Premium
Efficient synthesis of hydroxystyrenes via biocatalytic decarboxylation/deacetylation of substituted cinnamic acids by newly isolated Pantoea agglomerans strains
Author(s) -
Sharma Upendra K,
Sharma Nandini,
Salwan Richa,
Kumar Rakesh,
Kasana Ramesh C,
Sinha Arun K
Publication year - 2012
Publication title -
journal of the science of food and agriculture
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.782
H-Index - 142
eISSN - 1097-0010
pISSN - 0022-5142
DOI - 10.1002/jsfa.4616
Subject(s) - decarboxylation , chemistry , guaiacol , cinnamic acid , ferulic acid , pantoea agglomerans , organic chemistry , oxidative decarboxylation , substrate (aquarium) , yield (engineering) , food science , bran , biochemistry , enzyme , bacteria , catalysis , raw material , biology , genetics , ecology , materials science , metallurgy
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: Two newly 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. Copyright © 2011 Society of Chemical Industry