title: Conformational studies on resiniferatoxin (RTX), an ultrapotent vanilloid agonist.
abstract: In polar solution, NOE studies show a pronounced clustering of the aromatic moieties (9,13,14-phenylacetate orthoester and 20-homovanillate) of the ultrapotent vanilloid agonist resiniferatoxin (RTX). This clustering is absent in nonpolar solution. Low energy clustered structures from molecular dynamics simulations account for the observed NOEs. These results suggest that the phenylorthoacetate moiety can assist the attainment of specific alignments between the terpenoid core and the vanillyl moiety, possibly preorganizing them for ideal receptor binding.
authors.affiliation: Department of Medicinal Chemistry, University of Kansas, Lawrence 66045, USA. svictory@ukans.edu; dvandervelde@ukans.edu
authors.forename: S F
authors.initials: SF
authors.lastname: Victory
authors.forename: G
authors.initials: G
authors.lastname: Appendino
authors.forename: D G
authors.initials: DG
authors.lastname: Vander Velde
mesh_terms: D004224:Diterpenes / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008968:Molecular Conformation; D009498:Neurotoxins / Q000737:chemistry*
chemical_list: D004224:Diterpenes; D009498:Neurotoxins; C024353:resiniferatoxin