Synthesis,Characterization, and Biological Properties of Five Enkephalin-like Pentapeptides Containing p-Nitrophenylalanine |
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Authors: | Jean-Luc Fauch re,Peter W. Schiller |
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Affiliation: | Jean-Luc Fauchère,Peter W. Schiller |
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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. |
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