从肌醇合成（+）-和（-）-野尻霉素及其1-脱氧衍生物。

Synthesis of (+)- and (-)-nojirimycin and their 1-deoxy derivatives from myo-inositol.

作者信息

Chida N, Furuno Y, Ikemoto H, Ogawa S

机构信息

Department of Applied Chemistry, Faculty of Science and Technology, Keio University, Yokohama, Japan.

出版信息

Carbohydr Res. 1992 Dec 31;237:185-94. doi: 10.1016/s0008-6215(92)84242-k.

DOI:10.1016/s0008-6215(92)84242-k

PMID:1294293

Abstract

The conversion of the naturally abundant cyclitol, myo-inositol (4), into (+)-nojirimycin (1a), its enantiomer (1b), and their 1-deoxy analogues (2a and 2b) is described. Biological assay of 2a, 2b, and the bisulfite adducts of 1a and 1b (3a and 3b) showed that the compounds having the unnatural L-gluco configuration (2b and 3b) possess moderate-to-high inhibitory activity against almond beta-D-glucosidase and bovine liver beta-D-galactosidase.

摘要

本文描述了将天然丰富的环糖醇——肌醇（4）转化为（+）-野尻霉素（1a）、其对映体（1b）及其1-脱氧类似物（2a和2b）的过程。对2a、2b以及1a和1b的亚硫酸氢盐加合物（3a和3b）的生物活性测定表明，具有非天然L-葡萄糖构型的化合物（2b和3b）对杏仁β-D-葡萄糖苷酶和牛肝β-D-半乳糖苷酶具有中度至高度的抑制活性。