1H-Pyrazole-1-carboxamidine Hydrochloride: An Attractive Reagent for Guanylation of Amines and Its Application to Peptide Synthesis

Journal of Organic Chemistry

Volumn 57, Issue 8, 1992, Pages 2497-2502

  Bernatowicz, Michael S ^a   Youling, Wu ^a   Matsueda, Gary R ^a  

^a BRISTOL MYERS SQUIBB PHARMACEUTICAL RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33751391460     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00034a059     Document Type: Article

References (31)

1. Fruten, J. S. Adv. Prot. Chem. 1949, 5, 64
2. Bodansky, M. Principles of Peptide Synthesis; Springer-Verlag: New York, 1984; pp 137-141, 192.
3. Rzeszotarska, B.; Masiukiewicz, E. Org. Prep. Proc. Int. 1988, 20, 427.
4. Barany, G.; Merrifield, R. B. In The Peptides; Gross, E., Meienhofer, J., Eds.; Academic Press: New York, 1980; Vol. 2, pp 169-175
5. Fields, G. B.; Nobel, R. L. Int. J. Peptide Protein Res. 1990, 35, 161
6. Bodanszky, M.; Ondetti, M. A.; Birkhimer, C. A.; Thomas, P. L. J. Am. Chem. Soc. 1964, 86, 4452.
7. Borin, G.; Toniolo, C.; Moroder, L.; Marchiori, F.; Rocchi, R.; Scoffone, E. Int. J. Peptide Protein Res. 1972, 4, 37.
8. Gunnar, E.; Lindeberg, G.; Melin, P.; Larsson, L. E. Int. J. Peptide Protein Res. 1976, 8, 193
9. Cosand, W. L.; Merrifield, R. B. Proc. Natl. Acad. Sci. U.S.A. 1977, 74, 2771
10. Granier, C.; Pedroso, E. M.; vanRietschoten, J. Eur. J. Biochem. 1978, 82, 293
11. Davis, T. L. Org. Synth. 1927, 7, 46
12. Kampf, A. Chem. Ber. 1904, 37, 1681.
13. Arndt, F.; Rosenau, B. Chem. Ber. 1917, 50, 1260.
14. Braun, C. E. J. Am. Chem. Soc. 1933, 55, 1280.
15. King, H.; Tonkin, S. M. J. Chem. Soc. 1946, 1063.
16. McKay, A. F.; Hatton, W. G.; Braun, R. O. J. Am. Chem. Soc. 1956, 78, 6144
17. Brand, E.; Brand, F. C. Organic Syntheses; Wiley: New York, 1955; Collect. Vol. III, p 440
18. Jen, T.; Van Hoeven, H.; Groves, W.; McLean, R. A.; Loev, B. J. Med. Chem. 1975, 18, 90.
19. Bannard, R. A. B.; Casselman, A. A.; Cockburn, W. F.; Brown, G. M. Can. J. Chem. 1958, 36, 1541
20. Tian, Z.; Roeske, R. W. Int. J. Peptide Protein Res. 1991, 37, 425
21. Bredereck, H.; Effenberger, F.; Hajek, M. Chem. Ber. 1965, 98, 3178.
22. Wojiechowska, H.; Zgoda, W.; Dziegielewski, K.; Drzewinski, W.; Lutynska, I.; Schoeffer, A.; Borowski, E. Pol. Patent 99496, 15 Nov 1978
23. Miller, A. E.; Bischoff, J. J. Synthesis 1986, 777.
24. Maryanoff, C. A.; Stanzione, R. C.; Plampin, J. M.; Mills, J. E. J. Org. Chem. 1986, 51, 1882.
25. Kim, K.; Lin, Y.-T.; Mosher, H. S. Tetrahedron Lett. 1988, 29, 3183
26. Schenker, E.; Hasspacher, K. U.S. Patent 3,503,984, 31 Mar 1970.
27. Schenker, E.; Hasspacher, K. U.S. Patent 3,519,644, 7 Jul 1970
28. Dryland, A.; Sheppard, R. C. J. Chem. Soc., Perkin Trans. 1 1986, 125.
29. Kaiser, E.; Colescott, R. L.; Bossinger, C. D.; Cook, P. I. Anal. Biochem. 1970, 34, 595
30. Liu, T.-Y.; Boykins, R. A. Anal. Biochem. 1989, 182, 383
31. Brand, E.; Brand, F. C. Organic Syntheses; Wiley: New York, 1955; Collect. Vol. 3, p 440