title: Full relative stereochemistry assignment and conformational analysis of 13,19-didesmethyl spirolide C via NMR- and molecular modeling-based techniques. A step towards understanding spirolide's mechanism of action.
abstract: The relative stereochemistry of 13,19-didesmethyl spirolide C was determined through careful analysis of NMR parameters strongly dependent upon molecular conformations supported and extended by computational studies. This work has also shed light on the conformational behavior of spirolides in solution. An equilibrium between two possible conformers of the identified diastereoisomer was inferred, while the uncommon cyclic imine moiety of spirolides-the putative pharmacophore of this class of toxins-was interestingly found to adopt only a single dominant conformation. The insightful details provided on spirolide conformations may represent a key means to pharmacologists involved in clarifying the mechanism of action of spirolide, which is yet to be totally defined.
authors.affiliation: Dipartimento di Chimica delle Sostanze Naturali, Università di Napoli Federico II, via D. Montesano, 49, 80131 Napoli, Italy.
authors.forename: Patrizia
authors.initials: P
authors.lastname: Ciminiello
authors.forename: Bruno
authors.initials: B
authors.lastname: Catalanotti
authors.forename: Carmela
authors.initials: C
authors.lastname: Dell'aversano
authors.forename: Caterina
authors.initials: C
authors.lastname: Fattorusso
authors.forename: Ernesto
authors.initials: E
authors.lastname: Fattorusso
authors.forename: Martino
authors.initials: M
authors.lastname: Forino
authors.forename: Laura
authors.initials: L
authors.lastname: Grauso
authors.forename: Angela
authors.initials: A
authors.lastname: Leo
authors.forename: Luciana
authors.initials: L
authors.lastname: Tartaglione
mesh_terms: D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008968:Molecular Conformation; D013141:Spiro Compounds / Q000737:chemistry*
chemical_list: C544516:13,19-didesmethyl spirolide C; D013141:Spiro Compounds