초록
<P><B>Abstract</B></P><P>A practical chemoenzymatic method for the synthesis of 9‐hydroxynonanoic acid and 1,9‐nonanedioic acid (i.e., azelaic acid) from oleic acid [(9<I>Z</I>)‐octadec‐9‐enoic acid] was investigated. Biotransformation of oleic acid into 9‐(nonanoyloxy)nonanoic acid <I>via</I> 10‐hydroxyoctadecanoic acid and 10‐keto‐octadecanoic acid was driven by a C‐9 double bond hydratase from <I>Stenotrophomonas maltophilia</I>, an alcohol dehydrogenase from <I>Micrococcus luteus</I>, and a Baeyer–Villiger monooxygenase (BVMO) from <I>Pseudomonas putida</I> KT2440, which was expressed in recombinant <I>Escherichia coli</I>. After production of the ester (i.e., the BVMO reaction product), the compound was chemically hydrolyzed to <I>n</I>‐nonanoic acid and 9‐hydroxynonanoic acid because <I>n</I>‐nonanoic acid is toxic to <I>E. coli</I>. The ester was also converted into 9‐hydroxynonanoic acid and the <I>n</I>‐nonanoic acid methyl ester, which can be oxygenated into the 9‐hydroxynonanoic acid methyl ester by the AlkBGT from <I>P. putida</I> GPo1. Finally, 9‐hydroxynonanoic acid was chemically oxidized to azelaic acid with a high yield under fairly mild reaction conditions. For example, whole‐cell biotransformation at a high cell density (i.e., 10 g dry cells/L) allowed the final ester product concentration and volumetric productivity to reach 25 mM and 2.8 mM h<SUP>−1</SUP>, respectively. The overall molar yield of azelaic acid from oleic acid was 58%, based on the biotransformation and chemical transformation conversion yields of 84% and 68%, respectively.</P>