糖基化壳聚糖A和B的化学酶法合成。

Chemoenzymatic synthesis of sacranosides a and B.

作者信息

Kawahara Eiji, Fujii Mikio, Ida Yoshiteru, Akita Hiroyuki

机构信息

School of Pharmaceutical Sciences, Toho University, Funabashi, Chiba, Japan.

出版信息

Chem Pharm Bull (Tokyo). 2006 Mar;54(3):387-90. doi: 10.1248/cpb.54.387.

DOI:10.1248/cpb.54.387

PMID:16508199

Abstract

Direct beta-glucosidation between (-)-myrtenol and nerol and D-glucose (3) using the immobilized beta-glucosidase from almonds with the synthetic prepolymer ENTP-4000 gave myrtenyl O-beta-D-glucoside (4) and neryl O-beta-D-glucoside (10), respectively. The coupling of the myrtenyl or neryl O-beta-D-glucopyranoside congeners (7 or 13) and 2,3,4-tri-O-benzoyl-beta-L-arabinopyranosyl bromide (8) afforded the coupled products (9 or 14), respectively. Deprotection of the coupled products (9 or 14) afforded the synthetic myrtenyl 6-O-alpha-L-arabinopyranosyl-beta-D-glucopyranoside (Sacranoside A, 1) or neryl 6-O-alpha-L-arabinopyranosyl-beta-D-glucopyranoside (Sacranoside B, 2), respectively.

摘要

使用杏仁固定化β-葡萄糖苷酶与合成预聚物ENTP-4000，使（-）-桃金娘烯醇与橙花醇和D-葡萄糖（3）直接进行β-葡萄糖苷化反应，分别得到桃金娘烯基O-β-D-葡萄糖苷（4）和橙花烯基O-β-D-葡萄糖苷（10）。桃金娘烯基或橙花烯基O-β-D-吡喃葡萄糖苷类似物（7或13）与2,3,4-三-O-苯甲酰基-β-L-阿拉伯吡喃糖基溴（8）偶联，分别得到偶联产物（9或14）。偶联产物（9或14）脱保护后，分别得到合成的桃金娘烯基6-O-α-L-阿拉伯吡喃糖基-β-D-吡喃葡萄糖苷（Sacranoside A，1）或橙花烯基6-O-α-L-阿拉伯吡喃糖基-β-D-吡喃葡萄糖苷（Sacranoside B，2）。