Proton n.m.r. investigation of conformational influence of penicillamine residues on the disulfide ring system of opioid receptor selective Somatostatin derivatives
- 1 February 1988
- journal article
- research article
- Published by Wiley in International Journal of Peptide and Protein Research
- Vol. 31 (2) , 192-200
- https://doi.org/10.1111/j.1399-3011.1988.tb00022.x
Abstract
Three cyclic disulfide analogs related to somatostatin, D-Phe1- Cys2-Tyr3-D-Trp4-Lys5-Thr6-Xxx7-Thr8NH2 (where Xxx = L-Pen 1; L-Cys 3; or D-pen 4) were examined in DMSO-d6 by one- and two-dimensional proton n.m.r. spectroscopy in order to analyze the conformational influence of the postion-7 residue on the 20-membered disulfide ring. From these studies it was concluded that all three analogs maintain a .beta. II'' turn solution conformation for the core tetrapeptide -Tyr3-D-Trp4-Lys5-Thr6-. However, the disulfide conformation differs in the analogs, with 1 and 3 having a left-handed and 4 a right-handed disulfide chirality.Keywords
This publication has 18 references indexed in Scilit:
- Proton n.m.r. spectroscopic evidence for sulfur‐aromatic interactions in peptidesInternational Journal of Peptide and Protein Research, 1987
- Design and synthesis of conformationally constrained somatostatin analogs with high potency and specificity for .mu. opioid receptorsJournal of Medicinal Chemistry, 1986
- SMS 201–995, an octapeptide somatostatin analogue.International Journal of Peptide and Protein Research, 1985
- SMS 201–995, a very potent analogue of somatostatin. Assignment of the 1H 500 MHz n.m.r. spectra and conformational analysis in aqueous solutionInternational 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
- Application of phase sensitive two-dimensional correlated spectroscopy (COSY) for measurements of 1H-1H spin-spin coupling constants in proteinsBiochemical and Biophysical Research Communications, 1983
- Investigation of complex networks of spin-spin coupling by two-dimensional NMRJournal of Magnetic Resonance (1969), 1981
- NUCLEAR MAGNETIC RESONANCE STUDY ON SOLVENT DEPENDENCE OF SIDE CHAIN CONFORMATIONS OF TYROSINE AND TRYPTOPHAN DERIVATIVESInternational Journal of Peptide and Protein Research, 1981
- A two-dimensional nuclear Overhauser enhancement (2D NOE) experiment for the elucidation of complete proton-proton cross-relaxation networks in biological macromoleculesBiochemical and Biophysical Research Communications, 1980
- Spin—spin coupling and the conformational states of peptide systemsProgress in Nuclear Magnetic Resonance Spectroscopy, 1976