Conformational investigation of α,β-dehydropeptides. IX. N-acetyl- (E)-α,β-dehydrobutyrine N'-methylamide: Stereoelectronic properties from infrared and theoretical studies

Journal of Peptide Research

Volumn 52, Issue 1, 1998, Pages 72-79

  Broda, M A ^a   Rzeszotarska, B ^a   Smelka L ^a   Pietrzynski G ^a  

^a UNIVERSITY OF OPOLE   (Poland)

Author keywords

(E) , dehydrobutyrine; Amidic resonance; C5 conformation; C5 hydrogen bond; Density functionals; FTIR spectroscopy; Molecular orbital method; Solution peptide conformation; , dehydroamino acids

Indexed keywords

PEPTIDE DERIVATIVE;

ANALYTIC METHOD; ARTICLE; BINDING AFFINITY; CARBOXY TERMINAL SEQUENCE; CONFORMATIONAL TRANSITION; DRUG RECEPTOR BINDING; FOURIER TRANSFORMATION; HYDROGEN BOND; INFRARED SPECTROSCOPY; NONHUMAN; PEPTIDE SYNTHESIS; PRIORITY JOURNAL; PROTEIN CONFORMATION;

EID: 0031824557     PISSN: 1397002X     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1399-3011.1998.tb00654.x     Document Type: Article

References (62)

