title: Syntheses of ylidenbutenolide-modified derivatives of peridinin and their stereochemical and spectral characteristics.
abstract: Peridinin is a light-harvesting carotenoid found in oceanic photosynthetic organisms. It possesses a unique gamma-ylidenbutenolide function and engages in energy transfer to chlorophyll a with very high (>90%) efficiency. In order to examine the relationship between the unique structure of peridinin and its facility in carrying out energy transfer, we have synthesized two different ylidenbutenolide-modified derivatives of peridinin. In this communication, the details of the syntheses are described as are the stereochemical and spectral characteristics of the derivatives; the novel ylidenbutenolide functional group stabilizes the molecule and maintains the conjugated pi-electron system in an all-trans configuration.
authors.affiliation: Department of Chemistry and Open Research Center on Organic Tool Molecules, School of Science and Technology, Kwansei Gakuin University, Gakuen 2-1, Sanda, Hyogo 669-1337, Japan.
authors.forename: Takayuki
authors.initials: T
authors.lastname: Kajikawa
authors.forename: Kazuyoshi
authors.initials: K
authors.lastname: Aoki
authors.forename: Takashi
authors.initials: T
authors.lastname: Iwashita
authors.forename: Dariusz M
authors.initials: DM
authors.lastname: Niedzwiedzki
authors.forename: Harry A
authors.initials: HA
authors.lastname: Frank
authors.forename: Shigeo
authors.initials: S
authors.lastname: Katsumura
mesh_terms: D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D002338:Carotenoids / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013057:Spectrum Analysis; D013237:Stereoisomerism
chemical_list: C016040:peridinin; D002338:Carotenoids; C004511:butenolide; D015107:4-Butyrolactone