Affiliation:
1. grid.413109.e 0000000097356249 Key Laboratory of Industrial Fermentation Microbiology, Ministry of Education, College of Biotechnology Tianjin University of Science and Technology 300457 Tianjin China
2. grid.9227.e 0000000119573309 National Engineering Laboratory for Industrial Enzymes, Tianjin Institute of Industrial Biotechnology Chinese Academy of Sciences 300308 Tianjin China
Abstract
Abstract
In the search for an effective biocatalyst for the reduction of acetophenones with unprotected hydroxy group on the benzene ring, a microorganism, which reduced para-acetylphenol to S-(−)-1-(para-hydroxyphenyl)ethanol under anaerobic conditions, was isolated from soil samples and the 16S rDNA study showed that it was phylogenetically affiliated with species of the genus Rhodococcus and was most similar to Rhodococcus pyridinivorans. Unexpectedly, this strain also hydroxylated para-acetylphenol to give 4-acetylcatechol in presence of oxygen, possessing para-acetylphenol hydroxylase activity. While the reduction of para-acetylphenol had an optimal reaction pH at 7 and a broad optimal temperature range (35–45 °C), the hydroxylation reached the maximum conversion at the pH range of 7–8 and 35 °C. This study identified for the first time a Rhodococcus strain with para-acetylphenol hydroxylase activity, which also contains highly enantioselective carbonyl reductase activity with potential applications for the asymmetric reduction of these less-explored but important ketones such as α-aminoacetophenone, 3′-hydroxyacetophenone and 4′-hydroxyacetophenone. The para-acetylphenol hydroxylase and carbonyl reductase activity are switchable by the reaction conditions.
Publisher
Oxford University Press (OUP)
Subject
Applied Microbiology and Biotechnology,Biotechnology,Bioengineering
Reference49 articles.
1. β3 and atypical β-adrenoceptors;Arch;Med Res Rev,1993
2. Synthesis of the β2 agonist (R)-salmeterol using a sequence of supported reagents and scavenging agents;Bream;Org Lett,2002
3. Looker BE (2005) A short stereoselective synthesis of (R)-salmeterol;Buchanan;Synlett,2005
4. Potassium trimethylsilanolate induced cleavage of 1,3-oxazolidin-2- and 5-ones, and application to the synthesis of (R)-salmeterol;Coe;Org Biomol Chem,2003
5. Hydroquinone as the ring-fission substrate in the catabolism of 4-ethylphenol and 4-hydroxyacetophenone by Pseudomonas putida JD1;Darby;J Gen Microbiol,1987
Cited by
6 articles.
订阅此论文施引文献
订阅此论文施引文献,注册后可以免费订阅5篇论文的施引文献,订阅后可以查看论文全部施引文献