Urethane-protected N-carboxyanhydrides (UNCAs) as unique reactants for the study of intrinsic racemization tendencies in peptide synthesis

Journal of Peptide Research

Volumn 49, Issue 4, 1997, Pages 281-292

  Romoff, Todd T ^a,b   Goodman, Murray ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b AFFYMAX RESEARCH INSTITUTE   (United States)

Author keywords

Hindered peptide bond formation; Racemization; Tertiary amines; Urethane protected N carboxyanhydride

Indexed keywords

ACID ANHYDRIDE; SYNTHETIC PEPTIDE; URETHAN;

ARTICLE; CHEMICAL BINDING; PEPTIDE SYNTHESIS; PRIORITY JOURNAL; RACEMIC MIXTURE; REACTION ANALYSIS; STEREOISOMERISM;

EID: 0030947731     PISSN: 1397002X     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1399-3011.1997.tb01128.x     Document Type: Article

References (26)

1. A comprehensive review of racemization studies up to 1979 is given by Kemp, D.S. (1979) in The Peptides. Analysis, Synthesis, Biology. (Gross, E. & Meienhofer, J., eds.), vol. 1, pp. 315-383, Academic Press, Orlando. A more recent review is given by Bodanszky, M. (1993) Principles of Peptide Synthesis, 2nd rev. ed., Springer-Verlag, Berlin
2. A comprehensive review of racemization studies up to 1979 is given by Kemp, D.S. (1979) in The Peptides. Analysis, Synthesis, Biology. (Gross, E. & Meienhofer, J., eds.), vol. 1, pp. 315-383, Academic Press, Orlando. A more recent review is given by Bodanszky, M. (1993) Principles of Peptide Synthesis, 2nd rev. ed., Springer-Verlag, Berlin
3. For a review of the preparation and reactions of UNCAs, see Fuller, W.D., Goodman, M., Naider, F. & Zhu, Y.-F. (1996) Biopolymers (Peptide Science), 40, 183-205
4. Scott, F.L., Glick, R.E. & Winstein, S. (1957) Experientia 13, 183-185
5. A review of the reactions of 5(4H)-oxazolones, including studies on the kinetics of racemization and aminolysis is given by Goodman, M. & Glaser, A. (1970) in Peptides. Proceedings of the First American Peptide Symposium (Weinstein, B. & Lande, S., eds.), pp. 267-335, Marcel Dekker, New York
6. Benoiton, N.L. (1996) Biopolymers (Peptide Science) 40, 245-254
7. Fuller, W.D., Cohen, M.P., Shabankareh, M., Blair, R.K., Goodman, M. & Naider, F.R. (1990) J. Am. Chem. Soc. 112, 7414-7416
8. For example, (a) Bodanszky, M. & Bodanszky, A. (1967) Chem. Commun. 591-593; (b) Williams, M.W. & Young, G.T. (1972) J. Chem. Soc. Perkin Trans. 1, 1194-12009
9. For example, (a) Bodanszky, M. & Bodanszky, A. (1967) Chem. Commun. 591-593; (b) Williams, M.W. & Young, G.T. (1972) J. Chem. Soc. Perkin Trans. 1, 1194-12009
10. Eliel, E.L., Wilen, S.H. & Mander, L.N. (1994) Stereochemistry of Organic Compounds, ch. 7, John Wiley & Sons, New York
11. Bada, J.L. (1985) in Chemistry and Biochemistry of Amino Acids (Barrett, G.C. ed.), ch. 13, Chapman & Hall, London
12. Williams, K.M. & Smith, G.G. (1977) Origins of Life 8, 91-144
13. Sakakibara, S. & Itoh, M. (1967) Bull. Chem. Soc. Jpn. 40, 656-661
14. Kovacs, J., Cover, R.E., Johnson, R.H., Kalas, T.J., Mayers, G.L. & Roberts, J.E. (1973) J. Org. Chem. 38, 2518-2521
15. Vaughan, Jr., J.R. (1952) J. Am. Chem. Soc. 74, 6137
16. Kovacs, J., Cover, R., Jham, G., Hsieh, Y. & Kalas, T. (1975) in Peptides: Chemistry, Structure, and Biology (Walter, R. & Meienhofer, J., eds.), pp. 317-324, Ann Arbor Science Press, Ann Arbor
17. Abdelmoty, I., Albericio, F., Carpino, L.A., Foxman, B. & Kates, S.A. (1994) Letters in Peptide Science 1, 57-67
18. Castro, B., Dormoy, J.-R., Dourtoglon, B., Erin, G., Selve, C. & Ziegler, J.-C. (1976) Synthesis, 751-752
19. Dourtoglu, V., Ziegler, J.-C. & Gross, B. (1978) Tetrahedron Lett., 1269-1272
20. Coste, J., Frérot, E. & Jouin, P. (1994) J. Org. Chem. 59, 2437-2446
21. Carpino, L.A. (1993) J. Am. Chem. Soc. 115, 4397-4398
22. Carpino, L.A. & El-Faham, A. (1995) J. Am. Chem. Soc. 117, 5401-5402
23. Angell, Y.M., García-Echeverria, C. & Rich, D.H. (1994) Tetrahedron Lett. 35, 5981-5984
24. Anderson, G.W., Zimmerman, J.E. & Callahan, F.M. (1966) J. Am. Chem. Soc. 88, 1338 1339
25. Smart, N.A., Young, G.T. & Williams, M.W. (1960) J. Chem. Soc., 3902-3912
26. Carpino, L.A., Mansour, E.-M.E. & Sadat-Aalaee (1991) J. Org. Chem. 56, 2611-2614