1. Broda, M.A., Rzeszotarska, B., Smełka, L. & Rospenk, M. (1997) J. Pept. Res. 50, 341-351.
2. Pietrzyński, G. & Rzeszotarska, B. (1995) in 2nd Israeli-Polish Symposium on the Chemistry and Biology of Peptides and Proteins, Rehovot, Israel, 4-11 April 1995, Rehovot. Program and Abstracts, p. 55.
3. Broda, M.A. & Rzeszotarska, B. (1997) in 3rd Polish-Israeli Symposium. Peptides and Proteins: from Basic Chemistry to Medical Applications, Warsaw, Poland, 19-25 May 1997, Warsaw. Program and Abstracts, p. 9.
4. Hruby, V.J., Al-Obeidi, F. & Kaźmierski, W. (1990) Biochem. J. 268, 249-262.
5. Hruby, V.J. (1993) Biopolymers 33, 1073-1082.
6. Marshall, G.R. (1993) Tetrahedron 49, 3547-3558.
7. Hruby, V.J. (1994) in Peptides: Chemistry, Structure and Biology. Proc. 13th Am. Pept. Symp., 1993 (Hodges, R.S. & Smith, J.A., eds.) pp. 3-17, Escom, Leiden.
8. Pietrzyński, G. & Rzeszotarska, B. (1995) Pol. J. Chem. 69, 1595-1614 and references cited therein.
9. Jain, R. & Chauhan, V.S. (1996) Biopolymers (Pept. Sci.) 40, 105-119 and references cited therein.
10. Benedetti, E. (1996) Biopolymers (Pept. Sci.) 40, 3-44.
11. Karle, I.L. (1996) Biopolymers (Pept. Sci.) 40, 157-180.
12. Nitz, T.J., Shimohigashi, Y., Costa, T., Chen, H-Ch. & Stammer, Ch.H. (1986) Int. J. Pept. Protein Res. 27, 522-529.
13. Mosberg, H.I., Dua, R.K., Pogozheva, I.D. & Lomize, A.L. (1996) Biopolymers 39, 287-296.
14. Edvards, J.W., Fanger, B.O., Cashman, E.A., Eaton, S.R. & McLean, L.R. (1992) in Peptides: Chemistry and Biology. Proc. 12th Am. Pept. Symp., 1991 (Smith, J.A, & Rivier, J.E., eds.) pp. 52-53, Escom, Leiden.
15. Edwards, J.W. & Fanger, B.O. (1993) Patent WO 16,105
16. Vleggaar, R. & Wessels, P.L. (1980) J. Chem. Soc., Chem. Commun. 160-162.
17. Kleinkauf, H. & von Döhren, H. (1990) in Biochemistry of Peptide Antibiotics (Kleinkauf, H. & von Döhren, H., eds.) pp. 1-31, Walter de Gruyter, Berlin, and references cited therein.
18. Nakamura, Y., Ito, A. & Shin, Ch. (1984) Bull. Chem. Soc. Jpn. 67, 2151-2561.
19. 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.
20. Pedras, M.S.C., Taylor, J.T. & Nakashima, T.T. (1993) J. Org. Chem. 58, 4778-4480.
21. Ward, D.E., Vazquez, A. & Pedras, M.S.C. (1996) J. Org. Chem. 61, 8008-8009.
22. Bennet, A.J., Somayaji, V., Brown, R.S. & Santarsiero, B.D. (1991) J. Am. Chem. Soc. 113, 7563-7571.
23. Nitz, T.J., Holt, E.M., Rubin, B. & Stammer, Ch.H. (1981) J. Org. Chem. 46, 2667-2671.
24. Kubica, Z., Rzeszotarska, B., Makowski, M., Główka, M.L. & Gałdecki, Z. (1988) Pol. J. Chem. 62, 107-113.
25. Easton, C.J., Hutton, C.A., Roselt, P.D. & Tiekink, E.R.T. (1991) Aust. J. Chem. 44, 687-694.
26. Smetłka, L., Rzeszotarska, B., Broda, M.A. & Kubica, Z. (1997) Org. Prep. Proc. Int. 29, 696-701.
27. GRAMS/386 Version 3.01B (1994) Galactic Industries Corp., Salem, NH.
28. Devar, M.J.S., Zoebisch, E.G., Healy, E.F. & Stewart, J.J.P. (1985) J. Am. Chem. Soc. 107, 3902-3909.
29. Petersson, G.A. & Al-Laham, M.A. (1991) J. Chem. Phys. 94, 6081-6090.
30. Lee, C., Yang, W. & Parr, R.G. (1988) Phys. Rev. B: Condens. Matter 37, 785-789.
31. Becke, A.D. (1993) J. Chem. Phys. 98, 5648-5652.
32. Peng, C.Y., Ayala, P.Y., Schlegel, H.B. & Frisch, M.J. (1996) J. Comput. Chem. 17, 49-56.
33. Stewart, J.J.P. (1990) J. Comput.-Aided Mol. Des. 4, 1-105.
