从（-）-维博-槲皮醇设计与合成糖苷酶抑制剂5-氨基-1,2,3,4-环己烷四醇衍生物。

Design and synthesis of glycosidase inhibitor 5-amino-1,2,3,4-cyclohexanetetrol derivatives from (-)-vibo-quercitol.

作者信息

Ogawa Seiichiro, Asada Miwako, Ooki Yoriko, Mori Midori, Itoh Masayoshi, Korenaga Takashi

机构信息

Department of Biosciences and Informatics, Faculty of Science and Technology, Keio University, Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan.

出版信息

Bioorg Med Chem. 2005 Jul 1;13(13):4306-14. doi: 10.1016/j.bmc.2005.04.003.

DOI:10.1016/j.bmc.2005.04.003

PMID:15878669

Abstract

In continuation of development of bioactive inositol derivatives, a 1-O-methyl derivative of 5-amino-5-deoxy-L-talo-quercitol was designed and synthesized as an analogue of the strong alpha-fucosidase inhibitor, 5a-carba-alpha-L-fucopyranosylamine, the methyl branch being replaced with methoxyl, and demonstrated to be a moderate alpha-fucosidase inhibitor. The present approach provides a possible route to apply alkyl ethers of aminodeoxyinositols as hexopyranose mimics of biological interest.

摘要

在生物活性肌醇衍生物的持续研发中，设计并合成了5-氨基-5-脱氧-L-塔罗-奎糖醇的1-O-甲基衍生物，作为强效α-岩藻糖苷酶抑制剂5a-碳环-α-L-呋喃岩藻糖胺的类似物，其中甲基支链被甲氧基取代，并证明其为中度α-岩藻糖苷酶抑制剂。本方法为将氨基脱氧肌醇的烷基醚用作具有生物学意义的己吡喃糖模拟物提供了一条可能的途径。