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J. Biochem, 1984, Vol. 95, No. 6 1819-1821
© 1984 Japanese Biochemical Society

research-article

N-Benzyloxycarbonyl-Valyl-Prolinal, a Potent Inhibitor of Post-Proline Cleaving Enzyme1

Hideyoshi YOKOSAWA*, Makoto NISHIKATA** and Shin-ichi ISHII*

*Department of Biochemistry, Faculty of Pharmaceutical Sciences Kita-ku, Sapporo, Hokkaido 060
**Central Research Division, School of Dentistry, Hokkaido University Kita-ku, Sapporo, Hokkaido 060

A peptide aldehyde inhibitor possessing prolinal at the carboxyl terminus was designed as an inhibitor of post-proline cleaving enzyme by analogy with peptide aldehyde inhibitors of serine and thiol proteases. N-Benzyloxycarbonyl-valyl-prolinal was found to be a potent inhibitor of post-proline cleaving enzyme from ascidian sperm with a K1 value of 2.4 nM. The presence of the aldehyde portion of the inhibitor, as well as its prolonged incubation with the enzyme, is indispensable for the potent inhibitory activity of the inhibitor. These results indicate that N-benzyloxycarbonyl-valyl-prolinal functions as a transition-state aldehyde inhibitor of post-proline cleaving enzyme.

1This work was supported in part by Grants-in-Aid for Scientific Research from the Ministry of Education, Science and Culture of Japan, and the Naito Foundation.


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