Synthesis and conformational study of a cyclic hexapeptide analog of somatostatin containing dehydrophenylalanine
- 1 February 1984
- journal article
- research article
- Published by Wiley in International Journal of Peptide and Protein Research
- Vol. 23 (2) , 212-222
- https://doi.org/10.1111/j.1399-3011.1984.tb02712.x
Abstract
A cyclic hexapeptide analog of somatostatin, cyclo-(Pro-.DELTA.z-Phe-D-Trp-Lys-Thr-Phe) (II) was synthesized by a combination of solid phase and solution methodology. It shows a potency for inhibition of [rat] growth hormone release in vitro .apprx. 1/10 that of the corresponding saturated analog, cyclo-(Pro-Phe-D-Trp-Lys-Thr-Phe) (I). NMR studies indicate comparable backbone conformations for analogs I and II. However, the sum of the 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 NMR studies.Keywords
This publication has 25 references indexed in Scilit:
- Dehydro‐enkephalins: Receptor binding activity of unsaturated analogs of Leu5‐enkephalinFEBS Letters, 1981
- Dehydrophenylalanyl analogs of bradykinin: Synthesis and biological activitiesArchives of Biochemistry and Biophysics, 1981
- A potent cyclic hexapeptide analogue of somatostatinNature, 1981
- Synthesis of dehydrothyroliberin .DELTA.ZPhe-2-TRFThe Journal of Organic Chemistry, 1981
- Opiate activity of [DAla2,ΔzPhe4]-methionine-enkephalinamideBiochemical and Biophysical Research Communications, 1979
- D-Ala2, ΔzPhe4-methionine enkephalin amide, a dehydropeptide hormoneBiochemical and Biophysical Research Communications, 1978
- THE SYNTHESIS OF N‐BENZYLOXYCARBONYL‐L‐PROLYL‐DEHYDROPHENYLALANYL‐L‐HISTIDYL‐L‐LEUCINEInternational Journal of Peptide and Protein Research, 1978
- The enzyme stability of dehydropeptidesBiochemical and Biophysical Research Communications, 1978
- l-3,4-Dehydroproline analogs of bradykininArchives of Biochemistry and Biophysics, 1978
- Pharmacological effects of introducing a double bond into a binding site of oxytocin. Analogs with L-3,4-dehydroproline in position 7Journal of Medicinal Chemistry, 1977