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Stereocontrolled 1-S-glycosylation and comparative binding studies of photoprobe-thiosaccharide conjugates with their O-linked analogs
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
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2013 (English)In: Pure and Applied Chemistry, ISSN 0033-4545, E-ISSN 1365-3075, Vol. 85, no 9, 1789-1801 p.Article in journal (Refereed) Published
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.

Place, publisher, year, edition, pages
2013. Vol. 85, no 9, 1789-1801 p.
Keyword [en]
carbohydrates, photochemistry, protein interactions, organic materials, organic synthesis, stereocontrol
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:kth:diva-41972DOI: 10.1351/PAC-CON-12-08-13ISI: 000323700200004Scopus ID: 2-s2.0-84883377211OAI: oai:DiVA.org:kth-41972DiVA: diva2:445626
Funder
Swedish Research Council, 622-2003-2343
Note

QC 20130930. Updated from submitted to published.

Available from: 2011-10-04 Created: 2011-10-04 Last updated: 2017-12-08Bibliographically approved
In thesis
1. Photochemical Surface Functionalization: Synthesis, Nanochemistry and Glycobiological Studies
Open this publication in new window or tab >>Photochemical Surface Functionalization: Synthesis, Nanochemistry and Glycobiological Studies
2011 (English)Doctoral thesis, comprehensive summary (Other academic)
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.

Place, publisher, year, edition, pages
Stockholm: KTH Royal Institute of Technology, 2011. 86 p.
Series
Trita-CHE-Report, ISSN 1654-1081 ; 2011:47
Keyword
Carbohydrates, Glycobiology, Carbohydrate-protein interactions, Perfluorophenylazide (PFPA), Photochemistry, Carbohydrate surface immobilization, Carbohydrate microarrays, Surface plasmon resonance (SPR), Quartz crystal microbalance (QCM), Atomic force microscopy (AFM), Glyconanomaterials, Concanavalin A (Con A), Cyanovirin-N (CV-N), 1-Glycosyl thiols; Mutarotation, 1-S-glycosylation, Stereocontrol
National Category
Organic Chemistry
Identifiers
urn:nbn:se:kth:diva-41973 (URN)978-91-7501-072-4 (ISBN)
Public defence
2011-10-21, F3, Lindstedtsvägen 26, KTH, Stockholm, 13:00 (English)
Opponent
Supervisors
Note
QC 20111004Available from: 2011-10-04 Created: 2011-10-04 Last updated: 2011-10-04Bibliographically approved
2. Photochemical Ligation Techniques for Carbohydrate Biosensors and Protein Interaction Studies
Open this publication in new window or tab >>Photochemical Ligation Techniques for Carbohydrate Biosensors and Protein Interaction Studies
2012 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

This thesis concerns the development of surface ligation techniques for the preparation of carbohydrate biosensors. Several methodologies were developed based on efficient photochemical insertion reactions which quickly functionalize polymeric materials, with either carbohydrates or functional groups such as alkynes or alkenes. The alkyne/alkene surfaces were then treated with carbohydrate azides or thiols and reacted under chemoselective Cu-catalyzed azide-alkyne cycloaddition (CuAAC) or photo-radical thiol-ene/yne click chemistry, thus creating a range of carbohydrate biosensor surfaces under ambient conditions. The methodologies were evaluated by quartz crystal microbalance (QCM) and surface plasmon resonance (SPR) flow through instrumentations with recurring injections of a range of lectins, allowing for real-time analysis of the surface interactions. The developed methods were proven robust and versatile, and the generated carbohydrate biosensors showed high specificities and good capacities for lectin binding.  The methods were then used to investigate how varying the glycan linker length and/or a sulfur-linkage affect the subsequent protein binding. The survey was further explored by investigating the impact of sulfur in glycosidic linkages on protein binding, through competition assays with various O/S-linked disaccharides in solution interactions with lectins.

Place, publisher, year, edition, pages
Stockholm: KTH Royal Institute of Technology, 2012. xi, 89 p.
Series
Trita-CHE-Report, ISSN 1654-1081 ; 2012:10
Keyword
Carbohydrates, Biosensors, CuAAC, Photochemistry, Thiol-ene/yne, Perfluorophenylazide (PFPA), Lectins, Molecular recognition, Quartz crystal microbalance (QCM), Surface plasmon resonance (SPR)
National Category
Organic Chemistry
Identifiers
urn:nbn:se:kth:diva-90956 (URN)978-91-7501-271-1 (ISBN)
Public defence
2012-03-30, F3, Lindstedtsvägen 26, Stockholm, 10:00 (English)
Opponent
Supervisors
Note
QC 20120309Available from: 2012-03-09 Created: 2012-03-05 Last updated: 2012-03-09Bibliographically approved

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