氨基糖的N-烷基化对糖苷酶抑制特异性的影响。
Change in specificity of glycosidase inhibition by N-alkylation of amino sugars.
作者信息
al Daher S, Fleet G, Namgoong S K, Winchester B
机构信息
Department of Biochemistry, King's College London, U.K.
出版信息
Biochem J. 1989 Mar 1;258(2):613-5. doi: 10.1042/bj2580613.
Abstract
The synthetic amino sugar 1,4-dideoxy-1,4-imino-L-allitol (DIA) is a moderately good inhibitor of human liver alpha-D-mannosidases and a weak inhibitor of alpha-L-fucosidase, N-acetyl-beta-D-hexosaminidase and beta-D-mannosidase. Methylation of the ring nitrogen of DIA markedly decreases the inhibition of all the glycosidases except N-acetyl-beta-D-hexosaminidase. N-Benzylation of DIA essentially abolishes all inhibitory activity, except towards alpha-L-fucosidase, which is more strongly inhibited than by either DIA or N-methyl-DIA. This is the first report of a change of specificity of inhibition of a glycosidase inhibitor by substitution of the ring nitrogen.
摘要
合成氨基糖1,4-二脱氧-1,4-亚氨基-L-阿糖醇（DIA）是一种对人肝脏α-D-甘露糖苷酶抑制作用中等良好的抑制剂，对α-L-岩藻糖苷酶、N-乙酰-β-D-己糖胺酶和β-D-甘露糖苷酶的抑制作用较弱。DIA环氮甲基化显著降低了除N-乙酰-β-D-己糖胺酶外所有糖苷酶的抑制作用。DIA的N-苄基化基本消除了所有抑制活性，但对α-L-岩藻糖苷酶的抑制作用除外，α-L-岩藻糖苷酶受到的抑制比DIA或N-甲基-DIA更强。这是关于通过环氮取代改变糖苷酶抑制剂抑制特异性的首次报道。
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