Document Detail

Isolation of a gene responsible for the oxidation of trans-anethole to para-anisaldehyde by Pseudomonas putida JYR-1 and its expression in Escherichia coli.
MedLine Citation:
PMID:  22610435     Owner:  NLM     Status:  MEDLINE    
A plasmid, pTA163, in Escherichia coli contained an approximately 34-kb gene fragment from Pseudomonas putida JYR-1 that included the genes responsible for the metabolism of trans-anethole to protocatechuic acid. Three Tn5-disrupted open reading frame 10 (ORF 10) mutants of plasmid pTA163 lost their abilities to catalyze trans-anethole. Heterologously expressed ORF 10 (1,047 nucleotides [nt]) under a T7 promoter in E. coli catalyzed oxidative cleavage of a propenyl group of trans-anethole to an aldehyde group, resulting in the production of para-anisaldehyde, and this gene was designated tao (trans-anethole oxygenase). The deduced amino acid sequence of TAO had the highest identity (34%) to a hypothetical protein of Agrobacterium vitis S4 and likely contained a flavin-binding site. Preferred incorporation of an oxygen molecule from water into p-anisaldehyde using (18)O-labeling experiments indicated stereo preference of TAO for hydrolysis of the epoxide group. Interestingly, unlike the narrow substrate range of isoeugenol monooxygenase from Pseudomonas putida IE27 and Pseudomonas nitroreducens Jin1, TAO from P. putida JYR-1 catalyzed isoeugenol, O-methyl isoeugenol, and isosafrole, all of which contain the 2-propenyl functional group on the aromatic ring structure. Addition of NAD(P)H to the ultrafiltered cell extracts of E. coli (pTA163) increased the activity of TAO. Due to the relaxed substrate range of TAO, it may be utilized for the production of various fragrance compounds from plant phenylpropanoids in the future.
Dongfei Han; Ji-Young Ryu; Robert A Kanaly; Hor-Gil Hur
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't     Date:  2012-05-18
Journal Detail:
Title:  Applied and environmental microbiology     Volume:  78     ISSN:  1098-5336     ISO Abbreviation:  Appl. Environ. Microbiol.     Publication Date:  2012 Aug 
Date Detail:
Created Date:  2012-07-19     Completed Date:  2012-12-10     Revised Date:  2013-06-24    
Medline Journal Info:
Nlm Unique ID:  7605801     Medline TA:  Appl Environ Microbiol     Country:  United States    
Other Details:
Languages:  eng     Pagination:  5238-46     Citation Subset:  IM    
School of Environmental Science and Engineering, Gwangju Institute of Science and Technology, Gwangju, Republic of Korea.
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MeSH Terms
Anisoles / metabolism*
Base Sequence
Benzaldehydes / metabolism*
Chromatography, High Pressure Liquid
DNA Primers / genetics
Escherichia coli
Gene Library
Genes, Bacterial / genetics*
Mass Spectrometry
Metabolic Networks and Pathways / genetics*
Molecular Sequence Data
Oxygen Isotopes / metabolism
Oxygenases / genetics*
Plasmids / genetics
Pseudomonas putida / enzymology,  genetics*
Sequence Analysis, DNA
Reg. No./Substance:
0/Anisoles; 0/Benzaldehydes; 0/DNA Primers; 0/Oxygen Isotopes; 9PA5V6656V/4-anisaldehyde; EC 1.13.-/Oxygenases; Q3JEK5DO4K/anethole

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