A convenient and efficient synthesis of SLeX analogs

被引:40
作者
Hayashi, M
Tanaka, M
Itoh, M
Miyauchi, H
机构
[1] Research Center, Sumitomo Pharmaceuticals, Co., Ltd., Konohana-ku, Osaka 554, 1-98
关键词
D O I
10.1021/jo960125f
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Described is the preparation and use of tetrasaccharide 1, which enables a rapid and preparative scale synthesis of sialyl Lewis X (SLeX) analogs having 1-O- and 2-N-disubstituted glucosamine (GlcN) moieties. Such modifications should bring a dramatic change of the physical and pharmacological properties of the SLeX analogs. Therefore, tetrasaccharide 1 is a convenient intermediate for the synthesis of various SLeX analogs, since it has convertible 2-(trimethylsilyl)ethyl(SE) glycoside and the free amino group on GlcN moiety. The intermediate 1 was constructed from a glucosamine derivative by a highly efficient combined use of enzymatic galactosylation/sialylation and chemical fucosylation. Thus obtained 1 was converted into SLeX analogs by N-substitution followed by transformation of SE glycoside into other glycosides and deprotection. These synthesized analogs were found to inhibit cell adhesion of HL-60 cells to recombinant soluble human E-selectin.
引用
收藏
页码:2938 / 2945
页数:8
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