甘露糖基三糖的碳环类似物的合成：醚键和亚氨基连接的3,6-双（5a-碳杂-α-D-甘露吡喃糖基）-3,6-二脱氧-α-D-甘露吡喃糖苷。

Synthesis of carbocyclic analogues of the mannosyl trisaccharide: ether- and imino-linked methyl 3,6-bis(5a-carba-alpha-D-mannopyranosyl)-3,6-dideoxy-alpha-D-mannopyran osides.

作者信息

Ogawa S, Sasaki S, Tsunoda H

机构信息

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

出版信息

Carbohydr Res. 1995 Sep 8;274:183-96. doi: 10.1016/0008-6215(95)00121-9.

DOI:10.1016/0008-6215(95)00121-9

PMID:7585705

Abstract

Carbocyclic analogues 2 and 3 of the "trimannosyl structure 1", methyl 3,6-bis(5a-carba-alpha-D-mannopyranosyl)-3,6-dideoxy-alpha-D-ma nnopyranosides bonded by way of respective ether and imino linkages, were synthesized. The ether 2 had no inhibitory activity against alpha-D-mannosidase; in contrast, the imino compound 3 was a mild inhibitor. Furthermore, the inhibitory activity of 4, related to 3 by introduction of unsaturation between C-5 and C-5a of the carba-sugar moieties, was shown to be somewhat greater.

摘要

合成了“三甘露糖基结构1”的碳环类似物2和3，即通过各自的醚键和亚氨基键连接的3,6 - 双（5a - 碳 - α - D - 甘露吡喃糖基）- 3,6 - 二脱氧 - α - D - 甘露吡喃糖苷甲酯。醚类化合物2对α - D - 甘露糖苷酶没有抑制活性；相比之下，亚氨基化合物3是一种温和的抑制剂。此外，通过在碳糖部分的C - 5和C - 5a之间引入不饱和键与3相关的化合物4，其抑制活性略高。