Solid-Phase Synthesis of [2-Isoleucine,4-leucine]oxytocin and [2-Phenylalanine,4-leucine] oxytocin and Some of Their Pharmacological Properties

Journal of Medicinal Chemistry

Volumn 16, Issue 6, 1973, Pages 624-629

  Hruby, Victor J ^a   Mustio, Fugen ^a   Groginsky, Charles M ^a   Gitu, Peter M ^a   Saba, Don ^a   Chan, Walter Y ^b  

^a UNIVERSITY OF ARIZONA   (United States)

^b WEILL CORNELL MEDICAL COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CALCIUM; IMIDE; ISOLEUCINE; LEUCINE; OXYTOCIN; PEPTIDE; PHENYLALANINE;

ANIMAL; ARTICLE; DIURESIS; DRUG EFFECT; FEMALE; GEL CHROMATOGRAPHY; HYDROLYSIS; IN VITRO STUDY; PHOTOMETRY; RAT; SYNTHESIS; TECHNIQUE; THIN LAYER CHROMATOGRAPHY; UTERUS;

ANIMAL; CALCIUM; CHROMATOGRAPHY, GEL; CHROMATOGRAPHY, THIN LAYER; DIURESIS; FEMALE; HYDROLYSIS; IMIDES; IN VITRO; ISOLEUCINE; LEUCINE; METHODS; OXYTOCIN; PEPTIDES; PHENYLALANINE; PHOTOMETRY; RATS; UTERUS;

EID: 0015633979     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm00264a010     Document Type: Article

References (53)

