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J Med Chem. 1993 Apr 2;36(7):883-7.

Adenosine-5'-carboxaldehyde: a potent inhibitor of S-adenosyl-L-homocysteine hydrolase.

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1
Department of Medicinal Chemistry, University of Kansas, Lawrence 66045.

Abstract

Adenosine-5'-carboxaldehyde (3) and its 4'-epimer (4) were synthesized and shown to be potent type I mechanism-based inhibitors of recombinant rat liver AdoHcy hydrolase with k2/KI values of 16.7 x 10(-3) and 5.5 x 10(-3) nM-1 min-1, respectively. The observation that 3 and 4 are potent inhibitors of AdoHcy hydrolase supports the hypothesis that they function as key intermediates in the mechanism by which the (Z)- and (E)-4',5'-didehydro-5'-deoxy-5'-fluoroadenosines 1 and 2 inactivate this enzyme.

PMID:
8464042
DOI:
10.1021/jm00059a013
[Indexed for MEDLINE]

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