Kinetics of diketopiperazine formation using model peptides

Journal of Pharmaceutical Sciences

Volumn 87, Issue 3, 1998, Pages 283-288

  Goolcharran, Chimanlall ^a   Borchardt, Ronald T ^a  

^a UNIVERSITY OF KANSAS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PIPERAZINEDIONE;

AMINO TERMINAL SEQUENCE; ARTICLE; CARBOXY TERMINAL SEQUENCE; CATALYSIS; DRUG BIOAVAILABILITY; FOOD PROCESSING; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROLYSIS; MODEL; NONHUMAN; PEPTIDE SYNTHESIS;

EID: 0031897939     PISSN: 00223549     EISSN: None     Source Type: Journal    
DOI: 10.1021/js970325m     Document Type: Article

References (32)

1. Battersby, J. E.; Hancock, W. S.; Canova-Davis, E.; Oeswein, J.; O'Connor, B. Diketopiperazine formation and N-terminal degradation in recombinant human growth hormone. Int. J. Pept. Protein Res. 1994, 44, 215-222.
2. Kertscher, U.; Bienert, M.; Krause, E.; Sepetov, N. F.; Mehlis, B. Spontaneous chemical degradation of substance P in the solid phase and in solution. Int. J. Pept. Protein Res. 1993, 41, 207-221.
3. Beyermann, M.; Bienert, M.; Niedrich, H.; Carpino, L. A.; Sadat-Aalace, D. Rapid continuous peptide synthesis via FMOC amino acid chloride coupling and 4-(aminomethyl)-piperidine deblocking. J. Org. Chem. 1990, 55, 721-728.
4. Purdie, J. E.; Benoiton, N. L. Piperazinedione formation from esters of dipeptides containing glycine, alanine, and sarcosine: The kinetics in aqueous solution. J. Chem. Soc. Perkin Trans. 2 1973, 13, 1845-1852.
5. Skwierczynski, R. D.; Connors, K. A. Demethylation kinetics of aspartame and L-phenylalanine methyl ester in aqueous solution. Pharm. Res. 1993, 10, 1174-1180.
6. Gu, L.; Strickley, R. G. Diketopiperazine formation, hydrolysis, and epimerization of the new dipeptide angiotensin-converting enzyme inhibitor RS-10085. Pharm. Res. 1987, 4, 392-397.
7. Moss, J.; Bundgaard, H. Kinetics and mechanism of the facile cyclization of histidyl-prolineamide to cyclo(His-Pro) in aqueous solution and the competitive influence of human plasma. J. Pharm. Pharmacol. 1990, 42, 7-12.
8. Miyashita, K.; Murakami, M.; Yamada, M.; Iriuchijima, T.; Mori, M. Histidyl-proline diketopiperazine. J. Biol. Chem. 1993, 268, 20863-20865.
9. Steinberg, S. M.; Bada, J. L. Peptide decomposition in the neutral pH region via the formation of diketopiperazines. J. Org. Chem. 1983, 48, 2295-2298.
10. Steinberg, S. M.; Bada, J. L. Diketopiperazine formation during investigations of amino acid racemization in dipeptides. Science 1981, 213, 544-545.
11. Bodanszky, M.; Martinez, J. In The Peptides: Analysis, Synthesis, Biology; Gross, E., Meienhoffer, J., Eds.; Academic Press Inc.: New York, 1983; Vol. 5, pp 120-123, 193-196.
12. Gerig, J. T.; McLeod, R. S. Attempted synthesis of 2-methylalanyl-L-prolyl-L-tryptophan. An unexpected result. J. Org. Chem. 1976, 41, 1653-1655.
13. Gisin, B. F.; Merrifield, R. B. Carboxyl-catalyzed intramolecular aminolysis. A side reaction in solid-phase peptide synthesis. J. Am. Chem. Soc. 1972, 94, 3102-3106.
14. Mazurov, A. A.; Andronati, S. A.; Korotenko, T. I.; Gorbatyuk, V. Y.; Shapiro, Y. E. Formation of pyroglutamylglutamine (or asparagine) diketopiperazine in 'non-classical' conditions: A side reaction in peptide synthesis. Int. J. Pept. Protein Res. 1993, 42, 14-19.