1. J. Rudinger and I. KrejCi in “Handbook of Experimental Pharmacology,” Vol. 23, B. Berde, Ed., Springer-Verlag, Berlin, 1968, p 748.
2. W. Y. Chan, V. J. Hruby, G. Flouret, and V. du Vigneaud, Science, 161, 280 (1968).
3. V. J. Hruby, G. Flouret, and V. du Vigneaud, J. Biol. Chem., 244, 3890 (1969).
4. W. Y. Chan and V. du Vigneaud, J. Pharmacol. Exp. Ther., 174, 541 (1970).
5. P. J. S. Chiu and W. H. Sawyer, Amer. J. Physiol., 218, 838 (1970).
6. H. Datta and R. R. Chaudhury, J. Endocrinol., 46, 117 (1970).
7. H. Datta and R. R. Chaudhury, J. Endocrinol., 42, 345 (1968).
8. V. J. Hruby and W. Y. Chan, J. Med. Chem., 14, 1050 (1970).
9. V. J. Hruby, V. du Vigneaud, and W. Y. Chan, J. Med. Chem., 13, 185 (1970).
10. M. A. Wille, V. du Vigneaud, and W. Y. Chan, J. Med. Chem., 15, 11 (1972).
11. J. Rudinger, O. V. Kaserer, K. Poduska, B. T. Pickering, R. E. J. Dyball, D. R. Ferguson, and W. R. Ward, Experientia, 25, 680 (1969).
12. P. G. Pietta and G. R. Marshall, Chem. Commun., 650 (1970).
13. R. B. Merrifield, J. Amer. Chem. Soc, 85, 2149 (1963).
14. R. B. Merrifield, Advan. Enzymol., 32, 221 (1969).
15. D. H. Spackman, W. H. Stein, and S. Moore, Anal. Chem., 30, 1190(1958).
16. E. Schnabel, JustusLiebigsAnn. Chem., 702, 188 (1967).
17. V. J. Hruby, L. E. Barstow, and T. Linhart, Anal. Chem., 44, 343 (1972).
18. E. Kaiser, R. L. Colescott, C. D. Bossinger, and P. I. Cook, Anal. Biochem., 34, 505 (1970).
19. K. W. Ehler, Ph.D. Dissertation, University of Arizona, 1972.
20. K. Esko, S. Karlsson, and J. Porath, Acta Chem. Scand., 22, 3342 (1968).
21. L. E. Barstow and V. J. Hruby, Macromoi. Syn., 4, 91 (1972).
22. O. H. Lowry, N. J. Rosebrough, A. L. Farr, and R. J. Randall, J. Biol. Chem., 193, 265 (1951).
23. D. Yamashiro, Nature (London), 201, 76 (1964).
24. D. Yamashiro, D. Gillessen, and V. du Vigneaud, J. Amer. Chem. Soc, 88,1310 (1966).
25. J. Porath and P. Flodin, Nature (London), 183, 1657 (1959).
26. H. Takashima, V. J. Hruby, and V. du Vigneaud, J. Amer. Chem. Soc, 92, 677 (1970).
27. J. M. Stewart and J. D. Young, “Solid Phase Peptide Synthesis,” W. H. Freeman, San Francisco, Calif., 1969, p 32.
28. S. Moore and W. H. Stein, Methods Enzymol., 6, 819 (1963).
29. L. A. Branda, V. J. Hruby, and V. du Vigneaud, Mol. Pharmacol, 3, 248 (1967).
30. P. Holton, Brit. J. Pharmacol., 3, 328 (1948).
31. R. A. Munsick, Endocrinology, 66, 451 (1960).
32. “The Pharmacopeia of the United States of America,” 17th review, Mack Publishing Co., Easton, Pa., 1965, p 749.
33. W. A. Jeffers, M. M. Livezy, and J. H. Austin, Proc. Soc. Exp. Biol. Med., 50, 184 (1942).
34. W. H. Sawyer, Endocrinology, 63, 694 (1958).
35. L. D. Markley and L. C. Dorman, Tetrahedron Lett., 1787 (1970).
36. D. T. Gish, P. G. Katsoyannis, G. P. Hess, and R. J. Stedman, J. Amer. Chem. Soc., 78, 5954 (1956).
37. C. Ressler, J. Amer. Chem. Soc., 78, 5959 (1956).
38. D. V. Kashelikar and C. Ressler, J. Amer. Chem. Soc., 86, 2467 (1964).
39. H. Takashima, V. du Vigneaud, and R. B. Merrifield, J. Amer. Chem. Soc., 90, 1323 (1968).
40. B. Gutte and R. B. Merrifield, J. Biol. Chem., 246, 1922 (1971).
41. D. Theodoropoulos and I. Souchleris, Acta Chim. Acad. Sci. Hung., 44, 183 (1965).
42. E. Schnabel, H. Klostermeyer, J. Dahlmans, and H. Zahn, Justus Liebigs Ann. Chem., 707, 227 (1967).
43. A. B. Robinson, J. H. McKerrow, and P. day, Proc. Nat. Acad. Sci. U. S., 66, 753 (1970).
44. F. Weygand, W. Steglich, J. Bjarnason, R. Akhtar, and N. Chytil, Chem. Ber., 101, 3623 (1968).
45. F. Weygand, W. Steglich, and J. Bjarnason, Chem. Ber., 101, 3642 (1968).
46. P. G. Pietta, P. Cavallo, and G. R. Marshall, J. Org. Chem., 36, 3966 (1971).
47. S. Sakakibara, M. Shin, M. Fujino, Y. Shimanishi, S. Inoue, and N. Inukai, Bull. Chem. Soc. Jap., 38, 1522 (1965).
48. J. Lenard and A. B. Robinson, J. Amer. Chem. Soc, 89, 181 (1967).
49. D. B. Hope, V. V. S. Murti, and V. du Vigneaud, J. Biol. Chem., 237, 1563 (1962).
50. M. Manning, J. Amer Chem. Soc, 90, 1348 (1968).
51. W. Konig and R. Geiger, Chem. Ber., 103, 788 (1970).
52. R. Walter, M. A. Kirchberger, and V. J. Hruby, Experientia, 28, 959 (1972).
53. H. P. Bar, O. Hechter, I. L. Schwartz, and R. Walter, Proc. Nat. Acad. Sci. U. S., 67, 7 (1970).