α- and β-homogalactonojirimycins (α- and β-homogalactostatins):: Synthesis and further biological evaluation
α- and β-homogalactonojirimycins (α- and β-homogalactostatins):: Synthesis and further biological evaluation
复制标题
DOI：
10.1016/s0968-0896(00)00343-6
复制
发表时间：
2001-05-01
影响因子：
3.5
通讯作者：
Asano, N
中科院分区：
文献类型：
--
作者：
Martin, OR;Saavedra, OM;Asano, N
高亚氨基糖α-和β-高半乳糖基野尻霉素是从一个共同的中间体，四-O-苄基-D-半乳糖基-庚烯醇6，通过高度立体选择性的反应序列，包括，作为关键步骤，一个内部的氨基汞（α-差向异构体）和一个双重还原胺化（β-差向异构体）。α-高半乳糖野尻霉素保留了母体半乳糖野尻霉素和1-脱氧半乳糖野尻霉素作为α-半乳糖苷酶抑制剂的大部分有效活性。然而，与母体亚胺糖相比，它不抑制β-半乳糖苷酶，但刀豆酶除外。β-高半乳糖野尻霉素是一种弱α-半乳糖苷酶抑制剂，对β-半乳糖苷酶完全没有活性。因此，通过在母体亚氨基糖的结构中添加α-CH 2 OH基团，已经实现了对一个酶家族的显著选择性。(C)2001爱思唯尔科技有限公司版权所有。
The homoiminosugars alpha- and beta -homogalactonojirimycins were prepared from a common intermediate, tetra-O-benzyl-D-galacto-heptenitol 6, by way of highly stereoselective reaction sequences involving, as the key steps, an internal amidomercuralion (a-epimer) and a double reductive amination (beta -epimer). alpha -Homogalactonojirimycin retains a large part of the potent activity of the parent galactonojirimycin and 1-deoxygalactonojirimycin as an inhibitor of alpha -galaclosidases. However, by contrast with the parent iminosugars, it does not inhibit beta -galactosidases, with the exception of the Jack beans enzyme. beta -Homogalactonojirimycin is a weak cc-galactosidase inhibitor and is completely devoid of activity towards P-galactosidases. Thus, a marked selectivity toward one family of enzymes has been achieved by the addition of an alpha -CH2OH group in the structure of the parent iminosugars. (C) 2001 Elsevier Science Ltd. All rights reserved.