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Synthesis and Biological Evaluation of α‐ L ‐Fucosidase Inhibitors: 5a‐Carba‐α‐ L ‐fucopyranosylamine and Related Compounds
Author(s) -
Ogawa Seiichiro,
Maruyama Ayako,
Odagiri Takashi,
Yuasa Hideya,
Hashimoto Hironobu
Publication year - 2001
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200103)2001:5<967::aid-ejoc967>3.0.co;2-j
Subject(s) - fucosidase , chemistry , stereochemistry , iminosugar , amine gas treating , fucose , glycoside hydrolase , inhibitory postsynaptic potential , enzyme , biochemistry , organic chemistry , neuroscience , glycoprotein , biology
5a‐Carba‐α‐ L ‐fucopyranosylamine ( 5 ), an α‐glucosidase inhibitor validamine analog possessing an α‐ L ‐fucose‐type structure, and four related compounds ( 4 and 6 − 8 ) were synthesized and their glycosidase inhibitory potential determined. Carbafucosylamine has already been shown to possess a specific and very strong inhibitory activity against α‐ L ‐fucosidase ( K i = 1.2 × 10 −8 M , bovine kidney). Judging from the activity of the other analogs prepared, this amine might be expected to be a lead compound for development of a new type of α‐ L ‐fucosidase inhibitor.