Conformational features responsible for the binding of cyclic analogues of enkephalin to opioid receptors: II. Models of μ‐ and δ‐receptor‐bound structures for analogues containing Phe4
作者： GREGORY V. NIKIFOROVICH , ALEXANDER A. GOLBRAIKH , MARK D. SHENDEROVICH , JURIS BALODIS
DOI: 10.1111/J.1399-3011.1990.TB00969.X
关键词:
摘要: Models of mu- and delta-receptor-bound backbone conformations enkephalin cyclic analogues containing Phe4 were determined by comparing geometrical similarity among the previously found low-energy structures [D-Cys2,Cys5]-enkephalinamide, [D-Cys2,D-Cys5]-enkephalinamide, [D-Pen2,L-Pen5]-enkephalin [D-Pen2,D-Pen5]-enkephalin. The present mu-receptor-bound conformation resembles a beta-I bend in peptide centred on Gly3-Phe4 region. Two slightly different models for conformation; both them are more extended than include gamma-turn (or gamma-like turn) Gly3 residue. Energetically favourable rotamers Tyr Phe side chains also delta-conformations. delta-conformations share with Leu-enkephalin Tyr-D-Lys-Gly-Phe-analogue.
sci-hub.se 参考文章(20)
Johannes Meienhofer, Murray Goodman, Peptides : proceedings of the 5th American Peptide Symposium Wiley : distributed by Halsted Press. ,(1977)
Parthasarathy Manavalan, Frank A. Momany, Conformational energy calculations on enkephalins and enkephalin analogs. Classification of conformations to different configurational types. International Journal of Peptide and Protein Research. ,vol. 18, pp. 256- 275 ,(2009) , 10.1111/J.1399-3011.1981.TB02980.X
DEREK HUDSON, ROBERT SHARPE, MICHAEL SZELKE, METHIONINE ENKEPHALIN AND ISOSTERIC ANALOGUES International Journal of Peptide and Protein Research. ,vol. 15, pp. 122- 129 ,(2009) , 10.1111/J.1399-3011.1980.TB02558.X
Y. Isogai, G. Nemethy, H. A. Scheraga, Enkephalin: conformational analysis by means of empirical energy calculations. Proceedings of the National Academy of Sciences of the United States of America. ,vol. 74, pp. 414- 418 ,(1977) , 10.1073/PNAS.74.2.414
John DiMaio, Thi M. D. Nguyen, Carole Lemieux, Peter W. Schiller, Synthesis and pharmacological characterization in vitro of cyclic enkephalin analogs: effect of conformational constraints on opiate receptor selectivity Journal of Medicinal Chemistry. ,vol. 25, pp. 1432- 1438 ,(1982) , 10.1021/JM00354A008
John DiMaio, Christopher I. Bayly, G. Villeneuve, Andre Michel, Topological similarities between a cyclic enkephalin analogue and a potent opiate alkaloid: a computer-modeling approach. Journal of Medicinal Chemistry. ,vol. 29, pp. 1658- 1663 ,(1986) , 10.1021/JM00159A016
G.V. Nikiforovich, Conformation—function relationships for peptide bioregulators as revealed by theoretical conformation analysis Journal of Molecular Structure-theochem. ,vol. 134, pp. 325- 340 ,(1986) , 10.1016/0166-1280(86)80005-7
J. Betins, G.V. Nikiforovich, G. Chipens, Statistical weights of Leu-enkephalin conformers in aqueous solution Journal of Molecular Structure: THEOCHEM. ,vol. 137, pp. 129- 132 ,(1986) , 10.1016/0166-1280(86)80091-4
Victor J. Hruby, Lung Fa. Kao, B. Montgomery. Pettitt, Martin. Karplus, The conformational properties of the delta opioid peptide [D-Pen2,D-Pen5]enkephalin in aqueous solution determined by NMR and energy minimization calculations Journal of the American Chemical Society. ,vol. 110, pp. 3351- 3359 ,(1988) , 10.1021/JA00219A002
Peter W. Schiller, Thi M.-D. Nguyen, Louise Maziak, Carole Lemieux, A novel cyclic opioid peptide analog showing high preference for μ-receptors Biochemical and Biophysical Research Communications. ,vol. 127, pp. 558- 564 ,(1985) , 10.1016/S0006-291X(85)80196-0