Synthesis of mannose-containing analogues of (1-->6)-branched (1-->3)-glucohexaose

Zicheng Wu; Fanzuo Kong

doi:10.1016/j.carres.2003.10.015

Synthesis of mannose-containing analogues of (1-->6)-branched (1-->3)-glucohexaose

Carbohydr Res. 2004 Jan 22;339(2):377-84. doi: 10.1016/j.carres.2003.10.015.

Authors

Zicheng Wu¹, Fanzuo Kong

Affiliation

¹ Research Center for Eco-Environmental Sciences, Academia Sinica, P.O. Box 2871, 100085, Beijing, China.

PMID: 14698896
DOI: 10.1016/j.carres.2003.10.015

Abstract

Coupling of the trisaccharide acceptor 2,4,6-tri-O-acetyl-beta-D-glucopyranosyl-(1-->3)-[2,3,4,6-tetra-O-benzoyl-beta-D-glucopyranosyl-(1-->6)]-5-O-acetyl-1,2-O-isopropylidene-alpha-D-glucofuranose (2) with the trisaccharide donor 2,3,4,6-tetra-O-benzoyl-alpha-D-annopyranosyl-(1-->3)-[2,3,4,6-tetra-O-benzoyl-beta-D-glucopyranosyl-(1-->6)]-2,4-di-O-acetyl-alpha-D-glucopyranosyl trichloroacetimidate (1) gave an alpha-linked hexasaccharide 3, while coupling of 2 with the trisaccharide donor 2,3,4,6-tetra-O-benzoyl-alpha-D-mannopyranosyl-(1-->3)-[2,3,4,6-tetra-O-benzoyl-alpha-D-mannopyranosyl-(1-->6)]-2,4-di-O-acetyl-alpha-D-glucopyranosyl trichloroacetimidate (7) produced alpha- 8 and beta-linked 12 hexasaccharides in a ratio of 3:2. Deprotection of 3, 8, and 12 afforded the analogues of the immunomodulator beta-D-Glcp-(1-->3)-[beta-D-Glcp-(1-->6)]-alpha-D-Glcp-(1-->3)-beta-D-Glcp-(1-->3)-[beta-D-Glcp-(1-->6)]-D-Glcp (A).

MeSH terms

Carbohydrate Conformation
Carbohydrate Sequence
Glucose / chemistry*
Mannose / chemistry*
Molecular Sequence Data
Molecular Structure
Oligosaccharides / chemical synthesis*
Oligosaccharides / chemistry*

Substances

Oligosaccharides
Glucose
Mannose