Conformational study of thyrotrophin-releasing hormone. I. Aspects of importance in the design of novel TRH analogues.

作者: D.J. WARD , E.C. GRIFFITHS , B. ROBSON

DOI: 10.1111/J.1399-3011.1986.TB01043.X

关键词: StereochemistryTripeptideReaction fieldThyrotrophin releasing hormoneCis–trans isomerismMoleculeChemistryReceptor

摘要: The solution conformations of thyrotrophin-releasing hormone (TRH), a biologically-active tripeptide, have been predicted computationally using method which represents effects as dielectric continuum surrounding the molecule throughout energy minimisation; this is described reaction field contribution. compared with previous experimental and theoretical studies. Favoured TRH under other simulated conditions also examined, including behaviour cis isomer, related to possible interactions intermediates specific receptors. relevance these predictions design analogues has analysed.

参考文章(38)
The two conformations of TRH in solution. FEBS Letters. ,vol. 97, pp. 275- 278 ,(1979) , 10.1016/0014-5793(79)80101-5
Suheil F. Abdulnur, R.L. Flurry, J.M. Bopp, Studies of the thyrotropin-releasing hormone I. CNDO/2 studies of the conformations of the residues Journal of Theoretical Biology. ,vol. 59, pp. 189- 203 ,(1976) , 10.1016/S0022-5193(76)80032-X
Ivor M. D. Jackson, Thyrotropin-releasing hormone The New England Journal of Medicine. ,vol. 306, pp. 145- 155 ,(1982) , 10.1056/NEJM198201213060305
P. R. Andrews, D. J. Craik, J. L. Martin, Functional-Group Contributions to Drug Receptor Interactions Journal of Medicinal Chemistry. ,vol. 27, pp. 1648- 1657 ,(1984) , 10.1021/JM00378A021
Maria Liakopoulou-Kyriakides, Richard E. Galardy, s-Cis and s-trans isomerism of the His-Pro peptide bond in angiotensin and thyroliberin analogues. Biochemistry. ,vol. 18, pp. 1952- 1957 ,(1979) , 10.1021/BI00577A016
A. T. Hagler, E. Huler, S. Lifson, Energy functions for peptides and proteins. I. Derivation of a consistent force field including the hydrogen bond from amide crystals. Journal of the American Chemical Society. ,vol. 96, pp. 5319- 5327 ,(1974) , 10.1021/JA00824A004
R. Balasubramanian, A. V. Lakshminarayanan, M. N. Sabesan, G. Tegoni, K. Venkatesan, G. N. Ramachandran, Studies on the conformation of amino acids. VI. Conformation of the proline ring as observed in crystal structures of amino acids and peptides. International Journal of Protein Research. ,vol. 3, pp. 25- 33 ,(2009) , 10.1111/J.1399-3011.1971.TB01689.X
Roxanne Deslauriers, Chantal Garrigou-Lagrange, Anne-Marie Bellocq, Ian C.P. Smith, Carbon-13 nuclear magnetic resonance studies on thyrotropin-releasing factor and related peptides☆ FEBS Letters. ,vol. 31, pp. 59- 66 ,(1973) , 10.1016/0014-5793(73)80073-0