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  • 1.
    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.

  • 2.
    Deng, Lingquan
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Photochemical Surface Functionalization: Synthesis, Nanochemistry and Glycobiological Studies2011Doktoravhandling, med artikler (Annet vitenskapelig)
    Abstract [en]

    This thesis mainly deals with the development of photochemical approaches to immobilize carbohydrates on surfaces for glycobiological studies. These approaches have been incorporated into a number of state-of-the-art nanobio-platforms, including carbohydrate microarrays, surface plasmon resonance (SPR), quartz crystal microbalance (QCM), atomic force microscopy (AFM), and glyconanomaterials. All the surfaces have displayed good binding capabilities and selectivities after functionalization with carbohydrates, and a range of important data have been obtained concerning surface characteristics and carbohydrate-protein interactions, based on the platforms established. Besides, a variety of non-carbohydrate and carbohydrate-based molecules have been synthesized, during which process the mutarotation of 1-glycosyl thiols and the stereocontrol in 1-S-glycosylation reactions have been thoroughly studied.

  • 3.
    Deng, Lingquan
    et al.
    KTH, Skolan för kemivetenskap (CHE).
    Norberg, Oscar
    KTH, Skolan för kemivetenskap (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, Skolan för kemivetenskap (CHE).
    CARB 102-Synthesis of novel photoreactive PFPA-carbohydrates for study of carbohydrate-protein interactions2009Inngår i: Abstract of Papers of the American Chemical Society, ISSN 0065-7727, Vol. 238Artikkel i tidsskrift (Annet vitenskapelig)
  • 4.
    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.

  • 5.
    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.

  • 6.
    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)
  • 7.
    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.

  • 8. Madwar, Carolin
    et al.
    Kwan, William Chu
    Deng, Lingquan
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Schmidt, Rolf
    Zou, Shan
    Cuccia, Louis A.
    Perfluorophenyl Azide Immobilization Chemistry for Single Molecule Force Spectroscopy of the Concanavalin A/Mannose Interaction2010Inngår i: Langmuir, ISSN 0743-7463, E-ISSN 1520-5827, Vol. 26, nr 22, s. 16677-16680Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    The versatility of perfluorophenyl azide (PFPA) derivatives makes them useful for attaching a wide variety of biomoleculcs and polymers to surfaces. Herein, it single molecule force spectroscopy (SMFS) study of the concanavalin A/mannose interaction was carried out using PFPA immobilization chemistry. SMFS of the concanavalin A/mannose interaction yielded in average unbinding force of 70-80 pN for loading rates between 8000 and 40 000 pN/s for mannose surfaces on aminated glass. and an unbinding force of 57 +/- 20 pN at 6960 pN/s for mannose surfaces on gold-coated glass. Dynamic force spectroscopy was used to determine the dissociation rate constant, k(off), for this interaction to be 0.16 s(-1).

  • 9.
    Norberg, Oscar
    et al.
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Deng, Lingquan
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Aastrup, Teodor
    Yan, Mingdi
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Photo-Click Immobilization on Quartz Crystal Microbalance Sensors for Selective Carbohydrate-Protein Interaction Analyses2011Inngår i: Analytical Chemistry, ISSN 0003-2700, E-ISSN 1520-6882, Vol. 83, nr 3, s. 1000-1007Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    A photoclick method based on azide photoligation and Cu-catalyzed azide-alkyne cycloaddition has been evaluated for the immobilization of carbohydrates to polymeric materials. The biomolecular recognition properties of the materials have been investigated with regard to applicable polymeric substrates and selectivity of protein binding. The method was used to functionalize a range of polymeric surfaces (polystyrene, polyacrylamide, poly(ethylene glycol), poly(2-ethyl-2-oxazoline), and polypropene) with various carbohydrate structures (based on alpha-D-mannose, beta-D-galactose, and N-acetyl-beta-D-glucosamine). The functionalized surfaces were evaluated in real-time studies of protein-carbohydrate interactions using a quartz crystal microbalance flow through system with a series of different carbohydrate-binding proteins (lectins). The method proved to be robust and versatile, resulting in a range of efficient sensors showing high and predictable protein selectivities.

