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Concurrent obtaining of aromatic (R)-2-hydroxyacids and aromatic 2-ketoacids by asymmetric oxidation with a newly isolated Pseudomonas aeruginosa ZJB1125

Paper ID Volume ID Publish Year Pages File Format Full-Text
23506 43444 2013 8 PDF Available
Title
Concurrent obtaining of aromatic (R)-2-hydroxyacids and aromatic 2-ketoacids by asymmetric oxidation with a newly isolated Pseudomonas aeruginosa ZJB1125
Abstract

•Concurrent obtaining of aromatic (R)-2-HA and aromatic 2-KA was demonstrated.•P. aeruginosa ZJB1125 displayed pretty high enantioselectivity for aromatic 2-HA.•An efficient method was established to separate aromatic (R)-2-HA and aromatic 2-KA.•A novel methodology was provided to utilize racemic aromatic 2-HA efficiently.

Pseudomonas aeruginosa ZJB1125 harboring a stereoselective 2-hydroxyacid dehydrogenase (2-HADH) can catalyze asymmetric oxidation of mandelic acid and 2-chloromandelic acid into (R)-isomers and corresponding 2-ketoacids with high activity and enantioselectivity, while no consecutive oxidation of 2-ketoacids was observed during whole-cell catalysis. The 2-HADH in P. aeruginosa ZJB1125 is a FMN-dependent flavoprotein and did not require NAD(P)+ as cofactors to catalyze the oxidation reaction. Enzyme activity staining identified 2-HADH as the key enzyme that enantioselectively oxidized (S)-hydroxyacid to 2-ketoacid. The 2-HADH in P. aeruginosa ZJB1125 is inducible and 2-chloromandelic acid was found to induce its synthesis efficiently. The bacterium displayed pretty high activity and enantioselectivity for most of the aromatic 2-hydroxyacids examined, and have a potential for the concurrent obtaining of aromatic (R)-2-hydroxyacids and aromatic 2-ketoacids in near theoretical conversions. Using a simple organic extract process, aromatic (R)-2-hydroxyacids and aromatic 2-ketoacids can be effectively separated from the biocatalytic reaction mixture with high yield (>95%). This work provided a novel method for the concurrent obtaining of aromatic (R)-2-hydroxyacids and aromatic 2-ketoacids by oxidation of aromatic 2-hydroxyacids in one-step biotransformation, which would be a valuable process due to its high atom economy.

Keywords
Asymmetric oxidation; Pseudomonas aeruginosa; (R)-2-Hydroxyacid; 2-Ketoacid
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Concurrent obtaining of aromatic (R)-2-hydroxyacids and aromatic 2-ketoacids by asymmetric oxidation with a newly isolated Pseudomonas aeruginosa ZJB1125
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Publisher
Database: Elsevier - ScienceDirect
Journal: Journal of Biotechnology - Volume 167, Issue 3, 10 September 2013, Pages 271–278
Authors
, , , , , ,
Subjects
Physical Sciences and Engineering Chemical Engineering Bioengineering
Get Full-Text Now
Don't Miss Today's Special Offer
Price was $35.95
You save - $31
Price after discount Only $4.95
100% Money Back Guarantee
Full-text PDF Download
Online Support
Any Questions? feel free to contact us