Conformational investigation of α,β-dehydropeptides VII. Conformation of Ac-Pro-ΔAla-NHCH3 and Ac-Pro-(E)-ΔAbu-NHCH3: Comparison with (Z)-substituted α,β-dehydropeptides

International Journal of Peptide and Protein Research

Volumn 48, Issue 4, 1996, Pages 347-356

  Pietrzynski G ^a   Rzeszotarska, B ^a   Ciszak, E ^a   Lisowski, M ^a  

^a UNIVERSITY OF OPOLE   (Poland)

Author keywords

C5 conformation; Circular dichroism; Crystal structure; Dehydroalanine; Infrared spectroscopy; Nuclear magnetic resonance; , dehydrobutyrine; , dehydropeptide conformation; lum

Indexed keywords

DEHYDROALANINE;

ARTICLE; CIRCULAR DICHROISM; CRYSTAL STRUCTURE; IN VITRO STUDY; INFRARED SPECTROSCOPY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTEIN STRUCTURE; X RAY DIFFRACTION;

ALANINE; CIRCULAR DICHROISM; DIPEPTIDES; MAGNETIC RESONANCE SPECTROSCOPY; PROLINE; PROTEIN STRUCTURE, SECONDARY; SOLVENTS; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; STEREOISOMERISM; X-RAY DIFFRACTION;

EID: 0029973572     PISSN: 03678377     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1399-3011.1996.tb00851.x     Document Type: Article

References (56)

