In order to elucidate the contribution of the N-terminal moiety (Phe1 or Met2) of FMRFamide to the activity, 16 kinds of FMRFamide analogs were synthesized and their structure-activity relations are discussed. From the results, it was found that hydrophobic or bulky group in N-terminal contributes to the contractile effect, while the precise length of the side chain of amino acid at 2-position is due to a relaxing effect.
In order to investigate the role of C-terminal Phe4–NH2 of FMRFamide (Phe–Met–Arg–Phe–NH2) to the biological activity, 30 kinds of cyclohexylamide derivatives of peptides related to FMRFamide were synthesized and their FMRFamide-like activity was measured. From the results, it was found that the peptide which was placed at C-terminal Phe4–NH2 by d-Ala–CHA showed only a relaxing activity. Furthermore, it was recognized that Met–Arg–Asp–diCHA inhibited FMRFamide contraction selectively.
309ChemInform Abstract The peptide (I), prepared by the title method, has different effects on molluscan muscles. Depending on the concentration relaxation or contraction is achieved.
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