34. Frisch, M.J., Trucks, G.W., Schlegel, H.B., Gill, P.M.W., Johnson, B.G., Robb, M.A., Cheeseman, J.R., Keith, T.A., Petersson, G.A., Montgomery, J.A., Raghavachari, K., Al-Laham, M.A., Zakrzewski, V.G., Ortiz, J.V., Foresman, J.B., Cioslowski, J., Stefanov, B.B., Nanayakkara, A., Challacombe, M., Peng, C.Y., Ayala, P.Y., Chen, W., Wong, M.W., Andres, J.L., Replogle, E.S., Gomperts, R., Martin, R.L., Fox, D.J., Binkley, J.S., DeFrees, D.J., Baker, J., Stewart, J.J.P, Head-Gordon, M., Gonzalez, C. & Pople, J.A. (1995) GAUSSIAN 94, Revision C.3, Gaussian, Inc., Pittsburgh PA.
35. Parmentier, J., De Wael, K. & Zeegers-Huyskens, Th. (1992) J. Mol. Struct. 270, 217-227.
36. Boussard, G., Marraud, M. & Néel, J. (1974) J. Chim. Phys. Phys.-Chim. Biol. 71, 1081-1091.
37. Boussard, G., Marraud, M. & Aubry, A. (1979) Biopolymers 18, 1297-1331.
38. Shaw, R.A., Kollát, E., Hollósi, M. & Mantsch, H.H. (1995) Spectrochim. Acta A 51, 1399-1412 and references cited therein.
39. Miyazawa, M., Kyogoku, Y. & Sugeta, H. (1994) Spectrochim. Acta A 50, 1505-1511 and references cited therein.
40. Néel, J. (1972) Pure Appl. Chem. 31, 201-225.
41. Mizuno, K., Nishio, S. & Shindo, Y. (1979) Biopolymers 18, 693-708.
42. Maxfield, F.R., Leach, S.J., Stimson, E.R., Powers, S.P. & Scheraga, H.A. (1979) Biopolymeis 18, 2507-2521.
43. Maxfield, F.R., Bandekar, J., Krimm, S., Evans, D.J., Leach, S.J., Némethy, G. & Scheraga, H.A. (1981) Macromolecules 14, 997-1003.
44. Cheam, T.C. & Krimm, S. (1989) J. Mol. Struct. 193, 1-34; (1989) J. Mol. Struct. (Theochem) 188, 15-43; (1990) J. Mol. Struct. (Theochem) 206, 173-203.
45. Cheam, T.C. & Krimm, S. (1989) J. Mol. Struct. 193, 1-34; (1989) J. Mol. Struct. (Theochem) 188, 15-43; (1990) J. Mol. Struct. (Theochem) 206, 173-203.
46. Cheam, T.C. & Krimm, S. (1989) J. Mol. Struct. 193, 1-34; (1989) J. Mol. Struct. (Theochem) 188, 15-43; (1990) J. Mol. Struct. (Theochem) 206, 173-203.
47. Grenie, Y., Avignon, M. & Garrigou-Lagrange C. (1975) J. Mol. Struct. 14, 293-307.
48. Permentier, J., Samyn, C., Van Beylen, M. & Zeegers-Huyskens, Th. (1991) J. Chem. Soc. Perkin Trans. 2 387-392.
49. Shaw, R.A., Perczel, A., Fasman, G.D. & Mantsch, H.H. (1996) Int. J. Pept. Protein Res. 48, 71-78.
50. Kulbida, A., Ramos, M.N., Rasanen, M., Nieminen, J., Schrems, O. & Fausto, R. (1995) J. Chem. Soc. Faraday Trans. 91, 1571-1585.
51. Deng, Z., Polavarapu, P.L., Ford, S.J., Hecht, L., Barron, L.D., Ewig, C.S. & Jalkanen, K. (1996) J. Phys. Chem. 100, 2025-2034.
52. Gould, I.R., Cornell, W.D. & Hillier, I.H. (1994) J. Am. Chem. Soc. 116, 9250-9256.
53. Latajka, Z. & Bouteiller, Y. (1994) J. Chem. Phys. 101, 9793-9799.
54. Adamo, C., Dillet, V. & Barone, V. (1996) Chem. Phys. Lett. 263, 113-118 and references cited therein.
55. Ziegler, T. (1991) Chem. Rev. 91, 651-667.
56. Stephens, P.J., Devlin, F.J., Chabalowski, C.F. & Frisch, M.J. (1994) J. Phys. Chem. 98, 11623-11627.
57. Gupta, A. & Chauhan, V.S. (1993) Int. J. Pept. Protein Res. 41, 421-426.
58. Pietrzyński, G., Rzeszotarska, B. & Kubica, Z. (1992) Int. J. Pept. Protein Res. 40, 524-531.
59. Pietrzyński, G., Rzeszotarska, B., Ciszak, E. & Lisowski, M. (1994) Pol. J. Chem. 68, 1015-1021.
60. Pietrzyński, G., Rzeszotarska, B., Ciszak, E., Lisowski, M., Kubica, Z. & Boussard, G. (1996) Int. J. Pept. Protein Res. 48, 347-356.
61. Taylor, P., Mikol, V., Kalle, J., Burkhard, P. & Walkinshaw, M.D. (1996) Biopolymers (Pept. Sci.) 40, 585-592.
62. Müller, G. (1996) Angew. Chem. Int. Ed. Engl. 35, 2767-2769.