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Oxytocin Analogues Containing No Disulfide Bond. I. Synthesis of the Lactam of L-Tyrosyl-L-isoleucyl-L-glutaminyl-L-asparaginyl-L-α-aminosuberyl-L-prolyl-L-leucylglycine Amide

1969; Oxford University Press; Volume: 42; Issue: 12 Linguagem: Inglês

10.1246/bcsj.42.3491

1348-0634

Akiko Kobayashi, Satoe Hase, Reiko Kiyoi, Shumpei Sakakibara,

Molecular Spectroscopy and Structure

Abstract The synthesis of an analogue of deamino-oxytocin, which has an ethylene linkage in place of the disulfide bond, was studied in order to establish a general route for the synthesis of such cyclic peptides. l-α-Aminosuberic acid (Asu) was converted to the N-benzyloxycarbonyl-ω-t-butyl ester and was used as the starting substance for the synthesis. A protected octapeptide was prepared by the step-by-step elongation method with the respective benzyloxycarbonylamino acid active esters, and finally the cyclization of the ω-carboxyl group of the Asu-residue to the amino group of the tyrosyl-residue was achieved by the trifluoroacetate method. The final product showed obviously higher oxytocin-like activities than those reported previously. The conditions for the syntheses of p-nitrophenyl and 2,4,5-trichlorophenyl trifluoroacetates were improved during the investigation.