Synthesis and biological evaluation of a new sialyl Lewis X mimetic derived from lactose

被引：24

作者：

Chervin, SM

Lowe, JB

Koreeda, M ^{[1
]}

机构：

[1] Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA

[2] Univ Michigan, Dept Med Chem, Ann Arbor, MI 48109 USA

[3] Univ Michigan, Sch Med, Howard Hughes Med Inst, Ann Arbor, MI 48109 USA

[4] Univ Michigan, Sch Med, Dept Pathol, Ann Arbor, MI 48109 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2002年 / 67卷 / 16期

关键词：

D O I：

10.1021/jo025579t

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A sialyl Lewis X (sLe(x)) mimetic compound, 2-(trimethylsilyl)ethyl 3-O-carboxymethyl-beta-D-galactopyranosyl-(1-->4)-[alpha-L-fucosul-(1-->6)]beta-D-glucopyranoside (2a), lids been synthesized in 14 steps from D-lactose. This synthesis features the use of the activated glycosylating donor, lactosyl iodide, in a Koenigs-Knorr sequence, the regioselective derivatization at the C-3 position of the galactose moiety, and the stereoselective construction of a fucose-alpha(1-->6)-lactose linkage. The mimetic was tested for its ability to inhibit human polymorphonuclear leukocyte (hPMNL) adhesion to immobilized recombinant human E-selectin under shear stress conditions.

引用

页码：5654 / 5662

页数：9

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