Biotransformations of propenylbenzenes by an Arthrobacter sp. and its t-anethole blocked mutants

Propenylbenzenes are often used as starting materials in the chemical synthesis of aroma compounds and fine chemicals. In the present study, we demonstrate the ability of an Arthrobacter sp. to transform various structures of propenylbenzenes derived from essential oils to flavor, fragrance, and fin...

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Bibliographic Details
Published in:Journal of biotechnology 2003-10, Vol.105 (1), p.61-70
Main Authors: Shimoni, Eyal, Baasov, Timor, Ravid, Uzi, Shoham, Yuval
Format: Article
Language:English
Subjects:
Anisoles - metabolism
Arthrobacter
Arthrobacter - metabolism
Benzoates - metabolism
Biological and medical sciences
Biotechnology
Biotransformation
Coumaric Acids - metabolism
Essential oils
Fundamental and applied biological sciences. Psychology
hydroxychavicol
isoeugenol
Mutation
Oils, Volatile - chemistry
Oils, Volatile - metabolism
Propenylbenzene
propenylbenzenes
safrole
t-anethole
vanillic acid
Vanillic Acid - metabolism
vanillin
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Summary:Propenylbenzenes are often used as starting materials in the chemical synthesis of aroma compounds and fine chemicals. In the present study, we demonstrate the ability of an Arthrobacter sp. to transform various structures of propenylbenzenes derived from essential oils to flavor, fragrance, and fine chemicals. Arthrobacter strain TA13 and its t-anethole blocked mutants (incapable of growing on t-anethole) converted isoeugenol to vanillin and vanillic acid; and safrole to hydroxychavicol. High conversion efficiencies were achieved in the biotransformations of isosafrole to piperonylic acid, and eugenol to a mixture of ferulic acid and vanillic acid. In addition, anisic acid was produced in high yields from t-anethole, anisyl alcohol, or anisaldehyde. The accumulation of the corresponding aromatic acids from the tested propenylbenzenes is due to the lack of m-demethylase activity in strain TA13 that prevents further cleavage of the benzene ring. Interestingly, in the transformation of eugenol (a 2-propenylbenzene) the side chain was initially oxidized to the corresponding cinamic acid derivative (ferulic acid) while the 1-propenylbenzenes gave substituted benzoic acids, suggesting two different chain shortening mechanisms.
ISSN:0168-1656
1873-4863
DOI:10.1016/S0168-1656(03)00141-X