Probing the stereochemical requirements for receptor recognition of δ opioid agonists through topographic modifications in position 1

…, MD Shenderovich, KE Kövér, P Davis…

Index: Qian; Shenderovich; Kover; Davis; Horvath; Zalewska; Yamamura; Porreca; Hruby Journal of the American Chemical Society, 1996 , vol. 118, # 31 p. 7280 - 7290

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Citation Number: 70

Abstract

A series of side-chain constrained tyrosine derivatives, 2', 6'-dimethyl-β-methyltyrosines (TMT), has been designed and incorporated into position 1 of the highly selective δ opioid agonists DPDPE (Tyr-d-Pen2-Gly-Phe-d-Pen5-OH) and deltorphin I (DELT I, Tyr-d-Ala-Phe- Asp-Val-Val-Gly-NH2). Molecular mechanics calculations on isolated TMT residues and nuclear magnetic resonance (NMR) studies of the TMT1-containing peptides in DMSO ...