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

✍ Scribed by Dale F. Mierke; Pierluigi Lucietto; Murray Goodman; Peter W. Schiller

Publisher
Wiley (John Wiley & Sons)
Year
1987
Tongue
English
Weight
772 KB
Volume
26
Category
Article
ISSN
0006-3525

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✦ Synopsis

Synopsis

We report the solid-phase synthesis and conformational analysis of a 14-membered, cyclic enkephalin analog, H-Tyr-~$-~-A,bu-Gly-Phe-~-Leu-] (where A,bu represents a,ydiaminobutyric acid). The results from the guinea pig ileum (GPI) and mouse vas deferens (MVD) assays show that the analog, though active, has little seledivity for the p or 8 opioid receptors. Conformational analysis is carried out using 'H-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 p-receptor-selective diastereomer, Chem. SOC. 101,400&4013]. This comparison allows for insight into the regiospecificity of these cyclic enkephalin analogs.

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