Please use this identifier to cite or link to this item:
https://hdl.handle.net/2440/100955
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Type: | Journal article |
Title: | The efficient and selective catalytic oxidation of para-substituted cinnamic acid derivatives by the cytochrome P450 monooxygenase, CYP199A4 |
Author: | Chao, R. De Voss, J. Bell, S. |
Citation: | RSC Advances: an international journal to further the chemical sciences, 2016; 6(60):55286-55297 |
Publisher: | Royal Society of Chemistry |
Issue Date: | 2016 |
ISSN: | 2046-2069 2046-2069 |
Statement of Responsibility: | Rebecca R. Chao, James J. De Voss and Stephen G. Bell |
Abstract: | The cytochrome P450 enzyme, CYP199A4, demethylated 4-methoxybenzoic acid, but not 4-methoxyphenylacetic acid, with high product formation activity. The oxidative demethylation of 3-(4-methoxyphenyl)propionic acid was 8-fold more active than 4-methoxyphenylacetic acid and 4-methoxycinnamic acid was efficiently oxidised at a product formation rate of 180 nmol nmol-P450−1 min−1. Accordingly the oxidation of cinnamic acid derivatives was investigated in order to determine the potential of CYP199A4 to act as a biocatalyst for this important class of biological molecules. 4-Methoxy- and 4-methyl-cinnamic acids bound tightly to CYP199A4 and were better substrates for CYP199A4 than cinnamic acid itself. The oxidations of both 4-methoxy- and 4-methyl-cinnamic acids was 100% selective for attack at the para substituent. Certain dimethoxy substituted cinnamic acids were demethylated more efficiently than 4-methoxycinnamic acid and retained the selectivity for the para-methoxy substituent. Only very low product turnover was observed with 3,5-dimethoxycinnamic acid. 4-Isopropylcinnamic acid was hydroxylated and desaturated by CYP199A4 at the isopropyl group. Cinnamic acids with a para-substituted alkyl- and alkyloxy–cinnamic acid framework were a good fit for the active site of the CYP199A4 enzyme and as a consequence were efficiently and selectively oxidised. Whole-cell oxidations resulted in high yields of product and CYP199A4 could be developed for applications in the biocatalytic oxidation of cinnamic acid derivatives and related phenylpropanoids. |
Description: | First published online 03 Jun 2016 |
Rights: | This journal is © The Royal Society of Chemistry 2016 |
DOI: | 10.1039/c6ra11025h |
Grant ID: | http://purl.org/au-research/grants/arc/DP140103229 http://purl.org/au-research/grants/arc/FT140100355 |
Published version: | http://dx.doi.org/10.1039/c6ra11025h |
Appears in Collections: | Aurora harvest 3 Chemistry publications |
Files in This Item:
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hdl_100955.pdf | Accepted version | 1.45 MB | Adobe PDF | View/Open |
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