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Conformational studies of stereoisomeric 14-membered cyclic enkephalin analogues containing 1-naphthyialanine at the fourth position: Chirality effect of leucine at the fifth position on biological activity and receptor selectivity by Toshimasa Yamazaki; Odile E. Said-Nejad; Peter W. Schiller; Murray Goodman is a Biochemistry, Genetics and Molecular Biology article available to read on EtoBox.

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In order to study structure-activity relationships of enkephalin-related analogues, we report the biological activity and conformational analysis of four 14-membered cyclic enkephalin analogues with P-( 1-naphthy1)alanine in place of phenylalanine a t the fourth position, Tyr-c [ D-A,bu-Gly-( L and D ) -PNal( 1) -( L and D ) -Leu]. The L-PNal( 1 ) -containing analogues display higher activity at both the p and 6 receptors than the corresponding analogues with the L-Phe residue. In contrast to the linear enkephalins, the cyclic analogues with the D-PNal( 1 ) residue are also active at the p receptor since the relative spatial arrangement of functional groups required for biological activity is achieved by the constrained nature of the cyclic molecules. A comparison of the findings from the conformational analysis and biological assays establishes that relatively extended structures, in which the two aromatic side chains are oriented in opposite directions with a -14 8, separation, is required for activity at the p receptor. On the other hand, folded conformations with nearly parallel orientations and a close proximity ( < lOA) of the aromatic rings of the Tyr and pNal( 1) residues a

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Author

Toshimasa Yamazaki; Odile E. Said-Nejad; Peter W. Schiller; Murray Goodman

Publisher

Wiley (John Wiley & Sons); John Wiley & Sons Inc.; Wiley (ISSN 0006-3525)

Published

1991

Language

EN

Field

Biochemistry, Genetics and Molecular Biology (Life Sciences)