ISSN:
0006-3525
Keywords:
Chemistry
;
Polymer and Materials Science
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
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.
Additional Material:
3 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/bip.360260909
