Enzyme/whole-cell biotransformation of plant oils, yeast derived oils, and microalgae fatty acid methyl esters into n-nonanoic acid, 9-hydroxynonanoic acid, and 1,9-nonanedioic acid

Seo, Eun Ji; Yeon, Young Joo; Seo, Joo Hyun; Lee, Jung Hoo; Boñgol, Jhoanne P.; Oh, Yuri; Park, Jong; Lim, Sang Min; Lee, Choul‐Gyun; Park, Jin Byung

doi:10.1016/j.biortech.2017.12.036

Cited by 61 publications

(61 citation statements)

References 25 publications

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“…LrOhyA catalysed the hydration of oleic acid ( Supplementary Fig. 6) followed by CvFAP-catalysed decarboxylation of the intermediate For example: a hydrolase-catalysed esterification of amidation 4 , b reductase-catalysed reduction of the carboxylate group to the corresponding aldehyde and alcohol 30,31 , c P450-peroxygenase-catalysed oxidative decarboxylation yielding terminal alkenes [5][6][7] , d photodecarboxylase-catalysed decarboxylation yielding alkanes 38,39 , e hydratase-catalysed water addition to C=C-bonds 50 , f lipoxygenase-catalysed allylic hydroperoxidation 21 , g use of mono-, di-and per-oxygenases for the terminal hydroxylation and further transformation into acids or amines as polymer building blocks [15][16][17][18]51 , and h multi-enzyme cascades yielding short-chain acids [22][23][24][25][26][27] .…”

Section: Resultsmentioning

confidence: 99%

“…The resulting hydroxy acids may be interesting building blocks for biobased and biodegradable polyesters. Oxyfunctionalisation of unsaturated fatty acids can also be achieved via selective water addition to the cis-C=Cdouble bond 19,20 or via allylic hydroperoxidation 21 followed by C-C-bond cleavage [22][23][24][25][26][27] or isomerisation to diols 28,29 . Also the selective reduction of the carboxylate group to either the alcohol or aldehyde moiety is possible 30,31 .…”

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confidence: 99%

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Photobiocatalytic synthesis of chiral secondary fatty alcohols from renewable unsaturated fatty acids

et al. 2020

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En route to a bio-based chemical industry, the conversion of fatty acids into building blocks is of particular interest. Enzymatic routes, occurring under mild conditions and excelling by intrinsic selectivity, are particularly attractive. Here we report photoenzymatic cascade reactions to transform unsaturated fatty acids into enantiomerically pure secondary fatty alcohols. In a first step the C=C-double bond is stereoselectively hydrated using oleate hydratases from Lactobacillus reuteri or Stenotrophomonas maltophilia. Also, dihydroxylation mediated by the 5,8-diol synthase from Aspergillus nidulans is demonstrated. The second step comprises decarboxylation of the intermediate hydroxy acids by the photoactivated decarboxylase from Chlorella variabilis NC64A. A broad range of (poly)unsaturated fatty acids can be transformed into enantiomerically pure fatty alcohols in a simple one-pot approach.

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Section: Resultsmentioning

confidence: 99%

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confidence: 99%

Photobiocatalytic synthesis of chiral secondary fatty alcohols from renewable unsaturated fatty acids

et al. 2020

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“…HI-31 31 and alcohol dehydrogenase (ADH2) and aldehyde dehydrogenase (ALDH) from Acinetobacter sp. NCIMB9871 32,33 . To provide sufficient NAD + cofactor, NADH oxidase (NOX) originating from Lactobacillus brevis DSM 20054 was employed 34 .…”

Section: Resultsmentioning

confidence: 99%

One-pot biocatalytic route from cycloalkanes to α,ω‐dicarboxylic acids by designed Escherichia coli consortia

Wang

Zhao

et al. 2020

Nat Commun

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Aliphatic α,ω‐dicarboxylic acids (DCAs) are a class of useful chemicals that are currently produced by energy-intensive, multistage chemical oxidations that are hazardous to the environment. Therefore, the development of environmentally friendly, safe, neutral routes to DCAs is important. We report an in vivo artificially designed biocatalytic cascade process for biotransformation of cycloalkanes to DCAs. To reduce protein expression burden and redox constraints caused by multi-enzyme expression in a single microbe, the biocatalytic pathway is divided into three basic Escherichia coli cell modules. The modules possess either redox-neutral or redox-regeneration systems and are combined to form E. coli consortia for use in biotransformations. The designed consortia of E. coli containing the modules efficiently convert cycloalkanes or cycloalkanols to DCAs without addition of exogenous coenzymes. Thus, this developed biocatalytic process provides a promising alternative to the current industrial process for manufacturing DCAs.

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“…coli BL21(DE3) strains, expressing the cascade enzymes including the engineered Baeyer-Villiger monooxygenases (i.e., E6BVMO and E6BVMO C302L ) of P . putida KT2440 (Scheme S1) were cultivated overnight in the lysogeny broth (LB) medium supplemented with appropriate antibiotics (Table S1 ) for seed cultivation 64 . The Riesenberg medium supplemented with 10 g/L glucose and the appropriate antibiotics was used for the main cultivation and biotransformation.…”

Section: Methodsmentioning

confidence: 99%

Improving catalytic activity of the Baeyer–Villiger monooxygenase-based Escherichia coli biocatalysts for the overproduction of (Z)-11-(heptanoyloxy)undec-9-enoic acid from ricinoleic acid

Woo

Jeon

Seo

et al. 2018

Sci Rep

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Baeyer–Villiger monooxygenases (BVMOs) can be used for the biosynthesis of lactones and esters from ketones. However, the BVMO-based biocatalysts are not so stable under process conditions. Thereby, this study focused on enhancing stability of the BVMO-based biocatalysts. The biotransformation of ricinoleic acid into (Z)-11-(heptanoyloxy)undec-9-enoic acid by the recombinant Escherichia coli expressing the BVMO from Pseudomonas putida and an alcohol dehydrogenase from Micrococcus luteus was used as a model system. After thorough investigation of the key factors to influence stability of the BVMO, Cys302 was identified as an engineering target. The substitution of Cys302 to Leu enabled the engineered enzyme (i.e., E6BVMOC302L) to become more stable toward oxidative and thermal stresses. The catalytic activity of E6BVMOC302L-based E. coli biocatalysts was also greater than the E6BVMO-based biocatalysts. Another factor to influence biocatalytic performance of the BVMO-based whole-cell biocatalysts was availability of carbon and energy source during biotransformations. Glucose feeding into the reaction medium led to a marked increase of final product concentrations. Overall, the bioprocess engineering to improve metabolic stability of host cells in addition to the BVMO engineering allowed us to produce (Z)-11-(heptanoyloxy)undec-9-enoic acid to a concentration of 132 mM (41 g/L) from 150 mM ricinoleic acid within 8 h.

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Enzyme/whole-cell biotransformation of plant oils, yeast derived oils, and microalgae fatty acid methyl esters into n-nonanoic acid, 9-hydroxynonanoic acid, and 1,9-nonanedioic acid

Cited by 61 publications

References 25 publications

Photobiocatalytic synthesis of chiral secondary fatty alcohols from renewable unsaturated fatty acids

Photobiocatalytic synthesis of chiral secondary fatty alcohols from renewable unsaturated fatty acids

One-pot biocatalytic route from cycloalkanes to α,ω‐dicarboxylic acids by designed Escherichia coli consortia

Improving catalytic activity of the Baeyer–Villiger monooxygenase-based Escherichia coli biocatalysts for the overproduction of (Z)-11-(heptanoyloxy)undec-9-enoic acid from ricinoleic acid

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