[Syntheses of oligopeptides related to the insulin sequence B 22-25 (Arg-Gly-Phe-Phe) (author's transl)].
Syntheses of peptides with the sequences Gly-Phe, Gly-Phe-Phe, Arg-Gly-Phe and Arg-Gly-Phe-Phe are described. They were performed with the free acids, methyl esters and caramides. The peptides correspond partially or directly to the insulin sequence B 22 - 25 (Arg-Gly-Phe-Phe), the tetrapeptide amide or tetrapeptide methyl ester of which shows insulin-like activity (l.c.[1,2]). For testing the structural specificity of the arginyl residue, the following peptides were also synthesised: NG-NO2-Arg-Gly-Phe-Phe-NH2 and -OMe, Orn-Gly-Phe-Phe-NH2 and Cit-Gly-Phe-Phe--NH2. In connection with the above, the syntheses of the new derivatives Nalpha,Ndelta-Z2-L-ornithine p-nitrophenyl ester and N-Boc-L-citrulline p-nitrophenyl ester are described. All peptides were synthesised conventionally.
D000595:Amino Acid Sequence; D007328:Insulin / Q000138:chemical synthesis*; D008722:Methods; D009842:Oligopeptides / Q000138:chemical synthesis*; D009904:Optical Rotation
D007328:Insulin; D009842:Oligopeptides
Synthesen von Oligopeptiden mit Beziehung zur Insulinsequenz B 22 - 25 (Arg-Gly-Phe-Phe)