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Fluorinated analogs of Leu-enkephalin were synthesized by the solution method and the solid-phase method. The synthetic peptides were examined for opioid activities on mouse vas deferens and guinea pig ileum. Among the synthetic peptides,[D-Ala2,Leu(F3)(2R,4S)5]enkephalin and [D-Ala2,Leu(F3)(2S,4R)5]enkephalin exhibited potent opioid activity, and [Leu(F3)(2S,4R)5]enkephalin exhibited high delta-receptor selectivity.

Amino Acids and Peptides. XXIII. Leu-Enkephalin Analogs Containing a Fluorinated Amino Acid at Position 2, 4 or 5.