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Synthesis and Glycosidase Inhibitory Activity of Five Stereoisomers of 5‐Amino‐5‐ C ‐methyl‐1,2,3,4‐cyclopentanetetrol
Author(s) -
Ogawa Seiichiro,
Washida Kenji
Publication year - 1998
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/(sici)1099-0690(199809)1998:9<1929::aid-ejoc1929>3.0.co;2-c
Subject(s) - chemistry , stereochemistry , glycoside hydrolase , amino acid , inhibitory postsynaptic potential , enzyme , organic chemistry , biochemistry , neuroscience , biology
Abstract In order to elucidate the essential core structure of potent α‐mannosidase inhibitors, e.g. mannostatin A, 5‐amino‐5‐ C ‐methyl‐1,2,3,4‐cyclopentanetetrols 4‐8 were designed and synthesized by a base‐catalyzed nitro aldol condensation of nitroethane and the dialdehyde derived by periodate oxidation of DL ‐1,2‐ O ‐cyclohexylidene‐ myo ‐inositol, followed by reduction and deprotection. Biological assay of the five stereoisomers thus obtained for the six glycosidases has demonstrated the DL ‐(1,2/3,4,5) and (1,2,3,4,5/0) isomers to be moderate α‐mannosidase inhibitors, suggesting that the all‐cis configuration of the amino and three hydroxy groups on the cyclopentane ring plays a role in exhibiting inhibitory activity.