Syntheses of ylidenbutenolide-modified derivatives of peridinin and their stereochemical and spectral characteristics.
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.
Kajikawa
Takayuki
T
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.
Aoki
Kazuyoshi
K
Iwashita
Takashi
T
Niedzwiedzki
Dariusz M
DM
Frank
Harry A
HA
Katsumura
Shigeo
S
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
C016040:peridinin; D002338:Carotenoids; C004511:butenolide; D015107:4-Butyrolactone