  • 10.
    Norberg, Oscar
    et al.
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Deng, Lingquan
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Yan, Mingdi
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Photo-Click Immobilization of Carbohydrates on Polymeric Surfaces - A Quick Method to Functionalize Surfaces for Biomolecular Recognition Studies2009Inngår i: Bioconjugate chemistry, ISSN 1043-1802, E-ISSN 1520-4812, Vol. 20, nr 12, s. 2364-2370Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    Methods to rapidly functionalize specific polymeric surfaces with alkynes, which can subsequently be linked to azide-containing carbohydrates, are presented. The methods comprise two main concepts: azide photoligation and Cu-catalyzed azide-alkyne cycloaddition. 2-Azidoethyl-functionalized CL-D-mannopyranoside was synthesized and covalently attached to alkyne-functionalized polymeric surfaces using the techniques. The protein recognition properties of the carbollydrate-presenting surfaces were evaluated using quartz crystal microbalance biosensor instrumentation.

  • 11. Tyagi, Anuradha
    et al.
    Wang, Xin
    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.
    Photogenerated carbohydrate microarrays to study carbohydrate-protein interactions using surface plasmon resonance imaging2010Inngår i: Biosensors & bioelectronics, ISSN 0956-5663, E-ISSN 1873-4235, Vol. 26, nr 2, s. 344-350Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    A photochemical strategy to generate carbohydrate microarrays on flat sensor surfaces, and to study the protein-binding effects of these arrays by surface plasmon resonance imaging is described. The approach was validated using a panel of carbohydrate-binding proteins. The coupling agents, thiol-functionalized perfluorophenyl azides, allow the covalent attachment of underivatized carbohydrates to gold surfaces by a fast photochemical reaction. Carbohydrate microarrays composed of 3,6-di-O-(alpha-D-mannopyranosyl)-D-mannopyranose (Man3), 2-O-alpha-D-mannopyranosyl-D-mannopyranose (Man2), D-mannose (Man), D-glucose (Glc), and D-galactose (Gal) were constructed, and the binding studies were carried out in real-time using surface plasmon resonance imaging. Results showed that the immobilized carbohydrate ligands retained their binding affinities with lectins, the rank order of which was consistent with that of the free ligands in solution. The detection limit of Man3, Man2, Man, and Glc with the lectin Concanavalin A was measured to be 0.29 nM, 0.18 nM, 0.61 nM, and 3.1 nM, respectively. In addition, soybean agglutinin and Griffonia simplicifolia lectin II were tested on the array, and the results were consistent with the binding selectivity of these lectins with the carbohydrate ligands.

  • 12. Wang, Xin
    et al.
    Matei, Elena
    Deng, Lingquan
    Koharudin, Leonardus
    Gronenborn, Angela M.
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Yan, Mingdi
    Sensing lectin-glycan interactions using lectin super-microarrays and glycans labeled with dye-doped silica nanoparticles2013Inngår i: Biosensors & bioelectronics, ISSN 0956-5663, E-ISSN 1873-4235, Vol. 47, s. 258-264Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    A new microarray platform, based on lectin super-microarrays and glycans labeled with dye-doped nanoparticles, has been developed to study glycan-lectin interactions. Glycan ligands were conjugated onto fluorescein-doped silica nanoparticles (FSNPs) using a general photocoupling chemistry to afford FSNP-labeled glycan probes. Lectins were printed on epoxy slides in duplicate sets to generate lectin super-microarrays where multiple assays could be carried out simultaneously in each lectin microarray. Thus, the lectin super-microarray was treated with FSNP-labeled glycans to screen for specific binding pairs. Furthermore, a series of ligand competition assays were carried out on a single lectin super-microarray to generate the dose-response curve for each glycan-lectin pair, from which the apparent affinity constants were obtained. Results showed 4-7 orders of magnitude increase in affinity over the free glycans with the corresponding lectins. Thus, the glycan epitope structures having weaker affinity than the parent glycans could be readily identified and analyzed from the lectin super-microarrays.

  • 13. 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).

  • 14.
    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.

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