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Journal Article

Biosynthesis of psoralen: Mechanism of a cytochrome p450 catalyzed oxidative bond cleavage

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Boland,  W.
Department of Bioorganic Chemistry, MPI for Chemical Ecology, Max Planck Society;

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Citation

Stanjek, V., Miksch, M., Lueer, P., Matern, U., & Boland, W. (1999). Biosynthesis of psoralen: Mechanism of a cytochrome p450 catalyzed oxidative bond cleavage. Angewandte Chemie, International Edition in English, 38(3), 400-402. doi:10.1002/(SICI)1521-3773(19990201)38:3<400:AID-ANIE400>3.0.CO;2-K.


Cite as: http://hdl.handle.net/11858/00-001M-0000-0012-A3AA-D
Abstract
In contrast to the stepwise oxidative dealkylation of steroids [Eq. (1)], (+)‐marmesin (1) is directly converted by the psoralen synthase (a cytochrome P450) into the phototoxic furanocoumarin psoralen (2) and acetone. The dealkylation proceeds as a syn elimination.