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- W2619467199 abstract "Green and selective oxidation methods are highly desired in chemical synthesis and manufacturing. In this work, we have developed a biocatalytic method for the regio- and stereoselective oxidation of styrene derivatives into arylacetic and (S)-2-arylpropionic acids via a one-pot epoxidation–isomerization–oxidation sequence. This was done via the engineering of Escherichia coli (StyABC-EcALDH) coexpressing styrene monooxygenase (SMO), styrene oxide isomerase (SOI) and aldehyde dehydrogenase (EcALDH) as an active and easily available whole-cell catalyst. Regioselective oxidation of styrene and 11 substituted styrenes using the E. coli cells was performed in a one-pot set-up, producing 12 phenylacetic acids in both high conversion and high yield. Engineering of E. coli (StyABC-ADH9v1) coexpressing SMO, SOI and ADH9v1 (a mutated alcohol dehydrogenase) led to biocatalysts capable of regio- and stereoselective oxidation of α-methylstyrene derivatives to the corresponding chiral acids. One-pot asymmetric synthesis of 4 (S)-2-arylpropionic acids was achieved in good conversion and excellent ee with the E. coli cells. This is a new type of asymmetric alkene oxidation to give chiral acids with no chemical counterpart thus far. The cascade bio-oxidation operates under mild conditions, uses molecular oxygen, exhibits very high regio- and enantioselectivity, and gives high conversion, thus providing a green and efficient method for the synthesis of arylacetic acids and (S)-2-arylpropionic acids directly from easily available styrenes." @default.
- W2619467199 created "2017-06-05" @default.
- W2619467199 creator A5004328816 @default.
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- W2619467199 creator A5032437066 @default.
- W2619467199 creator A5086948303 @default.
- W2619467199 date "2017-06-07" @default.
- W2619467199 modified "2023-10-12" @default.
- W2619467199 title "Regio- and Stereoselective Oxidation of Styrene Derivatives to Arylalkanoic Acids<i>via</i>One-Pot Cascade Biotransformations" @default.
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- W2619467199 doi "https://doi.org/10.1002/adsc.201700416" @default.
- W2619467199 hasPublicationYear "2017" @default.
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