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Comparative conformational analysis of % MathType!MTEF!2!1!+-% feaafeart1ev1aaatCvAUfeBSjuyZL2yd9gzLbvyNv2CaerbuLwBLn% hiov2DGi1BTfMBaeXatLxBI9gBaerbd9wDYLwzYbItLDharqqtubsr% 4rNCHbGeaGqiVu0Je9sqqrpepC0xbbL8F4rqqrFfpeea0xe9Lq-Jc9% vqaqpepm0xbba9pwe9Q8fs0-yqaqpepae9pg0FirpepeKkFr0xfr-x% fr-xb9adbaqaaeGaciGaaiaabeqaamaabaabaaGcbaGaae4waKaaGi% aabseakiaab2cajaaOcaqGqbGcdaqgaaqaaKaaGkaabwgacaqGUbGc% daahaaWcbeqaaiaabkdaaaGccaGGSaqcaaIaaeiraiaab2cajaaOca% qGqbGaaeyzaaWcbaaakiaawYa7aKaaGkaab6gakmaaCaaaleqabaGa% aeynaaaakiaac2faaaa!475D!\[{\text{[D - P}}{\text{n}}^{\text{5}} ]\] enkephalin (DPDPE): A molecular mechanics study

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Summary

A theoretical conformational analysis (molecular mechanics study) of the δ opioid receptor-selective enkephalin analog % MathType!MTEF!2!1!+-% feaafeart1ev1aaatCvAUfeBSjuyZL2yd9gzLbvyNv2CaerbuLwBLn% hiov2DGi1BTfMBaeXatLxBI9gBaerbd9wDYLwzYbItLDharqqtubsr% 4rNCHbGeaGqiVu0Je9sqqrpepC0xbbL8F4rqqrFfpeea0xe9Lq-Jc9% vqaqpepm0xbba9pwe9Q8fs0-yqaqpepae9pg0FirpepeKkFr0xfr-x% fr-xb9adbaqaaeGaciGaaiaabeqaamaabaabaaGcbaGaaeisaiaab2% cacaqGubGaaeyEaiaabkhacaqGTaqcaaIaaeiraiaab2cajaaOcaqG% qbGcdaqgaaqaaKaaGkaabwgacaqGUbGaaeylaiaabEeacaqGSbGaae% yEaiaab2cacaqGqbGaaeiAaiaabwgacaqGTaqcaaIaaeiraiaab2ca% jaaOcaqGqbGaaeyzaaWcbaaakiaawYa7aKaaGkaab6gacaqGTaGaae% 4taiaabIeaaaa!51A0!\[{\text{H - Tyr - D - P}}{\text{n - OH}}\] (DPDPE) was performed, based on the use of the SYBYL software. The study led to the identification of several conformers that were significantly lower in energy than previously reported candidate conformers of DPDPE which, for comparative purposes, were also minimized by using the standard SYBYL force field. The results revealed a considerable degree of conformational flexibility of the DPDPE molecule, and suggested that incorporation of further conformational constraints into this enkephalin analog will be necessary in order to elucidate its receptor-bound conformation.

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Abbreviations

A2bu:

α,γ-diaminobutyric acid

DPDPE:

% MathType!MTEF!2!1!+-% feaafeart1ev1aaatCvAUfeBSjuyZL2yd9gzLbvyNv2CaerbuLwBLn% hiov2DGi1BTfMBaeXatLxBI9gBaerbd9wDYLwzYbItLDharqqtubsr% 4rNCHbGeaGqiVu0Je9sqqrpepC0xbbL8F4rqqrFfpeea0xe9Lq-Jc9% vqaqpepm0xbba9pwe9Q8fs0-yqaqpepae9pg0FirpepeKkFr0xfr-x% fr-xb9adbaqaaeGaciGaaiaabeqaamaabaabaaGcbaGaae4waKaaGi% aabseakiaab2cajaaOcaqGqbGcdaqgaaqaaKaaGkaabwgacaqGUbGc% daahaaWcbeqaaiaabkdaaaGccaGGSaqcaaIaaeiraiaab2cajaaOca% qGqbGaaeyzaaWcbaaakiaawYa7aKaaGkaab6gakmaaCaaaleqabaGa% aeynaaaakiaac2faaaa!475D!\[{\text{[D - P}}{\text{n}}^{\text{5}} ]\]

DPLPE:

% MathType!MTEF!2!1!+-% feaafeart1ev1aaatCvAUfeBSjuyZL2yd9gzLbvyNv2CaerbuLwBLn% hiov2DGi1BTfMBaeXatLxBI9gBaerbd9wDYLwzYbItLDharqqtubsr% 4rNCHbGeaGqiVu0Je9sqqrpepC0xbbL8F4rqqrFfpeea0xe9Lq-Jc9% vqaqpepm0xbba9pwe9Q8fs0-yqaqpepae9pg0FirpepeKkFr0xfr-x% fr-xb9adbaqaaeGaciGaaiaabeqaamaabaabaaGcbaGaae4waKaaGi% aabseakiaab2cajaaOcaqGqbGcdaqgaaqaaKaaGkaabwgacaqGUbGc% daahaaWcbeqaaiaabkdaaaGccaGGSaqcaaIaaeiraiaab2cajaaOca% qGqbGaaeyzaaWcbaaakiaawYa7aKaaGkaab6gakmaaCaaaleqabaGa% aeynaaaakiaac2faaaa!475D!\[{\text{[D - P}}{\text{n}}^{\text{5}} ]\]

Orn:

ornithine

Pen:

penicillamine

NMR:

nuclear magnetic resonance

VDW:

van der Waals

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Authors and Affiliations

  1. Laboratory of Chemical Biology and Peptide Research, Clinical Research Institute of Montreal, 110 Pine Avenue West, H2W 1R7, Montreal, Quebec, Canada

    Brian C. Wilkes & Peter W. Schiller

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  1. Brian C. Wilkes
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  2. Peter W. Schiller
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Additional information

Presented in part at the 11th American Peptide Symposium, La Jolla, CA, July 9–14, 1989.

Symbols and abbreviations are in accordance with the recommendations of the IUPAC-IUB Joint Commission on Biochemical Nomenclature: Biochem. J., 219 (1984) 345. The following other abbreviations were used

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Wilkes, B.C., Schiller, P.W. Comparative conformational analysis of % MathType!MTEF!2!1!+-% feaafeart1ev1aaatCvAUfeBSjuyZL2yd9gzLbvyNv2CaerbuLwBLn% hiov2DGi1BTfMBaeXatLxBI9gBaerbd9wDYLwzYbItLDharqqtubsr% 4rNCHbGeaGqiVu0Je9sqqrpepC0xbbL8F4rqqrFfpeea0xe9Lq-Jc9% vqaqpepm0xbba9pwe9Q8fs0-yqaqpepae9pg0FirpepeKkFr0xfr-x% fr-xb9adbaqaaeGaciGaaiaabeqaamaabaabaaGcbaGaae4waKaaGi% aabseakiaab2cajaaOcaqGqbGcdaqgaaqaaKaaGkaabwgacaqGUbGc% daahaaWcbeqaaiaabkdaaaGccaGGSaqcaaIaaeiraiaab2cajaaOca% qGqbGaaeyzaaWcbaaakiaawYa7aKaaGkaab6gakmaaCaaaleqabaGa% aeynaaaakiaac2faaaa!475D!\[{\text{[D - P}}{\text{n}}^{\text{5}} ]\] enkephalin (DPDPE): A molecular mechanics study. J Computer-Aided Mol Des 5, 293–302 (1991). https://doi.org/10.1007/BF00126664

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