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- Title
Synthesis, Characterization, and Biological Properties of Five Enkephalin-like Pentapeptides Containing p-Nitrophenylalanine.
- Authors
Fauchère, Jean-Luc; Schiller, Peter W.
- 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-NH2, and Met-NH2 (X = Neo-NH2 is particularly potent) are discussed in terms of hydrophobic and steric factors, and resistance towards enzymic degradation.
- Publication
Helvetica Chimica Acta, 1981, Vol 64, Issue 7, p2090
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.19810640714