N-domain selectivity of angiotensin I-converting enzyme as assessed by structure-function studies of its highly selective substrate, N-acetyl-seryl-aspartyl-lysyl-proline

Biochemical Pharmacology

Volumn 57, Issue 6, 1999, Pages 611-618

  Michaud, Annie ^a   Chauvet, Marie Thérèse ^a   Corvol, Pierre ^a  

^a Unite 36 College de France 75005 ^*  (France)

Author keywords

ACE C domain; ACE N domain; AcSDKP; Peptidyl dipeptidase; Stem cells

Indexed keywords

AMINO ACID; DIPEPTIDYL CARBOXYPEPTIDASE; OLIGOPEPTIDE; SERASPENIDE;

ARTICLE; ENZYME ACTIVITY; ENZYME BINDING; ENZYME SUBSTRATE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IN VITRO STUDY; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION;

BINDING SITES; KINETICS; OLIGOPEPTIDES; PEPTIDYL-DIPEPTIDASE A; STRUCTURE-ACTIVITY RELATIONSHIP; SUBSTRATE SPECIFICITY;

EID: 0033560110     PISSN: 00062952     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0006-2952(98)00336-0     Document Type: Article

References (30)

1. Soubrier F., Alhenc-Gélas F., Hubert C., Allegrini J., John M., Tregear G., Corvol P. Two putative active centers in human angiotensin I-converting enzyme revealed by molecular cloning. Proc Natl Acad Sci USA. 85:1988;9386-9390.
2. Williams T.A., Corvol P., Soubrier F. Identification of two active site residues in human angiotensin I-converting enzyme. J Biol Chem. 269:1994;29430-29434.
3. Lattion A.-L., Soubrier F., Allegrini J., Hubert C., Corvol C., Alhenc-Gélas F. The testicular transcript of the angiotensin I-converting enzyme encodes for the ancestral, non-duplicated form of the enzyme. FEBS Lett. 252:1989;99-104.
4. Ehlers M.R.W., Fox E.A., Strydom D.J., Riordan J.F. Molecular cloning of human testicular angiotensin-converting enzyme The testis isozyme is identical to the C-terminal half of endothelial angiotensin-converting enzyme . Proc Natl Acad Sci USA. 86:1989;7741-7745.
5. 2- and COOH-terminal tripeptides from the luteinizing hormone-releasing hormone . Proc Natl Acad Sci USA. 82:1985;1025-1029.
6. Skeggs L.T., Kahn J.R., Shumway N.P. Preparation and function of the hypertension converting enzyme. J Exp Med. 103:1956;295-299.
7. Yang H.-Y.T., Erdös E.G., Levin Y. A dipeptidyl carboxypeptidase that converts angiotensin I and inactivates bradykinin. Biochim Biophys Acta. 214:1970;374-376.
8. Rousseau A., Michaud A., Chauvet M.-T., Lenfant M., Corvol P. The hemoregulatory peptide N-acetyl-Ser-Asp-Lys-Pro is a natural and specific substrate of the N-terminal active site of human angiotensin-converting enzyme. J Biol Chem. 270:1995;3656-3661.
9. Azizi M., Rousseau A., Ezan E., Guyene T.-T., Michelet S., Grognet J.-M., Lenfant M., Corvol P., Ménard J. Acute angiotensin-converting enzyme inhibition increases the plasma level of the natural stem cell regulator N-acetyl-seryl-aspartyl-lysyl-proline. J Clin Invest. 97:1996;839-844.
10. Krege J.H., John S.W.N., Langenbach L.L., Hodgin J.B., Hagaman J.R., Bachman E.S., Jennette J.C., O'Brien D.A., Smithies O. Male-female differences in fertility and blood pressure in ACE-deficient mice. Nature. 375:1995;146-148.
11. Esther C.R., Howard J.T.E., Marino E.M., Goddard J.M., Capecchi M.R., Bernstein K.E. Mice lacking angiotensin-converting enzyme have low blood pressure, renal pathology and reduced male fertility. Lab Invest. 74:1996;953-965.
12. Hagaman J.R., Moyer J.S., Bachman E.S., Sibony M., Magyar P.L., Welch J.E., Smithies O., Krege J.H., O'Brien D.A. Angiotensin-converting enzyme and male fertility. Proc Natl Acad Sci USA. 95:1998;2552-2557.
