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Volume 271, Number 46, Issue of November 15, 1996 pp. 28861-28867
©1996 by The American Society for Biochemistry and Molecular Biology, Inc.

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Xanthophyll Biosynthesis
CLONING, EXPRESSION, FUNCTIONAL RECONSTITUTION, AND REGULATION OF -CYCLOHEXENYL CAROTENOID EPOXIDASE FROM PEPPER (CAPSICUM ANNUUM)

(Received for publication, July 8, 1996, and in revised form, August 28, 1996)

Florence Bouvier , Alain d'Harlingue ^§ , Philippe Hugueney ^¶ , Elena Marin , Annie Marion-Poll and Bilal Camara

From the  Institut de Biologie Moléculaire des Plantes du Centre National de la Recherche Scientifique, Université Louis Pasteur, 12 rue du Général Zimmer, 67084 Strasbourg, France, the ^§ Laboratoire de Pathologie et Biochimie Végétales, Université Pierre et Marie Curie, 4 Place Jussieu, 75250 Paris, France, the ^¶ Institut für Biologie II Zellbiologie Schänzlestrasse 1d 79104, Germany, and the  Laboratoire de Biologie Cellulaire, Institut National de la Recherche Agronomique, 78026 Versailles Cedex, France

Pepper (Capsicum annuum) -cyclohexenyl xanthophyll epoxidase cDNA was cloned and the corresponding enzyme overexpressed and purified from Escherichia coli, for investigation of its catalytic activity. The recombinant protein did not directly accept NADPH for epoxidation of cyclohexenyl carotenoids, nor did it operate according to a peroxygenase-based mechanism. Instead, the reducing power of NADPH was transferred to the epoxidase via reduced ferredoxin as shown by reconstitution of epoxidase activity in the presence of NADPH, ferredoxin oxidoreductase, and ferredoxin. Bacterial rubredoxin could be substituted for ferredoxin. The pepper epoxidase acted specifically on the -ring of xanthophylls such as -cryptoxanthin, zeaxanthin, and antheraxanthin. The proposed reaction mechanism for epoxidation involves the formation of a transient carbocation. This characteristic allows selective inhibition of the epoxidase activity by different nucleophilic diethylamine derivatives, p-dimethylaminobenzenediazonium fluoroborate and N,N-dimethyl-2-phenylaziridinium. It was also shown that the epoxidase gene was up-regulated during oxidative stress and when chloroplasts undergo differentiation into chromoplasts in pepper fruit.

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