Efficient synthesis of hydroxystyrenes via biocatalytic decarboxylation/deacetylation of substituted cinnamic acids by newly isolated Pantoea agglomerans strains
IR@IHBT: CSIR-Institute of Himalayan Bioresource Technology, Palampur
View Archive Info| Field | Value | |
| Title |
Efficient synthesis of hydroxystyrenes via
biocatalytic decarboxylation/deacetylation
of substituted cinnamic acids by newly isolated
Pantoea agglomerans strains
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| Creator |
Sharma , U K
Sharma, N Salwan, R Kumar, R Kasana , Ramesh C Sinha, Arun K |
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| Subject |
Natural Product Chemistry
Plant viruses |
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| Description |
Abstract
BACKGROUND: Decarboxylation of substituted cinnamic acids is a predominantly followed pathway for obtaining
hydroxystyrenes – one of the most extensively explored bioactive compounds in the food and flavor industry (e.g. FEMA
GRAS approved 4-vinylguaiacol). For this, mild and green strategies providing good yields with high product selectivity are
needed.
RESULTS:Twonewly isolated bacterial strains, i.e. Pantoea agglomerans KJLPB4 and P. agglomerans KJPB2, are reported for mild
and effective decarboxylation of substituted cinnamic acids into corresponding hydroxystyrenes. Key operational parameters
for the process, such as incubation temperature, incubation time, substrate concentration and effect of co-solvent, were
optimized using ferulic acid as a model substrate. With strain KJLPB4, 1.51 g L−1 4-vinyl guaiacol (98% yield) was selectively
obtained from 2 g L−1 ferulic acid at 28 ◦C after 48 h incubation. However, KJPB2 provided vanillic acid in 85% yield after
72 h following the oxidative decarboxylation pathway. In addition, KJLPB4 was effectively exploited for the deacetylation of
acetylated α-phenylcinnamic acids, providing corresponding compounds in 65–95% yields.
CONCLUSION: Two newly isolated microbial strains are reported for the mild and selective decarboxylation of substituted
cinnamic acids into hydroxystyrenes. Preparative-scale synthesis of vinyl guaiacol and utilization of renewable feedstock
(ferulic acid extracted from maize bran) have been demonstrated to enhance the practical utility of the process.
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| Date |
2012
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| Type |
Article
PeerReviewed |
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| Format |
application/pdf
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| Identifier |
http://ihbt.csircentral.net/954/1/efficient_synthesis.pdf
Sharma , U K and Sharma, N and Salwan, R and Kumar, R and Kasana , Ramesh C and Sinha, Arun K (2012) Efficient synthesis of hydroxystyrenes via biocatalytic decarboxylation/deacetylation of substituted cinnamic acids by newly isolated Pantoea agglomerans strains. Journal of Sicence Food Agriculture, 92. pp. 610-617. |
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| Relation |
http://ihbt.csircentral.net/954/
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