A self-sufficient Baeyer–Villiger biocatalysis system for the synthesis of ɛ-caprolactone from cyclohexanol

Mallin, Hendrik; Wulf, H.; Bornscheuer, Uwe T.

doi:10.1016/j.enzmictec.2013.01.007

Cited by 81 publications

(66 citation statements)

References 24 publications

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“…As shown in Table 1, covalent binding is the most common immobilization technique used for immobilization of isolated BVMOs. It is also true that utilization of isolated BVMOs resulted in loss of their enzyme activity despite immobilization (Mallin et al 2013;Cuetos et al 2012;Atia 2005). Moreover, it is not possible to compare results from different immobilization techniques due to inconsistency in choice of characterization parameters for immobilized isolated BVMOs listed in Table 1.…”

Section: Immobilization Of Isolated Bvmosmentioning

confidence: 95%

“…Similarly, reuse of CHMO and alcohol dehydrogenase (ADH) co-immobilized on Eupergit C resulted in progressive decrease of conversion rates after the third cycle of repeated Baeyer-Villiger biooxidations of bicyclo[3.2.0]hept-2-en-6-one (Zambianchi et al 2002). One of the current new routes to enable enzyme recycling and stabilization is represented by coimmobilization of thermostable polyol dehydrogenase (PDH) and CHMO by covalent binding on glutaraldehydeactivated support (Mallin et al 2013). Immobilization enabled production of 600 mg l −1 of pure ε-caprolactone, and CHMO activity towards higher substrate concentrations was improved.…”

Section: Immobilization Of Isolated Bvmosmentioning

confidence: 98%

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Baeyer-Villiger oxidations: biotechnological approach

Bučko

Gemeiner

Schenkmayerová

et al. 2016

Appl Microbiol Biotechnol

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Baeyer-Villiger monooxygenases (BVMOs) are a very well-known and intensively studied class of flavin-dependent enzymes. Their substrate promiscuity, high chemo-, regio-, and enantioselectivity are prerequisites for the use in synthetic chemistry and should pave the way for successful industrial processes. Nonetheless, only a very limited number of industrial relevant transformations are known, mainly due to the lack of BVMOs stability and cofactor dependency. In this review, we focus on novel BVMO-mediated transformations, BVMOs in cascade type reactions, potential industrial applications, and how limitations have been tackled by the community. Special attention will be put on whole-cell immobilization strategies. We emphasize to bridge recent developments in fundamental research to industrial applications.

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Section: Immobilization Of Isolated Bvmosmentioning

confidence: 95%

Section: Immobilization Of Isolated Bvmosmentioning

confidence: 98%

Baeyer-Villiger oxidations: biotechnological approach

Bučko

Gemeiner

Schenkmayerová

et al. 2016

Appl Microbiol Biotechnol

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“…As the biocatalytic approach necessitates nicotinamide cofactors, the use of whole-cells has been of high interest (Alphand and Wohlgemuth, 2010;Alphand et al, 2003;Baldwin et al, 2008;Fink et al, 2011;Law et al, 2006) with the supply of a carbon source to regenerate the cofactor. The self-sufficient linear cascade combining an ADH (Weckbecker and Hummel, 2006) and a cyclohexanone monooxygenase (CHMO) (Donoghue et al, 1976) for the synthesis of ECL makes the biocatalytic route very efficient since only a single substrate ends up to a single final product (Mallin et al, 2013;Scherkus et al, 2016;Schmidt et al, 2015a,b;Staudt et al, 2013). The self-sufficient linear cascade combining an ADH (Weckbecker and Hummel, 2006) and a cyclohexanone monooxygenase (CHMO) (Donoghue et al, 1976) for the synthesis of ECL makes the biocatalytic route very efficient since only a single substrate ends up to a single final product (Mallin et al, 2013;Scherkus et al, 2016;Schmidt et al, 2015a,b;Staudt et al, 2013).…”

Section: Introductionmentioning

confidence: 99%

Kinetic insights into ϵ‐caprolactone synthesis: Improvement of an enzymatic cascade reaction

Scherkus

Schmidt

Bornscheuer

et al. 2017

Biotech & Bioengineering

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A computational approach for the simulation and prediction of a linear three-step enzymatic cascade for the synthesis of e-caprolactone (ECL) coupling an alcohol dehydrogenase (ADH), a cyclohexanone monooxygenase (CHMO), and a lipase for the subsequent hydrolysis of ECL to 6-hydroxyhexanoic acid (6-HHA). A kinetic model was developed with an accuracy of prediction for a fed-batch mode of 37% for substrate cyclohexanol (CHL), 90% for ECL, and >99% for the final product 6-HHA. Due to a severe inhibition of the CHMO by CHL, a batch synthesis was shown to be less efficient than a fed-batch approach. In the fed-batch synthesis, full conversion of 100 mM CHL was 28% faster with an analytical yield of 98% compared to 49% in case of the batch synthesis. The lipase-catalyzed hydrolysis of ECL to 6-HHA circumvents the inhibition of the CHMO by ECL enabling a 24% higher product concentration of 6-HHA compared to ECL in case of the fed-batch synthesis without lipase.

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“…This on-water-obtained cyclohexanol was directly double oxidized into ε-caprolactone (without further isolation step) by means of an alcohol dehydrogenase from Lactobacillus kefir (Lk-ADH) and a cyclohexanone monooxygenase from Acinetobacter sp. NCIMB (CHMO), following a previously-described methodology reported by the authors [67,68]. At this point, it is worth noting that: (i) both enzymes just required O2 as oxidizing reagent (avoiding co-catalysts); and (ii) the desired ε-caprolactone was obtained in 90% yield after 24 h of reaction.…”

Section: Combination Of Rh-catalyzed Hydrogenation Of Phenol Double mentioning

confidence: 99%

One-Pot Combination of Metal- and Bio-Catalysis in Water for the Synthesis of Chiral Molecules

2018

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During the last decade, the combination of different metal-and bio-catalyzed organic reactions in aqueous media has permitted the flourishing of a variety of one-pot asymmetric multi-catalytic reactions devoted to the construction of enantiopure and high added-value chemicals under mild reaction conditions (usually room temperature) and in the presence of air. Herein, a comprehensive account of the state-of-the-art in the development of catalytic networks by combining metallic and biological catalysts in aqueous media (the natural environment of enzymes) is presented. Among others, the combination of metal-catalyzed isomerizations, cycloadditions, hydrations, olefin metathesis, oxidations, C-C cross-coupling and hydrogenation reactions, with several biocatalyzed transformations of organic groups (enzymatic reduction, epoxidation, halogenation or ester hydrolysis), are discussed.

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A self-sufficient Baeyer–Villiger biocatalysis system for the synthesis of ɛ-caprolactone from cyclohexanol

Cited by 81 publications

References 24 publications

Baeyer-Villiger oxidations: biotechnological approach

Baeyer-Villiger oxidations: biotechnological approach

Kinetic insights into ϵ‐caprolactone synthesis: Improvement of an enzymatic cascade reaction

One-Pot Combination of Metal- and Bio-Catalysis in Water for the Synthesis of Chiral Molecules

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