Unpredictable Stereochemical Preferences for Mu Opioid Receptor Activity in an Exhaustively Stereodiversified Library of 1,4-Enediols
- 11 February 2003
- journal article
- research article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 5 (5) , 633-636
- https://doi.org/10.1021/ol027237f
Abstract
Using olefin cross-metathesis, we synthesized a novel stereodiversified library of compounds 3 containing a trans-1,4-enediol. Screening this library for mu opioid receptor (MOR) affinity identified multiple high-affinity ligands and revealed that the stereochemical configuration varied widely among those ligands having the highest affinity. It was not possible to predict the configurations of the most active compounds 3 on the basis of the configuration of endomorphin-2, a known MOR peptide ligand, validating the diversity-based approach to ligand discovery.Keywords
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