Non-natural cinnamic acid derivatives as substrates of cinnamate 4-hydroxylase.
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.
Chen
Hao
H
School of Chemical Engineering, Purdue University, 1055 FRNY Hall, West Lafayette, IN 47907-1283, USA.
Jiang
Hanxiao
H
Morgan
John A
JA
D002851:Chromatography, High Pressure Liquid; D002934:Cinnamates / Q000737:chemistry*; D003470:Culture Media; D007700:Kinetics; D013057:Spectrum Analysis / Q000379:methods*; D013379:Substrate Specificity; D050564:Trans-Cinnamate 4-Monooxygenase / Q000378:metabolism*
D002934:Cinnamates; D003470:Culture Media; C029010:cinnamic acid; D050564:Trans-Cinnamate 4-Monooxygenase