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Dicarba analogues of the cyclic opioid peptides H-Tyr-c[d-Cys-Gly-Phe-d(or l)-Cys]NH2 were synthesized on solid phase by substituting allylglycines for the cysteines and cyclization by ring-closing metathesis between the side chains of the allylglycine residues. Mixtures of cis and trans isomers of the resulting olefinic peptides were obtained, and catalytic hydrogenation yielded the saturated -CH2-CH2- bridged peptides. The dicarba analogues retained high mu and delta agonist potencies. Remarkably, the trans isomer of H-Tyr-c[d-Allylgly-Gly-Phe-l-Allylgly]NH2 was a mu agonist/delta agonist with subnanomolar potency at both receptors.

journal of medicinal chemistry

Dicarba Analogues of the Cyclic Enkephalin Peptides H-Tyr-<i>c</i>[<scp>d</scp>-Cys-Gly-Phe-<scp>d</scp>(or <scp>l</scp>)-Cys]NH<sub>2</sub> Retain High Opioid Activity

Dicarba Analogues of the Cyclic Enkephalin Peptides H-Tyr-c[d-Cys-Gly-Phe-d(or l)-Cys]NH2 Retain High Opioid Activity

Dicarba Analogues of the Cyclic Enkephalin Peptides H-Tyr-c[d-Cys-Gly-Phe-d(or l)-Cys]NH₂ Retain High Opioid Activity