volume 31 issue 2 pages 109-115

Conformation of D-Phe-Cys-Tyr-D-Trp-Lys-Thr-Pen-Thr-NH2 (CTP-NH2), a highly selective mu-opioid antagonist peptide, by 1H and 13C n.m.r.

JOHN T. PELTON 1
Michael Whalon 2
Wayne L. Cody 3
Victor J. Hruby 3
1
 
Merrell Dow Research Institute, Indianapolis, Indiana.
2
 
Merrell Dow Research Institute, Indianapolis, Indiana, USA
Publication typeJournal Article
Publication date2009-01-12
SJR
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ISSN03678377
Biochemistry
Abstract
The 1H and 13C n.m.r. spectral parameters of CTP-NH2 [D-Phe-Cys-Tyr-D-Trp-Lys-Thr-Pen-Thr-NH2], a potent, highly selective mu-opiate antagonist, were measured in aqueous solution and a possible conformation has been deduced from the spectral data. The data are consistent with a type II' beta-turn for the tetrapeptide sequence -Tyr3-D-Trp4-Lys5-Thr6-. Solvent shielding of the Cys2 amide proton, observed in variable temperature experiments, suggests an orientation of this amide proton toward the gem dimethyls of Pen7 with possible hydrogen bonding to the Thr6 carbonyl oxygen, and a dihedral angle of -110 degrees for the disulfide bond. Partially relaxed Fourier transform 13C relaxation studies confirm a constrained cyclic system, with the C alpha carbons in the "hinge" of the beta-turn having the shortest t1 times. Segmental motion was observed for the side chain of Lys5.
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PELTON J. T. et al. Conformation of D-Phe-Cys-Tyr-D-Trp-Lys-Thr-Pen-Thr-NH2 (CTP-NH2), a highly selective mu-opioid antagonist peptide, by 1H and 13C n.m.r. // International journal of peptide & protein research. 2009. Vol. 31. No. 2. pp. 109-115.
GOST all authors (up to 50) Copy
PELTON J. T., Whalon M., Cody W. L., Hruby V. J. Conformation of D-Phe-Cys-Tyr-D-Trp-Lys-Thr-Pen-Thr-NH2 (CTP-NH2), a highly selective mu-opioid antagonist peptide, by 1H and 13C n.m.r. // International journal of peptide & protein research. 2009. Vol. 31. No. 2. pp. 109-115.
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TY - JOUR
DO - 10.1111/j.1399-3011.1988.tb00012.x
UR - https://doi.org/10.1111/j.1399-3011.1988.tb00012.x
TI - Conformation of D-Phe-Cys-Tyr-D-Trp-Lys-Thr-Pen-Thr-NH2 (CTP-NH2), a highly selective mu-opioid antagonist peptide, by 1H and 13C n.m.r.
T2 - International journal of peptide & protein research
AU - PELTON, JOHN T.
AU - Whalon, Michael
AU - Cody, Wayne L.
AU - Hruby, Victor J.
PY - 2009
DA - 2009/01/12
PB - Wiley
SP - 109-115
IS - 2
VL - 31
PMID - 2896638
SN - 0367-8377
ER -
BibTex |
Cite this
BibTex (up to 50 authors) Copy
@article{2009_PELTON,
author = {JOHN T. PELTON and Michael Whalon and Wayne L. Cody and Victor J. Hruby},
title = {Conformation of D-Phe-Cys-Tyr-D-Trp-Lys-Thr-Pen-Thr-NH2 (CTP-NH2), a highly selective mu-opioid antagonist peptide, by 1H and 13C n.m.r.},
journal = {International journal of peptide & protein research},
year = {2009},
volume = {31},
publisher = {Wiley},
month = {jan},
url = {https://doi.org/10.1111/j.1399-3011.1988.tb00012.x},
number = {2},
pages = {109--115},
doi = {10.1111/j.1399-3011.1988.tb00012.x}
}
MLA
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MLA Copy
PELTON, JOHN T., et al. “Conformation of D-Phe-Cys-Tyr-D-Trp-Lys-Thr-Pen-Thr-NH2 (CTP-NH2), a highly selective mu-opioid antagonist peptide, by 1H and 13C n.m.r..” International journal of peptide & protein research, vol. 31, no. 2, Jan. 2009, pp. 109-115. https://doi.org/10.1111/j.1399-3011.1988.tb00012.x.