通过改良的 Julia 烯烃化反应合成取代的外源性葡萄糖，并鉴定为选择性β-葡萄糖苷酶抑制剂。

Synthesis of substituted exo-glucals via a modified Julia olefination and identification as selective β-glucosidase inhibitors.

机构信息

Laboratoire Chimie Organique 2 Glycochimie, Université de Lyon, ICBMS, UMR 5246 - CNRS, Bat. 308 - Curien (CPE Lyon), Université Claude Bernard Lyon 1, 43 Bd. du 11 Novembre 1918, 69622 Villeurbanne, France.

出版信息

Org Biomol Chem. 2014 Jan 28;12(4):690-9. doi: 10.1039/c3ob41926f.

DOI:10.1039/c3ob41926f

PMID:24305697

Abstract

A series of fluorine and non-fluorine-substituted C-glucosylidenes (exo-glucals) has been synthesized via a modified Julia olefination. The deprotected exo-glucals were prepared in five steps from commercially available d-gluconolactone. The evaluation of this original family of compounds against a panel of glycosidases showed a highly specific in vitro activity towards mammalian β-glucosidase depending on the double bond substituents.

摘要

通过改良的 Julia 烯丙基化反应，合成了一系列氟代和非氟代 C-糖基烯丙基（外消旋葡糖醛酸）。通过商业可得的 d-葡萄糖酸内酯，经过五步反应得到脱保护的外消旋葡糖醛酸。对该系列化合物进行了一系列糖苷酶的体外活性评估，结果表明，根据双键取代基的不同，该化合物家族对哺乳动物β-葡萄糖苷酶具有高度的特异性。