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A Selective α ‐ L ‐Fucosidase Inhibitor Based on an Aminocyclopentane Framework
Author(s) -
Blaser Adrian,
Reymond JeanLouis
Publication year - 1999
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/(sici)1522-2675(19990505)82:5<760::aid-hlca760>3.0.co;2-s
Subject(s) - chemistry , methylcyclopentane , fucosidase , iminosugar , trichlorosilane , stereochemistry , combinatorial chemistry , biochemistry , organic chemistry , catalysis , enzyme , galactose , platinum , fucose , silicon
(1 R ,2 R ,3 R ,4 S ,5 R )‐4‐amino‐5‐methylcyclopentane‐1,2,3‐triol ( 1 ) was prepared stereoselectively from D ‐ribose ( Scheme ). Aminocyclopentanetriol 1 , which by its design may be considered an analog of the fucosyl cation, inhibits α ‐ L ‐fucosidase selectively ( K i =28 μ M ) over α ‐ and β ‐glucosidase, α ‐ and β ‐mannosidase, and α ‐ and β ‐galactosidase ( Table ).