A SOLID PHASE-FRAGMENT APPROACH TO PEPTIDE SYNTHESIS.

The t-alkyloxycarbonylhydrazide-resin, H₂NNHCOOC(CH₃)₂CH₂CH₂-copolystyrene-divinylbenzene, was applied to the solid phase synthesis of a protected decapeptide hydrazide, Z-Ala-Val-Ser(Bzl)-Ile-GIn-Phe-Met(O)-Asn-Leu-NHNH₂, and the t-alkyl alcohol-resin, HO-C(CH₃)₂CH₂CH₂-copolystyrene-divinylbenzene, was applied to the synthesis of Z-Lys(Z)-Phe-Phe-Gly-OH. The protected tetrapeptide was coupled to H-Leu-Met-OCH₃ by a fragment condensation in solution to give the protected hexapeptide, which was converted by ammonolysis and deprotection with hot trifluoroacetic acid to the active analog of eledoisin, H-Lys-Phe-Phe-Gly-Leu-Met-NH₂