Enzymatic synthesis of a sialyl Lewis X dimer from egg yolk as an inhibitor of E-selectin

被引：36
作者：
Lin, CH
Shimazaki, M
Wong, CH
Koketsu, M
Juneja, LR
Kim, M
机构：
[1] Scripps Res Inst, DEPT CHEM, LA JOLLA, CA 92037 USA
[2] TAIYO KAGAKU CO LTD, CENT RES LABS, YOKKAICHI, MIE 510, JAPAN
来源：
BIOORGANIC & MEDICINAL CHEMISTRY | 1995年 / 3卷 / 12期
关键词：
D O I：
10.1016/0968-0896(95)00150-6
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
A dimeric sialyl Lewis X (SLe(x)) glycopeptide was synthesized enzymatically in three steps from an N-linked oligosaccharide prepared from egg yolk. Treatment of delipidated hen egg yolk with the protease Orientase and neuraminidase gave a dimeric N-acetyllactosamine-containing oligosaccharide linked to asparagine. Addition of sialic acid and fucose catalyzed by alpha-2,3-sialyltransferase and alpha-1,3-fucosyltransferase provided the dimeric SLe(x), which was shown to be as active as monomeric SLe(x) as an inhibitor of E-selectin with IC50 0.75 mM. The synthetic dimeric SLe(x) of the mucin type (i.e. SLe(x) linked to the 3- and 6-OH groups of Gal) is, however, about five times as active as the monomer. It is suggested that dimeric SLe(x) glycopeptides of the mucin type would be effective ligands for E-selectin.
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页码：1625 / 1630
页数：6
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