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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 22, Number 11
BKCSDE 22(11)
November 20, 2001 

Inhibition of Carboxypeptidase A with β-Lactone-bearing Phenylalanine. Design, Synthesis, and Stereochemistry-dependent Inhibition Mode
Mijoon Lee, Dong H. Kim
Inhibition stereochemistry, Inhibitor design strategy, b-Lactone, Carboxypeptidase A.
(3S,1'S)-3-(1'-Carboxy-2'-phenyl)ethylamino-2-oxetanone (1a) and (3R,1'S)-3-(1'-carboxy-2'-phenyl)ethylamino-2-oxetanone (1b) were designed, synthesized, and evaluated as inhibitors for carboxypeptidase A, a prototypical zinc protease that removes the C-terminal amino acid having an aromatic side chain from oligopeptide substrate. It was concluded from the analysis of inhibition kinetics that while 1a inactivates CPA irreversibly, its diastereoisomer, 1b is a weak competitive inhibitor for CPA. A possible explanation for the observed difference in inhibition mode that is dependent on the inhibitor stereochemistry is offered.
1236 - 1242
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