Issue 11, 2010
From the journal:

Organic & Biomolecular Chemistry

Syntheses of ylidenbutenolide-modified derivatives of peridinin and their stereochemical and spectral characteristics†

Takayuki Kajikawa,a   Kazuyoshi Aoki,a   Takashi Iwashita,b   Dariusz M. Niedzwiedzki,c   Harry A. Frankc  and  Shigeo Katsumura*a  

* Corresponding authors

a 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
E-mail: katsumura@kwansei.ac.jp
Fax: +81-79-565-9077
Tel: +81-79-565-8314

b Suntory Institute For Bioorganic Research, Wakayamadai 1-1-1, Shimamoto, Mishimagunn, Osaka 618-8503, Japan
E-mail: iwashita@sunbor.or.jp
Fax: +81-79-962-2115
Tel: +81-75-962-1660

c Department of Chemistry, University of Connecticut, 55 North Eagleville Road, Storrs, CT 06269-3060, USA
E-mail: harry.frank@uconn.edu
Fax: +1-860-486-6558
Tel: +1-860-486-2844

Abstract

Peridinin is a light-harvesting carotenoid found in oceanic photosynthetic organisms. It possesses a unique γ-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 π-electron system in an all-trans configuration.

Graphical abstract: Syntheses of ylidenbutenolide-modified derivatives of peridinin and their stereochemical and spectral characteristics

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Article information

DOI
https://doi.org/10.1039/C002006K
Article type
Communication
Submitted
01 Feb 2010
Accepted
14 Apr 2010
First published
23 Apr 2010

Org. Biomol. Chem., 2010,8, 2513-2516

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Syntheses of ylidenbutenolide-modified derivatives of peridinin and their stereochemical and spectral characteristics

T. Kajikawa, K. Aoki, T. Iwashita, D. M. Niedzwiedzki, H. A. Frank and S. Katsumura, Org. Biomol. Chem., 2010, 8, 2513 DOI: 10.1039/C002006K

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