共 32 条
Synthesis of thioswainsonine as a potential glycosidase inhibitor
被引:12
作者:
Kumar, Nag S.
[1
]
Pinto, B. Mario
[1
]
机构:
[1] Simon Fraser Univ, Dept Chem, Burnaby, BC V5A 1S6, Canada
基金:
加拿大自然科学与工程研究理事会;
关键词:
glycosidase inhibitor;
swainsonine analogue;
bicyclic sulfonium salt;
indolizidine alkaloid analogue;
D O I:
10.1016/j.carres.2006.04.009
中图分类号:
Q5 [生物化学];
Q7 [分子生物学];
学科分类号:
071010 ;
081704 ;
摘要:
The synthesis of a bicyclic sulfonium-ion analogue of a naturally occurring glycosidase inhibitor, swainsonine, in which the bridgehead nitrogen atom is replaced by a sulfonium ion, has been achieved by a multi-step synthesis starting from 1,4-anhydro2,3-di-O-benzyl-4-thio-D-lyxitol. The synthetic strategy relies on the intramolecular displacement of a leaving group on a pendant acyclic chain by a cyclic thioether. This bicyclic sulfonium salt will serve as a candidate to test the hypothesis that a sulfonium salt carrying a permanent positive charge would be an effective glycosidase inhibitor. (c) 2006 Elsevier Ltd. All rights reserved.
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页码:1685 / 1691
页数:7
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