[Synthesis of modified oligosaccharides of the N-glycoprotein as substrate for N-acetylglucosaminyltransferase I]

H Paulsen; F Reck; I Brockhausen

doi:10.1016/0008-6215(92)85006-l

[Synthesis of modified oligosaccharides of the N-glycoprotein as substrate for N-acetylglucosaminyltransferase I]

Carbohydr Res. 1992 Dec 15:236:39-71. doi: 10.1016/0008-6215(92)85006-l.

[Article in German]

Authors

H Paulsen¹, F Reck, I Brockhausen

Affiliation

¹ Institut für Organische Chemie, Universität Hamburg, Deutschland.

PMID: 1291062
DOI: 10.1016/0008-6215(92)85006-l

Abstract

In the synthesis of modified derivatives of octyl O-(alpha-D-mannopyranosyl)-(1-->3)-O-[(alpha-D-mannopyranosyl)-(1-->6)]- beta-D-mannopyranoside, 4.,5-epoxypentyl, a 4-diazirinopentyl, and a 5-(iodoacetamido)pentyl group were attached to the 3''-OH of the trisaccharide. The diazirino derivative may be especially suitable for photolabeling of the active site of N-acetylglucosaminyltransferase I (GlcNAcT-I). In addition, the 2'-OH group of the above-mentioned trisaccharide was reduced to a 2'-deoxy group and substituted 2'-O-methyl group.

Publication types

English Abstract
Research Support, Non-U.S. Gov't

MeSH terms

Binding Sites / physiology
Carbohydrate Sequence
Glycoproteins / chemistry*
Molecular Sequence Data
Molecular Structure
N-Acetylglucosaminyltransferases / metabolism*
Oligosaccharides / chemical synthesis*
Substrate Specificity

Substances

Glycoproteins
Oligosaccharides
N-Acetylglucosaminyltransferases
alpha-1,3-mannosyl-glycoprotein beta-1,2-N-acetylglucosaminyltransferase I