C-glycoside based mimics of D-myo-inositol 1,4,5-trisphosphate

被引：18

作者：

Rosenberg, HJ

Riley, AM

Correa, V

Taylor, CW

Potter, BVL

机构：

[1] Univ Bath, Wolfson Lab Med Chem, Dept Pharm & Pharmacol, Bath BA2 7AY, Avon, England

[2] Univ Cambridge, Dept Pharmacol, Cambridge CB2 1QJ, England

来源：

CARBOHYDRATE RESEARCH | 2000年 / 329卷 / 01期

基金：

英国惠康基金;

关键词：

adenophostin; myo-inositol; selective protection;

D O I：

10.1016/S0008-6215(00)00175-0

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：

Epimeric C-glycoside based polyphosphates, alpha- and beta-D-glucopyranosylmethanol 3,4,1'-trisphosphates (8 and 9) were prepared from D-glucose. The key intermediate, allyl 2,6-di-O-benzyl-alpha-D-glucopyranoside, was prepared in five steps (67% yield) from allyl alpha-D-glucopyranoside without the need for chromatography. Compounds 8 and 9 were shown to be full agonists at the Ins(1,4,5)P-3 receptors of permeabilised hepatocytes, but with markedly different potencies. Such C-glycoside analogues are worthy of further development as Ins(1,4,5)P-3 receptor ligands. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：7 / 16

页数：10

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