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Biotransformations of propenylbenzenes by an Arthrobacter sp. and its t-anethole blocked mutants
Year:
2003
Source of publication :
Journal of Biotechnology
Authors :
Ravid, Uzi
;
.
Volume :
105
Co-Authors:
Shimoni, E., Dept. of Food Eng. and Biotechnology, Technion-Israel Inst. of Technology, Haifa 32000, Israel, Inst. of Catalys. Sci./Technology, Technion-Israel Inst. of Technology, Haifa 32000, Israel
Baasov, T., Inst. of Catalys. Sci./Technology, Technion-Israel Inst. of Technology, Haifa 32000, Israel, Department of Chemistry, Technion-Israel Inst. of Technology, Haifa 32000, Israel
Ravid, U., A.R.O., Newe Ya'ar Research Center, P.O.B. 1021, Ramat Yishai 30095, Israel
Shoham, Y., Dept. of Food Eng. and Biotechnology, Technion-Israel Inst. of Technology, Haifa 32000, Israel, Inst. of Catalys. Sci./Technology, Technion-Israel Inst. of Technology, Haifa 32000, Israel
Facilitators :
From page:
61
To page:
70
(
Total pages:
10
)
Abstract:
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. © 2003 Elsevier B.V. All rights reserved.
Note:
Related Files :
anethole
biotechnology
biotransformation
essential oils
mutation
piperonylic acid
unclassified drug
Show More
Related Content
More details
DOI :
10.1016/S0168-1656(03)00141-X
Article number:
Affiliations:
Database:
Scopus
Publication Type:
article
;
.
Language:
English
Editors' remarks:
ID:
29376
Last updated date:
02/03/2022 17:27
Creation date:
17/04/2018 00:46
Scientific Publication
Biotransformations of propenylbenzenes by an Arthrobacter sp. and its t-anethole blocked mutants
105
Shimoni, E., Dept. of Food Eng. and Biotechnology, Technion-Israel Inst. of Technology, Haifa 32000, Israel, Inst. of Catalys. Sci./Technology, Technion-Israel Inst. of Technology, Haifa 32000, Israel
Baasov, T., Inst. of Catalys. Sci./Technology, Technion-Israel Inst. of Technology, Haifa 32000, Israel, Department of Chemistry, Technion-Israel Inst. of Technology, Haifa 32000, Israel
Ravid, U., A.R.O., Newe Ya'ar Research Center, P.O.B. 1021, Ramat Yishai 30095, Israel
Shoham, Y., Dept. of Food Eng. and Biotechnology, Technion-Israel Inst. of Technology, Haifa 32000, Israel, Inst. of Catalys. Sci./Technology, Technion-Israel Inst. of Technology, Haifa 32000, Israel
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 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. © 2003 Elsevier B.V. All rights reserved.
Scientific Publication
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