15. Meienhoffer, J. Syntheses of actinomycin and analogues. III. A total synthesis of actinomycin D (C1) via peptide cyclization between proline and sarcosine. J. Am. Chem. Soc. 1970, 92, 3771-3777.
16. Fields, G. B.; Noble, R. L. Solid-phase peptide synthesis utilizing 9-fluorenylmethoxycarbonyl amino acid. Int. J. Pept. Protein Res. 1990, 35, 16-214.
17. Sepetov, N. F.; Krymsky, M. A.; Ovchinnikov, M. V.; Bespalova, Z. D.; Isakova, O. L.; Soueek, M.; Lebl, M. Rearrangement, racemization and decomposition of peptides in aqueous solution. Pept. Res. 1991, 4, 308-313.
18. Straub, J. A.; Akiyama, A.; Parmar, P.; Musso, G. F. Chemical pathways of the bradykinin analogue, RMP-7. Pharm. Res. 1995, 12, 305-308.
19. Oyler, A. R.; Naldi, R. E.; Lloyd, J. R.; Graden, D. A.; Shaw, C. J. Characterization of the solution degradation products of Histrelin, a gonadotropin releasing hormone (LH/RH) agonist. J. Pharm. Sci. 1991, 80, 271-275.
20. Radzicka, A.; Wolfenden, R. Rates of uncatalyzed peptide bond hydrolysis in neutral solution and the transition state affinities of proteases. J. Am. Chem. Soc. 1996, 118, 6105-6109.
21. Jenks, W. P. In Catalysis in Chemistry and Enzymology; McGraw-Hill: New York, 1969; pp 163-195.
22. Bruice, T. C.; Bradbury, W. C. The gem effect. The influence of 3-mono- and 3,3-disubstitution on the rates of solvolysis of mono-p-bromophenyl glutarate. J. Am. Chem. Soc. 1965, 87, 4846-4850.
23. Higuchi, T.; Eberson, L.; McRae, J. D. Acid anhydride-free acid equilibria in water in some substituted succinic scid systems and their interaction with aniline. J. Am. Chem. Soc. 1967, 89, 3001-3004.
24. Borchardt, R. T.; Cohen, L. A. Stereopopulation Control. II. Rate enhancement of intramolecular nucleophilic displacement. J. Am. Chem. Soc. 1972, 94, 9166-9174.
25. Borchardt, R. T.; Cohen, L. A. Stereopopulation Control. III. Facilitation of intramolecular conjugate addition of the carboxyl group. J. Am. Chem. Soc. 1972, 94, 9175-9182.
26. Levitt, M. Effect of proline residues on protein folding. J. Mol. Biol. 1981, 145, 251-263.
27. Stein, R. L. In Advances in Protein Chemistry; Afinsen, C. B., Edsall, J. T., Richards, F. M., Eisenberg, D. S., Eds.; Academic Press, Inc.: New York, 1993; Vol. 44.
28. Ramachandran, G. N.; Mitra, A. K. An explanation for the rare occurrence of cis peptide units in proteins and polypeptides. J. Mol. Biol. 1976, 107, 85-92.
29. Stewart, D. E.; Sarkar, A.; Wampler, J. E. Occurrence and role of cis peptide bonds in protein structures. J. Mol. Biol. 1990, 214, 253-260.
30. Ciarkowski, J.; Gdaniec, M.; Kolodziejczyk, A.; Liberek, B.; Borremans, F. A. M.; Anteunis, M. J. O. Conformation of cyclo-(D-phenylalanyl-trans-4-fluoro-D-prolyl). Int. J. Pept. Protein Res. 1990, 36, 285-291.
31. Budesinsky, M.; Symersky, J.; Jency, J.; VanHecke, J.; Hosten, N.; Anteunis, M.; Borremans, F. A. M. Cyclo (L-propyl-L-N-methylphenylalanyl). Conformation in solution and in the crystal. Int. J. Pept. Protein Res. 1992, 39, 123-130.
32. Liwo, A.; Ciakowski, J. Origin of the ring-ring interaction in cyclic dipeptides incorporating an aromatic amino acid. Tetrahedron Lett. 1985, 26, 1873-1876.