13. Wei L., Alhenc-Gélas F., Corvol P., Clauser E. The two homologous domains of human angiotensin I-converting enzyme are both catalytically active. J Biol Chem. 266:1991;9002-9008.
14. Jaspard E., Wei L., Alhenc-Gélas F. Differences in the properties and enzymatic specificities of the two active sites of angiotensin I-converting enzyme (kinase II). Studies with bradykinin and other natural peptides. J Biol Chem. 268:1993;9498-9503.
15. Deddish P.A., Marcic B., Jackman H.L., Wang H.-Z., Skidgel R.A., Erdös E.G. N-domain-specific substrate and C-domain inhibitors of angiotensin-converting enzyme angiotensin-(1-7) and keto-ACE . Hypertension. 31:1998;912-917.
16. Michaud A., Williams T.A., Chauvet M.-T., Corvol P. Substrate dependence of angiotensin I-converting enzyme inhibition captopril displays a partial selectivity for inhibition of N-acetyl-seryl-aspartyl-lysyl-proline hydrolysis compared with that of angiotensin I . Mol Pharmacol. 51:1997;1070-1076.
17. Bünning P., Holmquist B., Riordan J. Specificity and kinetic characteristics of angiotensin converting enzyme. Biochemistry. 22:1983;103-110.
18. Cheung H.-S., Wang F.-L., Ondetti M.-A., Sabo E., Cushman D. Binding of peptide substrates and inhibitors of angiotensin-converting enzyme. Importance of the COOH-terminal dipeptide sequence. J Biol Chem. 255:1980;401-407.
19. Pfuetzner R., Chan W.-C. Synergistic binding of ligands to angiotensin-converting enzyme. J Biol Chem. 263:1988;4056-4058.
20. Schechter I., Berger A. On the size of the active site in proteases. I. Papain. Biochem Biophys Res Commun. 27:1967;157-162.
21. Beldent V., Michaud A., Wei L., Chauvet M.T., Corvol P. Proteolytic release of human angiotensin-converting enzyme Localization of the cleavage site . J Biol Chem. 268:1993;26428-26434.
22. Alhenc-Gélas F., Weare J.A., Johnson R.L., Erdös E.G. Measurement of human converting enzyme level by direct radioimmunoassay. J Lab Clin Med. 101:1983;83-96.
23. Cushman D., Cheung H. Spectrophotometric assay and properties of the angiotensin-converting enzyme of rabbit lung. Biochem Pharmacol. 20:1971;1637-1648.
24. Wei L., Alhenc-Gélas F., Soubrier F., Michaud A., Corvol P., Clauser E. Expression and characterization of recombinant human angiotensin I-converting enzyme Evidence for a C-terminal transmembrane anchor and for a proteolytic processing of the secreted recombinant and plasma enzymes . J Biol Chem. 266:1991;5540-5546.
25. Perich R.B., Jackson B., Johnston C.I. Structural constraints of inhibitors for binding at two active sites on somatic angiotensin converting enzyme. Eur J Pharmacol. 266:1994;201-211.
26. Pascard C., Guilhem J., Vincent M., Rémond G., Portevin B., Laubie M. Configuration and preferential solid-state conformations of perindoprilat (S-9780). Comparison with the crystal structures of other ACE inhibitors and conclusions related to structure-activity relationships. J Med Chem. 34:1991;663-669.
27. Danilov S., Jaspard E., Churakova T., Towbin H., Savoie F., Wei L., Alhenc-Gélas F. Structure-function analysis of angiotensin I-converting enzyme using monoclonal antibodies. Selective inhibition of the amino-terminal active site. J Biol Chem. 269:1994;26806-26814.
28. Ryan J.W. Angiotensin-converting enzyme, dipeptidyl carboxypeptidase I, and its inhibitors. Methods Enzymol. 163:1988;194-210.
29. Skidgel R.A., Defendini R., Erdös E.G. Angiotensin I converting enzyme and its role in neuropeptide metabolism. Turner A.J., Neuropeptides and Their Peptidases. 1987;165-182 Ellis Horwood Ltd, Chichester, UK.
30. Gaudron S., Adeline M.-T., Potier P., Thierry J. NAcSDKP analogues resistant to angiotensin-converting enzyme. J Med Chem. 40:1997;3963-3968.