Synthesis and conformational study of a cyclic hexapeptide analog of somatostatin containing dehydrophenylalanine.

Autor: Brady SF, Cochran DW, Nutt RF, Holly FW, Bennett CD, Paleveda WJ, Curley PE, Arison BH, Saperstein R, Veber DF
Jazyk: angličtina
Zdroj: International journal of peptide and protein research [Int J Pept Protein Res] 1984 Feb; Vol. 23 (2), pp. 212-22.
DOI: 10.1111/j.1399-3011.1984.tb02712.x
Abstrakt: A cyclic hexapeptide analog of somatostatin, cyclo-(Pro-delta z-Phe-D-Trp-Lys-Thr-Phe) (II) has been synthesized by a combination of solid phase and solution methodology. It shows a potency for inhibition of growth hormone release in vitro about one-tenth that of the corresponding saturated analog, cyclo-(Pro-Phe-D-Trp-Lys-Thr-Phe) (I). N.m.r. studies indicate comparable backbone conformations for analogs I and II. However, the sum of our findings from biological evaluation and solution physical data suggest that on the receptor the position-7 phenyl ring of I is adopting a conformation which differs from that of one of the major solution conformers defined previously by n.m.r. studies.
Databáze: MEDLINE