Enhanced induction of cytochromes P450alk that oxidize methyl-ends of n-alkanes and fatty acids in the long-chain dicarboxylic acid-hyperproducing mutant of Candida maltosa

Kogure, Takahisa; Horiuchi, Hiroyuki; Matsuda, Hitoshi; Arie, Mami; Takagi, Masamichi; Ohta, Akio

doi:10.1111/j.1574-6968.2007.00705.x

Cited by 14 publications

(6 citation statements)

References 24 publications

(36 reference statements)

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“…However, the C. maltosa CYP52A10 and CYP52A11 enzymes are only able to convert fatty acids [23,24]. It is not completely clear which gene(s) exactly mediate dicarboxylic acid formation, but Kogure et al [25] demonstrated that the alk5 gene (CYP52A9) was highly induced when comparing a C. maltosa dicarboxylic acid overproducing mutant with a reference strain. Interestingly, P450alk5 is indeed the isozyme with the strongest tendency to x-hydroxylate fatty acids.…”

Section: Fatty Acid Degradation -Omega Oxidationmentioning

confidence: 99%

The role of cytochrome P450 monooxygenases in microbial fatty acid metabolism

et al. 2010

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Cytochrome P450 monooxygenases (P450s) are a diverse collection of enzymes acting on various endogenous and xenobiotic molecules. Most of them catalyse hydroxylation reactions and one group of possible substrates are fatty acids and their related structures. In this minireview, the significance of P450s in microbial fatty acid conversion is described. Bacteria and yeasts possess various P450 systems involved in alkane and fatty acid degradation, and often several enzymes with different activities and specificities are retrieved in one organism. Furthermore, P450s take part in the formation of fatty acid-based secondary metabolites. Finally, there are a substantial number of microbial P450s displaying activity towards fatty acids, but to which no biological role could be assigned despite the often quite intense research.

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Section: Fatty Acid Degradation -Omega Oxidationmentioning

confidence: 99%

The role of cytochrome P450 monooxygenases in microbial fatty acid metabolism

et al. 2010

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“…For a DCA-overproducing Candida maltosa strain, individual addition of n -decane and n -tetradecane induced the expression of the major cytochrome P450 monooxygenases (ALKs) catalyzing the first step of the alkane-assimilation pathway, which might trigger the production of the corresponding DCAs . For biotransformation of methyl decanoate to sebasic acid, addition of decane inducer was controlled to minimize the production of toxic decanoic acid .…”

Section: Resultsmentioning

confidence: 99%

“…More research on the optimization of nonane concentration was done by its addition at the final For a DCA-overproducing Candida maltosa strain, individual addition of n-decane and n-tetradecane induced the expression of the major cytochrome P450 monooxygenases (ALKs) catalyzing the first step of the alkane-assimilation pathway, which might trigger the production of the corresponding DCAs. 30 For biotransformation of methyl decanoate to sebasic acid, addition of decane inducer was controlled to minimize the production of toxic decanoic acid. 22 Finally, it was decided that nonane at the final concentration of 0.2 g/L would be added into the reaction solution before the biotransformation of ENA, MNA, and NA to AZA.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Direct Biotransformation of Nonanoic Acid and Its Esters to Azelaic Acid by Whole Cell Biocatalyst of Candida tropicalis

Kim

Jun

Seong

et al. 2019

ACS Sustainable Chem. Eng.

