Stereocontrolled 1-S-glycosylation and comparative binding studies of photoprobe-thiosaccharide conjugates with their O-linked analogs
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
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.
carbohydrates, photochemistry, protein interactions, organic materials, organic synthesis, stereocontrol
IdentifiersURN: urn:nbn:se:kth:diva-41972DOI: 10.1351/PAC-CON-12-08-13ISI: 000323700200004ScopusID: 2-s2.0-84883377211OAI: oai:DiVA.org:kth-41972DiVA: diva2:445626
FunderSwedish Research Council, 622-2003-2343
QC 20130930. Updated from submitted to published.2011-10-042011-10-042013-09-30Bibliographically approved