International Journal of Peptide and Protein Reseach 1987-03-01

Synthesis and conformational study of a cyclic hexapeptide analogue of somatostatin: cyclo(Phe-D-Trp-Lys-Thr-o-AMPA).

P Vander Elst, E van den Berg, H Pepermans, L vander Auwera, R Zeeuws, D Tourwe, G van Binst

Index: J. Pept. Protein Res. 29 , 464, (1987)

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Abstract

The active sequence Phe7-D-Trp8-Lys9-Thr10 of somatostatin has been cyclized through o-(aminomethyl)phenylacetic acid, a spacer molecule, designed to mimic a Gly-Gly dipeptide containing a cis-constrained peptide bond. The resulting analogue shows no GH-inhibition. A 2D n.m.r. study reveals conformations different from the proposed bio-active one and still sensitive to the medium (solvent).