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Azelaic acid is an α,ω-dicarboxylic acid with nine carbons and has multiple applications in plastic and cosmetic industries. Chemical oxidation of oleic acid with ozone (called ozonolysis) allows the production of azelaic acid and a major byproduct of nonanoic acid. To increase the total yield of azelaic acid in the ozonolysis, in this study, sustainable biotransformation process using a whole cell biocatalyst was developed to directly convert nonanoic acid and its esters to azelaic acid. Candida tropicalis ATCC20962 immediately cleaved ethyl nonanoate to nonanoic acid after ethyl nonanoate addition, and then converted nonanoic acid into azelaic acid with the aid of nonane addition and continuous glucose supply. Finally, a fed-batch biotransformation by continuous feeding of pure nonanoic acid resulted in the production of 30.1 g/L azelaic acid with 0.30 g/L-h productivity and 90% molar yield. By combination of the ozonolysis and our process, a maximum of 95% molar carbon yield of azelaic acid from oleic acid was estimated. This is the first report that nonanoic acid and its esters were directly biotransformed to azelaic acid with over 90% yield, and would be a groundwork for the biotransformation of fatty acids with under nine carbons to the corresponding α,ω-dicarboxylic acids.

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“…DCA conversion is initiated by cytochrome P450 monooxygenase (CYP); members of the CYP family are alkane-inducible in alkane-assimilating yeasts [ 37 – 39 ]. In C. tropicalis , the addition of methyl decanoate without the pre-activation of ω-oxidation resulted in the accumulation of decanoic acid and directly affected cell viability [ 11 ].…”

Section: Resultsmentioning

confidence: 99%

Development of a promising microbial platform for the production of dicarboxylic acids from biorenewable resources

Lee

Han

Lee

et al. 2018

Biotechnol Biofuels

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BackgroundAs a sustainable industrial process, the production of dicarboxylic acids (DCAs), used as precursors of polyamides, polyesters, perfumes, plasticizers, lubricants, and adhesives, from vegetable oil has continuously garnered interest. Although the yeast Candida tropicalis has been used as a host for DCA production, additional strains are continually investigated to meet productivity thresholds and industrial needs. In this regard, the yeast Wickerhamiella sorbophila, a potential candidate strain, has been screened. However, the lack of genetic and physiological information for this uncommon strain is an obstacle that merits further research. To overcome this limitation, we attempted to develop a method to facilitate genetic recombination in this strain and produce high amounts of DCAs from methyl laurate using engineered W. sorbophila.ResultsIn the current study, we first developed efficient genetic engineering tools for the industrial application of W. sorbophila. To increase homologous recombination (HR) efficiency during transformation, the cell cycle of the yeast was synchronized to the S/G2 phase using hydroxyurea. The HR efficiency at POX1 and POX2 loci increased from 56.3% and 41.7%, respectively, to 97.9% in both cases. The original HR efficiency at URA3 and ADE2 loci was nearly 0% during the early stationary and logarithmic phases of growth, and increased to 4.8% and 25.6%, respectively. We used the developed tools to construct W. sorbophila UHP4, in which β-oxidation was completely blocked. The strain produced 92.5 g/l of dodecanedioic acid (DDDA) from methyl laurate over 126 h in 5-l fed-batch fermentation, with a productivity of 0.83 g/l/h.ConclusionsWickerhamiella sorbophila UHP4 produced more DDDA methyl laurate than C. tropicalis. Hence, we demonstrated that W. sorbophila is a powerful microbial platform for vegetable oil-based DCA production. In addition, by using the developed genetic engineering tools, this emerging yeast could be used for the production of a variety of fatty acid derivatives, such as fatty alcohols, fatty aldehydes, and ω-hydroxy fatty acids.Electronic supplementary materialThe online version of this article (10.1186/s13068-018-1310-x) contains supplementary material, which is available to authorized users.

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Enhanced induction of cytochromes P450alk that oxidize methyl-ends of n-alkanes and fatty acids in the long-chain dicarboxylic acid-hyperproducing mutant of Candida maltosa

Cited by 14 publications

References 24 publications

The role of cytochrome P450 monooxygenases in microbial fatty acid metabolism

The role of cytochrome P450 monooxygenases in microbial fatty acid metabolism

Direct Biotransformation of Nonanoic Acid and Its Esters to Azelaic Acid by Whole Cell Biocatalyst of Candida tropicalis

Development of a promising microbial platform for the production of dicarboxylic acids from biorenewable resources

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