induced emission (AIE), fluorescence turn-on effects, and supergelation properties are presented. The E-isomers dominated (>97%) in neutral/basic solution, and the structures underwent precisely controlled switching around the enamine C═C bond upon addition of acid/base. Specific fluorescence output was observed in response to different external input in the solution and solid states. In response to H+, configurational switching resulted in complete formation of the nonemissive Z-H+-isomers in solution, however displaying deep-blue to blue fluorescence (ΦF up to 0.41) in the solid state. In response to CuII in the solution state, the E-isomers exhibited intense, turn-on, blue-green fluorescence, which could be turned off by addition of competitive coordination. The acid/base-activated switching, together with the induced AIE-effects, further enabled the accomplishment of a responsive superorganogelator. In nonpolar solvents, a blue-fluorescent supramolecular gel was formed upon addition of acid to the E-isomer suspension. The gelation could be reversed by addition of base, and the overall, reversible process could be repeated at least five cycles.

  • 18.
    Schaufelberger, Fredrik
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry.
    Ramström, Olof
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Kinetic Self-Sorting of Dynamic Covalent Catalysts with Systemic Feedback Regulation2016In: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 138, no 25, p. 7836-7839Article in journal (Refereed)
    Abstract [en]

    Constructing small molecule systems that mimic the functionality exhibited in biological reaction networks is a key objective of systems chemistry. Herein, we report the development of a dynamic catalytic system where the catalyst activity is modulated through a dynamic covalent bond. By connecting a thermodynamically controlled rearrangement process to resolution under kinetic control, the catalyst system underwent kinetic self sorting, resulting in amplification of a more reactive catalyst while establishing a catalytic feedback mechanism. The dynamic catalyst system furthermore responded to catalytic events by self-perturbation to regulate its own activity, which in the case of upregulation gave rise to systemic autocatalytic behavior.

  • 19.
    Schaufelberger, Fredrik
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Ramström, Olof
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Programmed Error-Correction within Dynamic Catalyst Systems for the Morita-Baylis-Hillman reactionManuscript (preprint) (Other academic)
    Abstract [en]

    The understanding of complex reaction networks of small molecules with emergent systemic functionality is integral to both systems chemistry and origin-of-life studies. In this work, a dynamic catalytic system of nucleophilic catalysts for the Morita-Baylis-Hillman (MBH) reaction is demonstrated, exhibiting self-resolution behavior along with thermodynamically driven error-correction. A class of readily reversible MBH adducts from substrates with internal H-transfer capabilities is furthermore presented, displaying rate accelerations of retro-MBH reactions up to 10 000 times. The retro-MBH reaction was used as a design element in a self-resolving dynamic catalytic system, yielding a transient product that was eventually transformed into a more stable thermodynamic product. This study demonstrates efficient self-sorting of complex small molecular catalytic systems.

  • 20.
    Schaufelberger, Fredrik
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Seigel, Karolina
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Ramström, Olof
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Biomimetic Hydrogen Bonding Catalysis of Imine Exchange for Rapid Equilibration of Dynamic SystemsManuscript (preprint) (Other academic)
    Abstract [en]

    The reversibility of imine bonds has been exploited to great effect in the field of dynamic covalent chemistry, for example in the preparation of dynamic systems for a wide variety of applications. However, acid catalysis is commonly needed for efficient equilibration of imine mixtures. Herein, it is demonstrated that hydrogen bond donors, such as thioureas and squaramides, can catalyze the equilibration of dynamic imine systems under unprecedentedly mild conditions. Catalysis occurs in a range of solvents and in the presence of many sensitive additives, showing moderate to good rate accelerations for both imine metathesis and transimination with amines, hydrazines and hydroxylamines. Furthermore, the catalyst proved simple to immobilize, introducing both reusability and extended control of the equilibration process.