1. Rzeszotarska, B., Karolak-Wojciechowska, J., Broda, M.A., Galdecki, Z., Trzezwinska, B. & Koziol, A.E. (1994) Int. J. Peptide Protein Res. 44, 313-319
2. Pietrzynski, G., Rzeszotarska, B., Ciszak, E. & Lisowski, M. (1994) Pol. J. Chem. 68, 1014-1021
3. Kleinkauf, H. & von Döhren, H. (1990) in Biochemistry of Feplide Antibiotics (Kleinkauf, H. & von Döhren, H., eds.), pp. 1-31, Walter de Gruyter, Berlin, and references therein
4. Walton, J.D. (1990) in Biochemistry of Peptide Antibiotics (Kleinkauf, H. & von Döhren, H., eds.), pp. 179-203, Walter de Gruyter, Berlin, and references therein
5. Smith, M.J., Kim, D., Horenstein, B. & Nakanishi, K. (1991) Ace. Chem. Res. 24, 117-124 and references therein
6. Jain, R. & Chauhan, V.S. (1996) Biopolymers (Peptide Sci.) 40, 105-119 and references therein
7. Pietrzynski, G. & Rzeszotarska, B. (1995) Pol. J. Chem. 69, 1595-1614 and references therein
8. Pietrzynski, G., Rzeszotarska, B. & Kubica, Z. (1992) Int. J. Peptide Protein Res. 40, 363-370
9. Jung, G. (1991) Augen: Chem., Int. Ed. Engl. 30, 1051-1068 and references therein
10. Noda, K., Shimohigashi, Y. & Izumiya, N. (1983) in The Peptides. Synthesis, Analysis, Biology (Gross, E. & Meienhofer, J., eds.), vol. 5, pp. 285-339, Academic Press, New York and references therein
11. Chan, W.C., Bycroft, B.W., Lian, L.-Y. & Roberts, G.C.K. (1989) FEES Lett. 252, 29-36
12. Shimohigashi, Y., Lee, S., Kato, T. & Izumiya, N. (1978) Bull. Chem. Soc. Jpn. 51, 584-588
13. Mihara, H., Aoyagi, H., Ueno, T., Kato, T. & Izumiya, N. (1986) Bull. Chem. Soc. Jpn. 59, 2041-2043
14. Gavaret, J-M., Nunez, J. & Cahnmann, H.J. (1980) J. Biol. Chem. 255, 5281-5285
15. Shimohigashi, Y. & Stammer, C.H. (1981) Int. J. Peptide Protein Res. 19, 54-62; (1982) Int. J. Peptide Protein Res. 20, 199-206
16. Hallinan, E.A. & Mazur, R.H. (1979) in Peptides. Structure and Biological Function. Proc. 6th Am. Pept. Symp., 1979 (Gross, E. & Meienhofer, J., eds.), pp. 475-77, Pierce Chemical Comp., Rockford, IL
17. Ando, S., Kato, T. & Izumiya, N. (1985) Int. J. Peptide Protein Res. 25, 15-26; Ando, S., Aoyagi, H., Waki, M., Kato, T. & Izumiya, N. (1983) Int. J. Peptide Protein Res. 21,313-321
18. Sharma, A.K. & Chauhan, V.S. (1988) Int. J. Peptide Protein Res. 31, 225-230; Andruszkiewicz, R., Przybylski, J. & Gross, E. (1980) Feder. Proc. 39, 1945
19. Benedetti, E. (1996) Biopolymers (Peptide Sci.) 40, 3-44
20. Vleggaar, R. & Wessels, P.L. (1980) / Chem. Soc., Chem. Commun. 160-162
21. Nakamura, Y., Ito, A. & Shin, C. (1994) Bull. Chem. Soc. Jpn. 67, 2151-2161
22. Culvenor, C.C.J., Edgar, J.A., Mackay, M.F., Gorst-Allman, C.P., Marasas, W.F.O., Steyn, P.S., Vleggaar, R. & Wessels, P.L. (1989) Tetrahedron 45, 2351-2372
23. Rao, Y.S. & Filler, R. (1975) Synthesis 749-764
24. Schmidt, U., Häusler, J., Öhler, E. & Poisel, H. (1979) Prag. Chem. Nat. Prod. 37, 251-327
25. Nitz, T.J., Holt, E.M., Rubin, B. & Stammer, C.H. (1981) J. Org. Chem. 46, 2667-2671
26. Mazur, R.H. & Pilipauskas, D.R. (1981) in Peptides. Synthesis - Structure - Function. Proc. 7th Am Pept. Symp., 19S1 (Rieh, D.H. & Gross, E., eds.), pp. 81-84, Pierce Chemical Company, Rockford, IL
27. Mazur, R.H. & Pilipauskas, D.R. (1983) in Peptides 1982. Proc. 16th Eur. Pept. Symp. (Blâha, K. & Malon, P., eds.), pp. 319-322, Walter de Gruyter, Berlin
28. Shin, C, Ikeda, M. & Yonezawa, Y. (1985) Agric. Biol. Chem., 49, 2243-2245.
29. Makowski, M., Rzeszotarska, B., Kubica, Z., Pietrzynski, G. & Helper, J. (1986) Liebigs Ann. Chem. 980-991
30. Pietrzynski, G. & Rzeszotarska, B. (1991) Bull. Pol. Acad. Sci. Chem. 39, 1-6
31. Kubica, Z., Rzeszotarska, B., Makowski, M., Glöwka, M.L. & Galdecki, Z. (1988) Pol. J. Chem. 62, 107-113
32. Easton, C.J., Hutton, CA., Roselt, P.D. & Tiekink, E.R.T. (1991) Aust. J. Chem. 44, 687-694
33. Gupta, A. & Chauhan, V.S. (1993) Int. J. Peptide Protein Res. 41, 421-426
34. Lisowski, M., Pietrzynski, G. & Rzeszotarska, B. (1993) Int. J. Peptide Protein Res. 42, 466-474
35. Pietrzynski, G., Kubica, Z. & Rzeszotarska, B. (1989) Bull. Pol. Acad. Sci. Chem. 37, 363-370
36. Blessing, R.H. (1989) J. Appl Crystallogr. 22, 396-398
37. Main, P., Hull, S.E., Lessinger, L., Germain, G., Declercq, J.P. & Woolfson, M.M. (1978) MULTAN. A System of Computer Programs for the Automatic Solution of Crystal Structures from X-Ray Diffraction Data. Universities of York, UK and Louvain, Belgium
38. ( 1974) International Tables for X-Ray Crystallography. Vol. IV, Kynoch Press, Birmingham
39. Palmer, D.E., Pattaroni, C., Nunami, K., Chadha, R.K., Goodman, M., Wakamiya, T., Fukase, K., Horimoto, S., Kitazawa, M., Fujita, H., Kubo, A. & Shiba, T. (1992) J. Am. Chem. Soc. 114, 5634-5642
40. Ajô, D., Granozzi, G., Tondello, E., Del Pra, A. & Zanotti, G. (1979) J. Chem. Soc.. Perkin Trans. 2, 927-929
41. Padmanabhan, B., Dey, S., Khandehval, B., Subbra Rao, G. & Singh, T.P. (1992) Biopolymers 32, 1271-1276
42. Piazzesi, A.M., Bardi, R., Crisma, M., Toniolo, C., Singh, M. & Chauhan, V.S. (1993) Z. Kristallogr. 207, 25-32
43. Benedetti, E. (1982) in Chemistry and Biochemistry of Ammo Acids, Peplides and Proteins (Weinstein, B., ed.), vol. 6, pp. 105-184, Marcel Dekker, New York
44. Aubry, A., Pietrzyriski, G., Rzeszotarska, B., Boussard, G. & Marraud, M. (1991) Int. J. Peptidc Protein Res. 37, 37-45
45. Ciszak, E., Pietrzynski, G. & Rzeszotarska, B. (1992) /;;J. J. Peptide Protein Res. 39, 218-222
46. Busetti, V., Crisma, M., Toniolo, C, Salvador!, S. & Balboni, G. (1992) //;J. J. Biol Macromol. 14, 23-28
47. Gupta, A. & Chauhan, V.S. (1990) Biopolymers 30, 395-403
48. Alemän, C. & Casanovas, J. (1995) Biopolymers 36, 71-82
49. Pietrzynski, G. & Rzeszotarska, B. (1995) in Program and Abstracts. Second Israeli-Polish Symposium on the Chemistry and Biology ofPeptides and Proteins, p. 55, Weizmann Institute of Science, Rehovot
50. Jezowska-Bojczuk, M., Kozlowski, H., Sovago, I., Kubica, Z., Rzeszotarska, B. & Smelka, L. (I991) Polyhedron 10, 2331-2335
51. Jezowska-Bojczuk, M., Kozlowski, H., Sovago, I., Kubica, Z., Rzeszotarska, B. & Smelka, L. (1994) Polyhedron 13, 2683-2687
52. Broda, M.A. & Rzeszotarska, B. (1995) in Shaping of \ibrational spectra and molecular interactions. Program and Abstracts of Summer School, P4, Institute of Chemistry, Wroclaw University, Wroclaw
53. Madison, V. & Kopple, K.D. (1980) / Am. Chem. Soc. 102, 4855-4863
54. Siemion, I.Z., Wieland, T. & Pook, K.H. (1975) Angew. Chem. 87, 712-714
55. Singh, M. & Chauhan, V.S. (1994) Proc. Ind. Acad. Sci. Chem. Sci. 106, 1139-1147
56. Singh, T.P. & Narula, P. (1993) Int. J. Peptide Protein Res. 41, 394-398