Abstract
The synthesis of four enkephalinamide analogs is described in which the peptide bond between residues 4 and 5 is reversed with or without simultaneous reversal of the carboxyl-terminal amide bond.These so-called partially modified retro-inverso-isomers are new, potent, topochemical analogs of the enkephalines.Tests, both in vitro and in vivo, have shown that these analogs are considerably longer acting than any previously studied enkephalins.Thus, partial reversal of the peptide bonds of the backbone can result in peptides with enhanced activity compared to a parent compound, provided that the structural complementary of both the side chains and end groups are conserved.
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