Conformational studies of diastereomeric cyclic enkephalins by 1H-NMR and computer simulations

We report the solid‐phase synthesis and conformational analysis of a 14‐membered, cyclic enkephalin analog, HTyrc[DA2buGlyPheDLeu] (where A2bu represents α,γ‐diaminobutyric acid). The results from the guinea pig ileum (GPI) and mouse vas deferens (MVD) assays show that the analog, though ac...

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Veröffentlicht in:Biopolymers 1987-09, Vol.26 (9), p.1573-1586
Hauptverfasser: Mierke, Dale F., Lucietto, Pierluigi, Goodman, Murray, Schiller, Peter W.
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Sprache:eng
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Zusammenfassung:We report the solid‐phase synthesis and conformational analysis of a 14‐membered, cyclic enkephalin analog, HTyrc[DA2buGlyPheDLeu] (where A2bu represents α,γ‐diaminobutyric acid). The results from the guinea pig ileum (GPI) and mouse vas deferens (MVD) assays show that the analog, though active, has little selectivity for the μ or δ opioid receptors. Conformational analysis is carried out using 1H‐nmr and computer simulations, including molecular dynamics and energy minimizations. The results obtained here are compared with the findings of our studies carried out on the μ‐receptor‐selective diastereomer, HTyrc[DA2buGlyPheLeu] [N. Mammi, M. Hassan, and M. Goodman (1985) J. Am. Chem. Soc. 107, 4008–4013]. This comparison allows for insight into the regiospecificity of these cyclic enkephalin analogs.
ISSN:0006-3525
1097-0282
DOI:10.1002/bip.360260909