Stereoselective synthesis of light-activatable perfluorophenylazide-conjugated carbohydrates for glycoarray fabrication and evaluation of structural effects on protein binding by SPR imaging
2011 (English)In: Organic and biomolecular chemistry, ISSN 1477-0520, E-ISSN 1477-0539, Vol. 9, no 9, 3188-3198 p.Article in journal (Refereed) Published
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.
Place, publisher, year, edition, pages
2011. Vol. 9, no 9, 3188-3198 p.
IdentifiersURN: urn:nbn:se:kth:diva-33214DOI: 10.1039/c1ob05040kISI: 000289488000018ScopusID: 2-s2.0-79954444517OAI: oai:DiVA.org:kth-33214DiVA: diva2:418405
FunderSwedish Research Council
QC 201105232011-05-232011-05-022012-03-09Bibliographically approved