A new approach to conformationally restricted peptide analogs: Rigid β-bends. 1. Enkephalin as an example

作者: John L. Krstenansky , Robert L. Baranowski , Bruce L. Currie

DOI: 10.1016/0006-291X(82)91928-3

关键词:

摘要: Abstract A means of producing a peptide analogue that is permanently fixed in β-bend conformation has been devised. These analogues are based on appropriately substituted derivatives the ring system, 5H-6-oxo-2,3,4,4a,7,7a-hexahydropyrano [2,3,-b]pyrrole. The substituents chosen to represent relevant side chains amino acids. first this type enkephalin synthesized and was found have same order magnitude activity guinea pig ileum assay as morphine.

参考文章(21)
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
C. Garbay-Jaureguiberry, B.P. Roques, R. Oberlin, 1H and 13C NMR studies of conformational behaviour of Leu-enkephalin FEBS Letters. ,vol. 76, pp. 93- 98 ,(1977) , 10.1016/0014-5793(77)80128-2
S. Premilat, B. Maigret, Conformations of Angiotensin II and Enkephalin related to N.M.R Biochemical and Biophysical Research Communications. ,vol. 91, pp. 534- 539 ,(1979) , 10.1016/0006-291X(79)91555-9
C. Garbay-Jaureguiberry, B.P. Roques, R. Oberlin, M. Anteunis, A.K. Lala, Preferential conformation of the endogenous opiate-like pentapeptide met-enkephalin in DMSO-d6 solution determined by high field 1H NMR Biochemical and Biophysical Research Communications. ,vol. 71, pp. 558- 565 ,(1976) , 10.1016/0006-291X(76)90823-8
WILLIAM A. GIBBONS, VICTOR GARSKY, CLAUDE R. JONES, Proton magnetic resonance studies of conformation and flexibility of enkephalin peptides. Nature. ,vol. 262, pp. 779- 782 ,(1976) , 10.1038/262779A0
M.A. Khaled, M.M. Long, W.D. Thompson, R.J. Bradley, G.B. Brown, D.W. Urry, Conformational states of enkephalins in solution. Biochemical and Biophysical Research Communications. ,vol. 76, pp. 224- 231 ,(1977) , 10.1016/0006-291X(77)90715-X
Peter W. Schiller, Bernhard Eggimann, John DiMaio, Carole Lemieux, Thi M.-D. Nguyen, Cyclic enkephalin analogs containing a cystine bridge Biochemical and Biophysical Research Communications. ,vol. 101, pp. 337- 343 ,(1981) , 10.1016/0006-291X(81)91265-1
Frank A. Momany, Conformational analysis of methionine-enkephalin and some analogs. Biochemical and Biophysical Research Communications. ,vol. 75, pp. 1098- 1103 ,(1977) , 10.1016/0006-291X(77)91495-4