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Synthesis, Characterization, and Biological Properties of Five Enkephalin-like Pentapeptides Containing p-Nitrophenylalanine

✍ Scribed by Jean-Luc Fauchère; Peter W. Schiller

Publisher
John Wiley and Sons
Year
1981
Tongue
German
Weight
314 KB
Volume
64
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

Five pentapeptides with the amino acid sequence L‐tyrosyl‐D‐alanyl‐glycyl‐L‐p‐nitrophenylalanyl‐X, wherein X = L‐leucine, L‐leucine amide, L‐methionine amide, L‐1‐adamantylalanine amide, and L‐neopentylglycine amide were prepared by chemical synthesis in solution and characterized chemically and physically. The effect of the incorporation of the unnatural amino acids adamantylalanine and neopentylglycine, ‘fat’‐analogues of leucine and methionine, on the inhibition of electrically evoked contractions of the myenteric plexus‐longitudinal muscle preparation from guinea pig ileum was studied. Their activities relative to the peptides with X = Leu · OH, Leu‐NH~2~, and Met‐NH~2~ (X = Neo‐NH~2~ is particularly potent) are discussed in terms of hydrophobic and steric factors, and resistance towards enzymic degradation.

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