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Chemical Modification of the α‐Mannosidase Inhibitor Mannostain A: Synthesis of a Potent Inhibitor 1 L ‐(1,2,3,5/4)‐5‐Amino‐4‐ O ‐methyl‐1,2,3,4‐cyclopentanetetrol
Author(s) -
Ogawa Seiichiro,
Morikawa Takayuki
Publication year - 2005
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/ejoc.200500118
Subject(s) - chemistry , mannosidase , inhibitory postsynaptic potential , stereochemistry , biochemistry , enzyme , neuroscience , biology
Demethylthio‐, S ‐demethyl‐, and S ‐ethyl derivatives of the α‐mannosidase inhibitor, mannostasin A, were synthesized and evaluated for their inhibition of Jack bean α‐mannosidase with the prime objective of elucidating the role of the methylthio group. All methylthio derivatives had significantly lowered inhibitory potentials. However, one mannostatin A analogue with a methoxyl instead of the methylthio group exhibited about twofold enhancement of the activity. The structure and inhibitory activity relationships of mannostatin A and related compounds are discussed in light of our results. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)