title: Synthesis of alpha-MSH fragments containing phenylalanine mustard for receptor studies.
abstract: For chemical affinity labeling of the melanotropin receptor several alpha-MSH fragments containing phenylalanine mustard were synthesized in solution. Tested in the frog skin bioassay the derivatives roughly preserved the biological activity of the corresponding natural sequences. Alkylating peptides with prolonged biological activity containing phenylalanine mustard in place of arginine, phenylalanine or methionine are inhibitors of alpha melanotropin, suggesting an irreversible binding to reactive nucleophiles on the part of the MSH receptor, where the Met-Glu-His-Phe-Arg sequence is attached.
authors.affiliation: Research Group for Peptide Chemistry, Hungarian Academy of Sciences, Budapest.
authors.forename: H
authors.initials: H
authors.lastname: Süli-Vargha
authors.forename: J
authors.initials: J
authors.lastname: Botyánszki
authors.forename: H
authors.initials: H
authors.lastname: Medzihradszky-Schweiger
authors.forename: K
authors.initials: K
authors.lastname: Medzihradszky
mesh_terms: D000345:Affinity Labels / Q000138:chemical synthesis; D000478:Alkylation; D000595:Amino Acid Sequence; D000818:Animals; D066298:In Vitro Techniques; D008558:Melphalan; D008969:Molecular Sequence Data; D010446:Peptide Fragments / Q000138:chemical synthesis* / Q000494:pharmacology; D011895:Rana ridibunda; D011979:Receptors, Pituitary Hormone / Q000187:drug effects; D012867:Skin / Q000187:drug effects; D000521:alpha-MSH / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology
chemical_list: D000345:Affinity Labels; D010446:Peptide Fragments; D011979:Receptors, Pituitary Hormone; D000521:alpha-MSH; C029446:MSH receptor; D008558:Melphalan