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Oligomers of glycamino acid.

Abstract：

:Glycamino acids, a family of sugar amino acids, are derivatives of C-glycosides that possesses a carboxyl group at the C-1 position and an amino group replacing one of the hydroxyl groups at either the C-2, 3, 4, or 6 position. We have prepared a series of glucose-type glycamino acids as monomeric building blocks: these are derivatives of 2-NH(2)-Glc-beta-CO(2)H 1, 3-NH(2)-Glc-beta-CO(2)H 2, 4-NH(2)-Glc-beta-CO(2)H 3, and 6-NH(2)-Glc-beta-CO(2)H 4 and constructed four types of homo-oligomers, beta(1-->2)-linked I, beta(1-->3)-linked II, beta(1-->4)-linked III, and beta(1-->6)-linked IV, employing the well-established N-Boc and BOP strategy. CD and NMR spectral studies of these oligomers suggested that only the beta(1-->2)-linked homo-oligomer possessed a helical structure that seems to be predetermined by the linkage position. Homo-oligomers with beta(1-->2)-linkages I and beta(1-->6)-linkages IV were also subjected to O-sulfation, and these O-sulfated oligomers were found to be able, in a linkage-specific manner, to effectively inhibit L-selectin-mediated cell adhesion, HIV infection, and heparanase activity without the anticoagulant activity associated with naturally occurring sulfated polysaccharides such as heparin.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Suhara Y,Yamaguchi Y,Collins B,Schnaar RL,Yanagishita M,Hildreth JE,Shimada I,Ichikawa Y

doi

10.1016/s0968-0896(02)00020-2

subject

Has Abstract

pub_date

2002-06-01 00:00:00

pages

1999-2013

issue

6

eissn

0968-0896

issn

1464-3391

pii

S0968089602000202

journal_volume

10

pub_type

杂志文章

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