Non-natural cinnamic acid derivatives as substrates of cinnamate 4-hydroxylase |
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Authors: | Chen Hao Jiang Hanxiao Morgan John A |
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Affiliation: | School of Chemical Engineering, Purdue University, 1055 FRNY Hall, West Lafayette, IN 47907-1283, USA. |
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Abstract: | Cinnamate 4-hydroxylase (C4H), a monooxygenase in the plant phenylpropanoid pathway, was assayed for its ability to hydroxylate 29 substrate analogues. Nine of the tested analogues with various aromatic side chains, including 3-coumaric acid, were metabolized by C4H. Seven products from these reactive analogues were characterized using LC/MS, 1H NMR and 13C NMR spectroscopic analysis. For example, caffeic acid was the product of 3-coumaric acid. The products 4-hydroxy-2-chlorocinnamic acid and 4-hydroxy-2-ethoxycinnamic acid are novel compounds that have not been previously reported. The kinetic parameters of C4H towards these analogues were determined. |
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Keywords: | Arabidopsis thaliana Cruciferae Saccharomyces cerevisiae Cytochrome P450 Phenylpropanoids Coumaric acid |
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