Synthesis of ethyl 2-acetamido-6-S-(5-amino-5-deoxy-beta-D- arabinopyranosyl)-2-deoxy-1,6-dithio-beta-D-glucopyranoside: a sulfur-linked 5-amino-5-deoxyglycopyranosyl disaccharide.
A novel pseudo-disaccharide having an imino sugar residue at the non-reducing end, namely, a sulfur-linked 5-amino-5-deoxyglycopyranosyl disaccharide, which is a potential specific inhibitor for glycosidases that recognize not only the glycosidic linkage but also the aglycone moiety, was synthesized. Glycosidation of N-Boc-5-amino-5-deoxy-D-arabinose with ethyl 2-acetamido-3,4-di-O-acetyl-2-deoxy-1,6-dithio-beta-D- glucopyranoside in the presence of TsOH gave exclusively the corresponding 1,2-cis-linked thioglycoside. The interglycosidic linkage proved stable enough under conditions for the deprotection of the N-Boc group with TFA. This pseudodisaccharide was unstable at pH > 5, but stable at lower pH. The sulfur-linked 5-amino-5-deoxyglycopyranosyl disaccharide was shown to be formed from 5-amino-5-deoxy-D-arabinose and ethyl 2-acetamido-2-deoxy-1,6-dithio-beta-D-glucopyranoside in an acidic buffer solution.
Suzuki
K
K
Department of Life Science, Faculty of Bioscience and Biotechnology, Tokyo Institute of Technology, Yokohama, Japan.
Hashimoto
H
H
D004187:Disaccharides / Q000138:chemical synthesis*; D006863:Hydrogen-Ion Concentration; D008956:Models, Chemical; D013696:Temperature; D013863:Thioglucosides / Q000138:chemical synthesis*; D013865:Thioglycosides / Q000138:chemical synthesis*
D004187:Disaccharides; D013863:Thioglucosides; D013865:Thioglycosides; C410144:ethyl 2-acetamido-6-S-(5-amino-5-deoxyarabinopyranosyl)-2-deoxy-1,6-dithioglucopyranoside