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Microbial Synthesis of Medium‐Chain α,ω‐Dicarboxylic Acids and ω‐Aminocarboxylic Acids from Renewable Long‐Chain Fatty Acids
Author(s) -
Song JiWon,
Lee JungHoo,
Bornscheuer Uwe T.,
Park JinByung
Publication year - 2014
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201300784
Subject(s) - ricinoleic acid , chemistry , pseudomonas putida , amino acid , biocatalysis , oleic acid , organic chemistry , fatty acid , alcohol dehydrogenase , biochemistry , enzyme , catalysis , ionic liquid , castor oil
Biotransformation of long‐chain fatty acids into medium‐chain α,ω‐dicarboxylic acids or ω‐aminocarboxylic acids could be achieved with biocatalysts. This study presents the production of α,ω‐dicarboxylic acids (e.g., C 9 , C 11 , C 12 , C 13 ) and ω‐aminocarboxylic acids (e.g., C 11 , C 12 , C 13 ) directly from fatty acids (e.g., oleic acid, ricinoleic acid, lesquerolic acid) using recombinant Escherichia coli ‐based biocatalysts. ω‐Hydroxycarboxylic acids, which were produced from oxidative cleavage of fatty acids via enzymatic reactions involving a fatty acid double bond hydratase, an alcohol dehydrogenase, a Baeyer–Villiger monooxygenase and an esterase, were then oxidized to α,ω‐dicarboxylic acids by alcohol dehydrogenase (ADH, AlkJ) from Pseudomonas putida GPo1 or converted into ω‐aminocarboxylic acids by a serial combination of ADH from P. putida GPo1 and an ω‐transaminase of Silicibacter pomeroyi . The double bonds present in the fatty acids such as ricinoleic acid and lesquerolic acid were reduced by E. coli ‐native enzymes during the biotransformations. This study demonstrates that the industrially relevant building blocks (C 9 to C 13 saturated α,ω‐dicarboxylic acids and ω‐aminocarboxylic acids) can be produced from renewable fatty acids using biocatalysis.