O-(Hydroxyacetyl)-L-β-phenyllactic acid as a new type of mechanism-based inactivator for carboxypeptidase A

Bioorganic and Medicinal Chemistry Letters

Volumn 7, Issue 20, 1997, Pages 2607-2612

  Kim, Dong ^a   Lee, Kyung Joo ^a  

^a Pohang University of Science and Technology (POSTECH)   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYPEPTIDASE A; ENZYME INHIBITOR;

ARTICLE; CRYSTAL STRUCTURE; DRUG POTENCY; DRUG SYNTHESIS; ENZYME ACTIVITY; ENZYME INACTIVATION; ENZYME KINETICS; X RAY CRYSTALLOGRAPHY;

EID: 0030700360     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(97)10031-2     Document Type: Article

References (23)

1. Silverman, R. B. Mechanism-Based Enzyme Inactivation: Chemistry and Enzymology; CRC Press: Boca Raton, Florida, 1988; Vols I and II.
2. (a) Kim, D. H.; Kim, K. B. J. Am. Chem. Soc. 1991, 113, 3200 - 3202.
3. (b) Kim, D. H.; Chung, S. J. Bioorg. Med. Chem. Lett. 1995, 5, 1667 - 1672.
4. (c) Lee, K. J.; Kim, D. H. Bioorg. Med. Chem. Lett. 1996, 6, 2431 - 2436.
5. Kim, D. H.; Li, Z.-H. Bioorg. Med. Chem. Lett. 1994, 4, 2297 - 2302.
6. (e) Kim, D. H.; Ryoo, J. J. Bioorg. Med. Chem. Lett. 1995, 5, 1287 - 1292.
7. (a) Hartsuck, J. A.; Lipscomb, W. N. In Enzymes, 3rd ed.; Boyer, P. D. Ed.; Academic: New York, 1971, Vol 3, pp 1 - 56.
8. (b) Christianson, D. W.; Lipscomb, W. N. Acc. Chem. Res. 1989, 22, 62 -69.
9. Kim, D. H.; Kim, K. S.; Park, J. K. Bull. Korean Chem. Soc. 1994, 15, 805 - 807.
10. (a) Makinen, M. W.; Fukuyama, J. M.; Kuo, L. C. J. Am. Chem. Soc. 1982, 104, 2667 - 2669.
11. (b) Sander, M. E.; Witzel, H. Biochem. Biophys. Res. Commun. 1985, 132, 681 - 687.
12. (a) Breslow, R.; Wernick, D. L. Proc. Natl. Acad. Sci. U.S.A. 1977, 74, 1303 - 1307.
13. (b) Galdes, A.; Auld, D. S.; Vallee, B. L. Biochemistry 1986, 25, 646 - 651.
14. Christianson, D. W.; Lipscomb, W. N. Proc. Natl. Acad. Sci. U.S.A. 1986, 83, 7568 - 7572.
15. The formation of the anhydride intermediate in the interaction of HPLA with the enzyme is expected from the anhydride mechanism but may also be envisioned from the general base pathway under the conditions of no catalytic water being present. In fact, it has been generally believed that the hydrolysis of ester susbstrate goes through anhydride intermediate:
16. (a) Breslow, R.; Wernick, D. L. Proc. Natl. Acad. Sci. U.S.A. 1987, 74, 1303 - 1307.
17. (b) Makinen, M. W.; Kuo, L. C.; Dymowski, J. D.; Jaffer, S. J. Biol. Chem. 1979, 254, 356 - 366.
18. (c) Breslow, R.; Schepartz, A. Chem. Lett. 1987, 1 - 4.
19. (d) Britt, B. M.; Peticolas, W. L. J. Am. Chem. Soc. 1992, 114, 5295 - 5303.
20. 5: 224.0685, Found: 224.0685.
21. Byers, L. D.; Wolfenden, R. Biochemistry 1973, 12, 2070 - 2078.
22. Kitz, R.; Wilson, I. B. J. Biol. Chem. 1962, 237, 3245 - 3249.
23. Dixon, M. Biochem. J. 1953, 55, 170 - 171.