Reactions of N-(o-carboxybenzoyl)-L-leucine: Intramolecular catalysis of amide hydrolysis and imide formation by two carboxy groups

Journal of the Chemical Society. Perkin Transactions 2

Volumn 1, Issue 9, 2001, Pages 1863-1868

  Onofrio, Alvaro B ^a   Gesser, José C ^a   Joussef, Antonio C ^a   Nome, Faruk ^a  

^a FEDERAL UNIVERSITY OF SANTA CATARINA   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; HYDROLYSIS; PH EFFECTS; RATE CONSTANTS; SOLUTIONS;

ENZYMATIC CATALYSIS;

ENZYMES;

EID: 0034741444     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: 10.1039/b007047p     Document Type: Article

References (24)

1. S. F. Yunes, J. C. Gesser, H. Chaimovich, F. Nome J. Phys. Org. Chem. 1997 10 461.
2. V. G. Machado, F. Nome Chem. Commun. 1997 19 1917.
3. V. G. Machado, C. Bunton, C. Zucco, F. Nome J. Chem. Soc., Perkin Trans. 2 2000 169.
4. M. L. Bender, Y.-L. Chow, F. Chloupek J. Am. Chem. Soc. 1958 80 5380.
5. M. N. Khan J. Phys. Org. Chem. 1998 11 216.
6. M. N. Khan J. Chem. Soc., Perkin Trans. 2 1989 233.
7. A. J. Kirby Angew. Chem., Int. Ed. Engl. 1996 35 709.
8. M. F. Aldersley, A. J. Kirby, P. W. Lancaster, R. S. McDonald, C. R. Smith J. Chem. Soc., Perkin Trans. 2 1974 1487.
9. A. J. Kirby, R. S. McDonald, C. R. Smith J. Chem. Soc., Perkin Trans. 2 1974 1495.
10. M. F. Aldersley, A. J. Kirby, P. W. Lancaster J. Chem. Soc., Perkin Trans. 2 1974 1504.
11. A. J. Kirby, P. W. Lancaster J. Chem. Soc. Perkin Trans. 2 1972 1206.
12. M. D. Hawkins J. Chem. Soc., Perkin Trans. 2 1976 642.
13. F. M. Menger, M. Ladika J. Am. Chem. Soc. 1988 110 6794.
14. C. J. Perry J. Chem. Soc., Perkin Trans. 2 1997 977.
15. R. M. A. Blackburn, B. Capon, A. C. McRitchie Bioorg. Chem. 1977 6 71.
16. H. Morawetz, J. A. Shafer J. Am. Chem. Soc. 1962 84 3783.
17. M. I. Page and A. Williams Enzyme Mechanisms, Royal Society of Chemistry, London, 1987, p. 230.
18. A. B. Onofrio, A. C. Joussef, F. Nome Synth. Commun. 1999 29 3039.
19. A. K. Bose Org. Synth. 1960 40 82.
20. A. I. Vogel Textbook of Practical Organic Chemistry, Longman Scientific and Technical, London, 1989 1385.
21. J. Brow, S. C. Su, J. A. Shafer J. Am. Chem. Soc. 1966 88 4468.
22. D. D. Perry, B. Dempsey and E. P. Serjeant pKa Prediction for Organic Acids and Bases, Chapman and Hall, London, 1981, p. 16, 51, 55, 127.
23. R. S. Brown, A. J. Bennet, H. Slebocka-Tilk Acc. Chem. Res. 1992 25 (11) 481.
24. J. B. Capindale, H. S. Fan Can. J. Chem. 1967 45 1921.