  • 21.
    Schaufelberger, Fredrik
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Timmer, Brian J. J.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Ramström, Olof
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Resolving a Reactive Organometallic Intermediate from Dynamic Directing Group Systems by Selective C-H ActivationManuscript (preprint) (Other academic)
    Abstract [en]

    Catalyst discovery from systems of potential precursors is a challenging endeavor. Herein, a new strategy applying dynamic chemistry to the identification of catalyst precursors from C-H activation of imines is proposed and evaluated. Using hydroacylation of imines as a model reaction, the selection of an organometallic reactive intermediate from a dynamic imine system, involving many potential directing group/metal entities, is demonstrated. The identity of the amplified reaction intermediate with the best directing group could be resolved in situ via ESI-MS, and coupling of the procedure to an iterative deconvolution protocol generated a system with high screening efficiency.

  • 22.
    Schaufelberger, Fredrik
    et al.
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry.
    Timmer, Brian J. J.
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry.
    Ramström, Olof
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry.
    Resolving a Reactive Organometallic Intermediate from Dynamic Directing Group Systems by Selective C-H Activation2018In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 24, no 1, p. 101-104Article in journal (Refereed)
    Abstract [en]

    Catalyst discovery from systems of potential precursors is a challenging endeavor. Herein, a new strategy applying dynamic chemistry to the identification of catalyst precursors from C-H activation of imines is proposed and evaluated. Using hydroacylation of imines as a model reaction, the selection of an organometallic reactive intermediate from a dynamic imine system, involving many potential directing group/metal entities, is demonstrated. The identity of the amplified reaction intermediate with the best directing group could be resolved in situ by ESI-MS, and coupling of the procedure to an iterative deconvolution protocol generated a system with high screening efficiency.

  • 23.
    Sundhoro, Madanodaya
    et al.
    Univ Massachusetts Lowell, Chem, Lowell, MA USA..
    Jeon, Seaho
    Univ Massachusetts Lowell, Chem, Lowell, MA USA..
    Hao, Nanjing
    Univ Massachusetts Lowell, Dept Chem, Lowell, MA USA..
    Park, Jaehyeung
    Univ Massachusetts Lowell, Dept Chem, Lowell, MA USA..
    Fischer, Andreas
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Inorganic Chemistry (closed 20110630).
    Ramström, Olof
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Organic chemistry. Royal Inst Technol, Dept Chem, Stockholm, Sweden..
    Yan, Mingdi
    Univ Massachusetts Lowell, Dept Chem, Lowell, MA USA..
    Perfluorophenyl azide-mediated Staudinger reaction and application in probing cell surface glycans2015In: Abstract of Papers of the American Chemical Society, ISSN 0065-7727, Vol. 250Article in journal (Other academic)
  • 24. Sundhoro, Madanodaya
    et al.
    Jeon, Seaho
    Park, Jaehyeung
    Ramström, Olof
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry. Univ Massachusetts Lowell, USA.
    Yan, Mingdi
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry. Univ Massachusetts Lowell, USA.
    Perfluoroaryl Azide Staudinger Reaction: A Fast and Bioorthogonal Reaction2017In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 56, no 40, p. 12117-12121Article in journal (Refereed)
    Abstract [en]

    We report a fast Staudinger reaction between perfluoroaryl azides (PFAAs) and aryl phosphines, which occurs readily under ambient conditions. A rate constant as high as 18m(-1)s(-1) was obtained between methyl 4-azido-2,3,5,6-tetrafluorobenzoate and methyl 2-(diphenylphosphanyl)benzoate in CD3CN/D2O. Furthermore, the iminophosphorane product was stable toward hydrolysis and aza-phosphonium ylide reactions. This PFAA Staudinger reaction proved to be an excellent bioothorgonal reaction. PFAA-derivatized mannosamine and galactosamine were successfully transformed into cell-surface glycans and efficiently labeled with phosphine-derivatized fluorophore-conjugated bovine serum albumin.

