title: Computational study of conformational and chiroptical properties of (2R,3S,4R)-(+)-3,3',4,4',7-flavanpentol.
abstract: Conformational analysis of (2R,3S,4R)-(+)-3,3',4,4',7-flavanpentol, a flavonoid compound displaying both antioxidant and pro-oxidant properties, is performed by molecular mechanics and density functional theory calculations both in the gas phase and in methanol solution by using the Polarizable Continuum Model. Nine different conformations are identified. Absorption (UV) and circular dichroism (CD) spectra and optical rotations are calculated by means of time dependent density functional theory (TDDFT) and compared with experiments. The effects of a complex environment formed by water and proline-rich peptide molecules on the conformational characteristics of (2R,3S,4R)-(+)-3,3',4,4',7-flavanpentol and therefore on its UV and CD spectra are investigated by atomistic molecular dynamics simulations.
authors.affiliation: PolyLab-CNR-INFM, c/o Dipartimento di Chimica e Chimica Industriale, Università di Pisa, Italy.
authors.forename: Chiara
authors.initials: C
authors.lastname: Cappelli
authors.forename: Simona
authors.initials: S
authors.lastname: Bronco
authors.forename: Susanna
authors.initials: S
authors.lastname: Monti
mesh_terms: D002392:Catechin / Q000031:analogs & derivatives* / Q000737:chemistry; D002942:Circular Dichroism; D003198:Computer Simulation; D047309:Flavones; D005419:Flavonoids / Q000737:chemistry*; D006860:Hydrogen Bonding; D000432:Methanol; D008956:Models, Chemical; D008968:Molecular Conformation; D010455:Peptides / Q000737:chemistry; D012996:Solutions; D013056:Spectrophotometry, Ultraviolet; D013237:Stereoisomerism
chemical_list: C507397:3,3',4,4',7-flavanpentol; D047309:Flavones; D005419:Flavonoids; D010455:Peptides; D012996:Solutions; D002392:Catechin; C043562:flavone; D000432:Methanol