ISSN:
1434-193X
Keywords:
Cyclitols
;
Aminocyclitols
;
Glycosidase inhibitors
;
α-Mannosidase inhibitors
;
Aldol reaction
;
Chemistry
;
General Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
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.
Type of Medium:
Electronic Resource
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