2-hydroxycastanospermines (dihydroxy-L-swainsonines) from octonolactones: Inhibition of naringinase (L-rhamnosidase)
2-hydroxycastanospermines (dihydroxy-L-swainsonines) from octonolactones: Inhibition of naringinase (L-rhamnosidase)
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DOI：
10.1016/0040-4039(96)01956-9
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发表时间：
1996-11-18
影响因子：
1.8
通讯作者：
Fleet, GWJ
中科院分区：
文献类型：
--
作者：
Bell, AA;Pickering, L;Fleet, GWJ
2S-2-羟基栗精胺和2 R-和2S-2-羟基-6-表栗精胺（其中有6个相邻的手性中心和8个连续的碳原子含有来自八碳糖内酯的官能团）的短合成依赖于有效的环化以得到具有反式丙酮化物作为保护基的哌啶。2S-2-羟基-6-表栗精胺和2S-2-羟基栗精胺对柚苷酶（L-鼠李糖苷酶）的抑制作用可能是由于其结构类似于非天然的L-（+）-苦马豆素。版权所有（C）1996 Elsevier Science Ltd
Short syntheses of 2S-2-hydroxycastanospermine, and 2R- and 2S-2-hydroxy-6-epicastanospermine - in which there are 6 adjacent chiral centres and 8 contiguous carbon atoms containing functional groups from eight carbon sugar lactones - depend on efficient cyclisations to give piperidines with trans-acetonides as protecting groups. Inhibition of naringinase (L-rhamnosidase) by 2S-2-hydroxy-6-epicastanospermine and 2S-2-hydroxycastanospermine may be due to a structural resemblance to the unnatural L-(+)-swainsonine. Copyright (C) 1996 Elsevier Science Ltd