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.