  • 25.
    Timmer, Brian
    et al.
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Organic chemistry.
    Schaufelberger, Fredrik
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Organic chemistry.
    Hammarberg, Daniel
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Organic chemistry.
    Franzen, Johan.
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Organic chemistry.
    Ramström, Olof
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Organic chemistry.
    Dinér, Peter
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Organic chemistry.
    Simple and Effective Integration of Green Chemistry and Sustainability Education into an Existing Organic Chemistry Course2018In: Journal of Chemical Education, ISSN 0021-9584, E-ISSN 1938-1328, Vol. 95, no 8, p. 1301-1306Article in journal (Refereed)
    Abstract [en]

    Green chemistry and sustainable development have become increasingly important topics for the education of future chemists. The cross-disciplinary nature of green chemistry and sustainable development often means these subjects are taught in conjunction with other subjects, such as organic chemistry and chemical engineering. Herein, a straightforward and efficient approach for vertical integration of green chemistry concepts within existing undergraduate organic chemistry courses is shown. The gradual self-evaluation, "greenification", and reassessment of an organic chemistry course at KTH Royal Institute of Technology from 2013 to 2017 is described, with particular focus on the laboratory course and a novel green chemistry project designed to promote sustainability thinking and reasoning. The laboratory project, which can also be conducted as an independent organic chemistry laboratory exercise, required students to critically evaluate variations of the same Pechmann condensation experiment according to the twelve principles of green chemistry. The course evaluation shows that, after the modifications, students feel more comfortable with the topics "green chemistry" and "sustainability" and consider these topics more important for their future careers. Furthermore, the ability of students to discuss and critically evaluate green chemistry parameters improved considerably as determined from the laboratory project reports.

  • 26.
    Vongvilai, Pornrapee
    et al.
    KTH, School of Chemical Science and Engineering (CHE).
    Angelin, Marcus
    KTH, School of Chemical Science and Engineering (CHE).
    Larsson, Rikard
    KTH, School of Chemical Science and Engineering (CHE), Chemistry.
    Ramström, Olof
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Organic chemistry.
    Dynamic combinatorial resolution: Direct substrate identification in asymmetric lipase-mediated transacylations.2009In: Abstract of Papers of the American Chemical Society, ISSN 0065-7727, Vol. 238Article in journal (Other academic)
  • 27.
    Xie, Sheng
    et al.
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Organic chemistry. College of Chemistry and Chemical Engineering, Hunan University, Changsha, 410082, China.
    Manuguri, Sesha
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry.
    Ramström, Olof
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Organic chemistry. University of Massachusetts Lowell, 1 University Ave., Lowell, MA 01854, United States.
    Yan, Mingdi
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Organic chemistry. University of Massachusetts Lowell, 1 University Ave., Lowell, MA 01854, United States.
    Impact of Hydrogen Bonding on the Fluorescence of N-Amidinated Fluoroquinolone2019In: Chemistry - An Asian Journal, ISSN 1861-4728, E-ISSN 1861-471X, Vol. 14, no 6, p. 910-916Article in journal (Refereed)
    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.

  • 28.
    Xie, Sheng
    et al.
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Organic chemistry.
    Zhou, Juan
    Chen, Xuan
    Univ Massachusetts Lowell, Dept Chem, Lowell, MA 01854 USA..
    Kong, Na
    Fan, Yanmiao
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Organic chemistry.
    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, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Organic chemistry.
    Yan, Mingdi
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Organic chemistry.
    A versatile catalyst-free perfluoroaryl azide-aldehyde-amine conjugation reaction2019In: MATERIALS CHEMISTRY FRONTIERS, ISSN 2052-1537, Vol. 3, no 2, p. 251-256Article in journal (Refereed)
    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.

  • 29.
    Zhang, Yang
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemical Engineering and Technology, Energy Processes.
    Xie, Sheng
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Yan, Mingdi
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Ramström, Olof
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Dynamic Covalent Chemistry of Aldehyde Enamines: Bi-III- and Sc-III-Catalysis of Amine-Enamine Exchange2017In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 23, no 49, p. 11908-11912Article in journal (Refereed)
    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.

  • 30.
    Zhang, Yang
    et al.
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemical Engineering, Energy Processes.
    Xie, Sheng
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Organic chemistry.
    Yan, Mingdi
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Organic chemistry.
    Ramström, Olof
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Organic chemistry.
    Enzyme- and ruthenium-catalyzed dynamic kinetic resolution involving cascade alkoxycarbonylations for asymmetric synthesis of 5-Substituted N-Aryloxazolidinones2019In: Molecular Catalysis, ISSN 2468-8231, Vol. 470, p. 138-144Article in journal (Refereed)
    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.

1 - 30 of 30
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