Synthesis and conformational study of two cyclic analogues of somatostatin containing an AMPA‐spacer unit
- 1 March 1987
- journal article
- Published by Wiley in International Journal of Peptide and Protein Research
- Vol. 29 (3), 331-346
- https://doi.org/10.1111/j.1399-3011.1987.tb02260.x
Abstract
Two cyclic somatostatin analogues containing the active sequence Phe7-D-Trp8-Lys9-Thr10 and a meta- or para-(aminomethyl) phenylacetic acid (AMPA) spacer unit, have been synthesized. A conformational study using 2D n.m.r. techniques (COSY, NOESY) reveals that the conformation of the meta-AMPA analogue has some analogy with the bio-active conformation proposed earlier by Veber and colleagues, while in the para-AMPA analogue an equilibrium exists between a beta-II' turn and a gamma-turn structure. Both analogues show no GH-inhibition or LH-inhibition in in vitro assays.Keywords
This publication has 14 references indexed in Scilit:
- SMS 201–995, an octapeptide somatostatin analogue.International Journal of Peptide and Protein Research, 1985
- Hexapeptide analogue of somatostatin, Sandoz 201–456.International Journal of Peptide and Protein Research, 1985
- Homonuclear two‐dimensional correlated spectra with delays as an aid for the assignment of aromatic residues and for sequencing of peptidesBiopolymers, 1984
- Conformational modifications of cyclic hexapeptide somatostatin analogsInternational Journal of Peptide and Protein Research, 1984
- SMS 201–995: A very potent and selective octapeptide analogue of somatostatin with prolonged actionLife Sciences, 1982
- Sequential resonance assignments in protein 1H nuclear magnetic resonance spectraJournal of Molecular Biology, 1982
- Synthesis of analogs of the carboxyl protease inhibitor pepstatin. Effect of structure on inhibition of pepsin and reninJournal of Medicinal Chemistry, 1980
- Secondary Deuterium Isotope Effects on Carbonyl Ylide IntermediatesCanadian Journal of Chemistry, 1975
- The Azide Method in Peptide Synthesis: Its Scope and Limitations1Synthesis, 1974