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胆甾醇-6-O-十四烷酰基-α-D-吡喃葡萄糖苷的酶促化学合成:幽门螺杆菌促进的宿主胆固醇流出的产物。

Chemoenzymatic synthesis of cholesteryl-6-O-tetradecanoyl-α-D-glucopyranoside: a product of host cholesterol efflux promoted by Helicobacter pylori.

机构信息

Department of Chemistry, University of California Davis, One Shields Avenue, Davis, CA 95616, USA.

出版信息

Chem Commun (Camb). 2012 Sep 18;48(72):9083-5. doi: 10.1039/c2cc33948j. Epub 2012 Aug 2.

Abstract

In a three-step protocol involving regioselective enzymatic acylation, per-O-trimethylsilylation, and a one-pot α-glycosidation-deprotection sequence, cholesteryl-6-O-tetradecanoyl-α-D-glucopyranoside (α-CAG) of Helicobacter pylori is afforded starting from glucose in an overall yield of 45%. The production of CAG can be scaled to make purified quantities available to the biological community for the first time.

摘要

在一个涉及区域选择性酶酰化、全三甲基硅醚化和一锅α-糖苷化-脱保护序列的三步法方案中,从葡萄糖出发,以 45%的总收率提供了来自幽门螺杆菌的胆甾醇-6-O-十四烷酰基-α-D-吡喃葡萄糖苷(α-CAG)。CAG 的生产可以扩大规模,使生物界首次获得纯化的 CAG 供试品。

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