Synthesis and Binding Affinity Analysis of α1-2- and α1-6-O/S-linked Dimannosides for the Elucidation of Sulfur in Glycosidic Bonds using Quartz Crystal Microbalance Sensors
(English)Article in journal (Other academic) Submitted
Synthetic routes towards α1-2- and α1-6-linked dimannosides with S- or O-glycosidic bonds are presented. A glycosylation method was developed in which a sulfhydryl glycosyl acceptor was coupled to a 1-O-acetyl-glycosyl donor under Lewis acid catalysis. Final debenzylation of the S-linked dimannosides were accomplished through Birch reduction in high yields. The protein recognition properties of the synthesized dimannosides were then evaluated in a competition binding assay with the model lectin Con A, to investigate the effect of sulfur in the glycosidic bonds. Mannose-presenting surfaces were produced according to a previously reported Photo-Click immobilization method and the subsequent binding study was performed in an automated QCM flow through instrumentation. The recorded EC50-values correlated well to previously reported binding affinities for the O-linked dimannosides. Results were in agreement with known binding affinities, where the S-analogs displayed slightly weaker binding and a positive apparent cooperativity.
IdentifiersURN: urn:nbn:se:kth:diva-90848OAI: oai:DiVA.org:kth-90848DiVA: diva2:507541
QS 2012 QS 201203282012-03-052012-03-012012-03-28Bibliographically approved