Simultaneous Enzyme/Whole‐Cell Biotransformation of C18 Ricinoleic Acid into (<i>R</i>)‐3‐Hydroxynonanoic Acid, 9‐Hydroxynonanoic Acid, and 1,9‐Nonanedioic Acid

Cha, Hee-Jeong; Seo, Eun-Ji; Song, Ji‐Won; Jo, Hye-Jin; Akula, Ravi Kumar; Park, Jin Byung

doi:10.1002/adsc.201701029

Cited by 35 publications

(24 citation statements)

References 38 publications

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“…According to previous reports 54,55 and our experience, the bottleneck in the above cascades is likely the Baeyer-Villiger oxidation by PfBVMO (for 4b) and PpBVMO (for 4a). Some Nterminal tags on BVMOs have been shown to improve the stability of the enzymes 60 .…”

Section: From 3csupporting

confidence: 69%

“…Subjecting the keto-acid to a Baeyer-Villiger monooxygenase, using either PpBVMO or PfBVMO, followed by hydrolysis by TLL affords either sebacic acid (4b) -with PfBVMO-or a hydroxy-carboxylic acid -with PpBVMO-. The latter may be oxidized by ChnD and ChnE to afford azelaic acid (4a) 55 (Fig. 2b, Supplementary Fig.…”

Section: Resultsmentioning

confidence: 99%

“…To produce cyclopentene (1a) and cyclohexene (1b) from oleic acid (6), it is necessary to engineer enzyme cascades to produce the corresponding sebacic acid (4b) and azelaic acid (4a) from oleic acid (6). Two previous enzyme cascades 54 have reported the conversion of oleic acid (6) to diacids 4a and 4b via hydration, oxidation, Baeyer-Villiger oxidation (with different regioselectivity) and hydrolysis by TLL (for 4b), as well as further double oxidation (for 4a) 55 (Fig. 2b, Supplementary Fig.…”

Section: From 3cmentioning

confidence: 99%

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Chemo-enzymatic cascades to produce cycloalkenes from bio-based resources

Zhou

Gerngross

et al. 2019

Nat Commun

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Engineered enzyme cascades offer powerful tools to convert renewable resources into valueadded products. Man-made catalysts give access to new-to-nature reactivities that may complement the enzyme's repertoire. Their mutual incompatibility, however, challenges their integration into concurrent chemo-enzymatic cascades. Herein we show that compartmentalization of complex enzyme cascades within E. coli whole cells enables the simultaneous use of a metathesis catalyst, thus allowing the sustainable one-pot production of cycloalkenes from oleic acid. Cycloheptene is produced from oleic acid via a concurrent enzymatic oxidative decarboxylation and ring-closing metathesis. Cyclohexene and cyclopentene are produced from oleic acid via either a six-or eight-step enzyme cascade involving hydration, oxidation, hydrolysis and decarboxylation, followed by ring-closing metathesis. Integration of an upstream hydrolase enables the usage of olive oil as the substrate for the production of cycloalkenes. This work highlights the potential of integrating organometallic catalysis with whole-cell enzyme cascades of high complexity to enable sustainable chemistry.

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Section: From 3csupporting

confidence: 69%

Section: Resultsmentioning

confidence: 99%

Section: From 3cmentioning

confidence: 99%

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Chemo-enzymatic cascades to produce cycloalkenes from bio-based resources

Zhou

Gerngross

et al. 2019

Nat Commun

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“…In the initial step, a plant oil is hydrolyzed, and the final step consists of the hydrolysis of the ester by the means of a lipase from Thermomyces lanuginosus. The ω-hydroxycarboxylic acid is then further derivatized by means of chemical [64] or enzymatic oxidation, and the resulting product can then further be used as a monomer for the production of polyesters and polyamides [73]. This synthetic method was further extended towards a process based on the use of a whole cell catalyst, which converts long chain fatty acids like ricinoleic acid, in combination with an added aldehyde dehydrogenase, in order to obtain the corresponding ω-hydroxycarboxylic acid (Figure 4) [74].…”

Section: Cascade Processes Involving Fatty Acid Hydratasementioning

confidence: 99%

Fatty Acid Hydratases: Versatile Catalysts to Access Hydroxy Fatty Acids in Efficient Syntheses of Industrial Interest

Löwe

Gröger

2020

Catalysts

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The utilization of hydroxy fatty acids has gained more and more attention due to its applicability in many industrial building blocks that require it, for example, polymers or fragrances. Furthermore, hydroxy fatty acids are accessible from biorenewables, thus contributing to a more sustainable raw material basis for industrial chemicals. Therefore, a range of investigations were done on fatty acid hydratases (FAHs), since these enzymes catalyze the addition of water to an unsaturated fatty acid, thus providing an elegant route towards hydroxy-substituted fatty acids. Besides the discovery and characterization of fatty acid hydratases (FAHs), the design and optimization of syntheses with these enzymes, the implementation in elaborate cascades, and the improvement of these biocatalysts, by way of mutation in terms of the substrate scope, has been investigated. This mini-review focuses on the research done on process development using fatty acid hydratases as a catalyst. It is notable that biotransformations, running at impressive substrate loadings of up to 280 g L−1, have been realized. A further topic of this mini-review is the implementation of fatty acid hydratases in cascade reactions. In such cascades, fatty acid hydratases were, in particular, combined with alcohol dehydrogenases (ADH), Baeyer-Villiger monooxygenases (BVMO), transaminases (TA) and hydrolases, thus enabling access to a broad variety of molecules that are of industrial interest.

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“…Then the hydrolysis product entered back into the E. coli cells and was further oxidized to 1,9‐nonanedionic acid by ChnDE. Preparative‐scale reaction (200 mL) afforded 3‐hydroxynonanoic acid and 1,9‐nonanedionic acid with 80 % conversion and isolated yields of 63 % and 64 %, respectively after purification by column chromatography …”

Section: Hybrid In Vitro and In Vivo Cascadesmentioning

confidence: 99%

Extending Designed Linear Biocatalytic Cascades for Organic Synthesis

2018

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Artificial cascade reactions involving biocatalysts have demonstrated a tremendous potential during the recent years. This review just focuses on selected examples of the last year and putting them into context to a previously published suggestion for classification. Subdividing the cascades according to the number of catalysts in the linear sequence, and classifying whether the steps are performed simultaneous or in a sequential fashion as well as whether the reaction sequence is performed in vitro or in vivo allows to organise the concepts. The last year showed, that combinations of in vivo as well as in vitro are possible. Incompatible reaction steps may be run in a sequential fashion or by compartmentalisation of the incompatible steps either by using special reactors (membrane), polymersomes or flow techniques.

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Simultaneous Enzyme/Whole‐Cell Biotransformation of C18 Ricinoleic Acid into (R)‐3‐Hydroxynonanoic Acid, 9‐Hydroxynonanoic Acid, and 1,9‐Nonanedioic Acid

Cited by 35 publications

References 38 publications

Chemo-enzymatic cascades to produce cycloalkenes from bio-based resources

Chemo-enzymatic cascades to produce cycloalkenes from bio-based resources

Fatty Acid Hydratases: Versatile Catalysts to Access Hydroxy Fatty Acids in Efficient Syntheses of Industrial Interest

Extending Designed Linear Biocatalytic Cascades for Organic Synthesis

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