Efficient Synthesis of Methyl 3-Acetoxypropionate by a Newly Identified Baeyer-Villiger Monooxygenase

Liu, Yuanyang; Li, Chun-Xiu; Xu, Jian‐He; Zheng, Gao‐Wei

doi:10.1128/aem.00239-19

Cited by 7 publications

(6 citation statements)

References 54 publications

(54 reference statements)

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“…218,219 The latest example is a BVMO from Rhodoccocus pyridinivorans DSM 44555. 189 RpBVMO exhibited affinity for aliphatic methyl ketones and the highest activity on 2-hexanone (k cat = 2 s −1 ). RpBVMO was able to regioselectively convert hexanones, octanones, and methyl levulinate.…”

Section: T H I S C O N T E N T Imentioning

confidence: 99%

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Baeyer–Villiger Monooxygenases: Tunable Oxidative Biocatalysts

et al. 2019

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Pollution, accidents, and misinformation have earned the pharmaceutical and chemical industry a poor public reputation, despite their undisputable importance to society. Biotechnological advances hold the promise to enable a future of drastically reduced environmental impact and rigorously more efficient production routes at the same time. This is exemplified in the Baeyer–Villiger reaction, which offers a simple synthetic route to oxidize ketones to esters, but application is hampered by the requirement of hazardous and dangerous reagents. As an attractive alternative, flavin-containing Baeyer–Villiger monooxygenases (BVMOs) have been investigated for their potential as biocatalysts for a long time, and many variants have been characterized. After a general look at the state of biotechnology, we here summarize the literature on biochemical characterizations, mechanistic and structural investigations, as well as enzyme engineering efforts in BVMOs. With a focus on recent developments, we critically outline the advances toward tuning these enzymes suitable for industrial applications.

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Section: T H I S C O N T E N T Imentioning

confidence: 99%

“…The latest example is a BVMO from Rhodoccocus pyridinivoran s DSM 44555 . RpBVMO exhibited affinity for aliphatic methyl ketones and the highest activity on 2-hexanone ( k cat = 2 s –1 ).…”

Section: Variety Of Bvmosmentioning

confidence: 99%

Baeyer–Villiger Monooxygenases: Tunable Oxidative Biocatalysts

et al. 2019

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“…The preparation of Ac PSMO and Bst FDH combi-CLEAs was optimized for the synthesis of esomeprazole. Tm CHMO and BVMO from Rhodococcus pyridinivorans ( Rp BVMO) were also chosen to be coimmobilized with Bst FDH for use in the repeated cyclohexanone oxygenation reaction.…”

Section: Introductionmentioning

confidence: 99%

Co-Cross-Linked Aggregates of Baeyer–Villiger Monooxygenases and Formate Dehydrogenase for Repeated Use in Asymmetric Biooxidation

Zhu

Geng

Liu

et al. 2022

Org. Process Res. Dev.

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Baeyer−Villiger monooxygenases (BVMOs) are versatile biocatalysts, but their applications are hindered by their poor stability and cofactor dependence. In this study, cross-linked enzyme aggregate (CLEA) technology was adopted to coimmobilize BVMO and its accessory cofactor-regeneration enzyme. Combi-CLEAs of a pyrmetazole monooxygenase from Acinetobacter calcoaceticus (AcPSMO) and a formate dehydrogenase from Burkholderia stabili (BstFDH) were prepared for the synthesis of (S)-omeprazole. After optimization, AcPSMO and BstFDH were coprecipitated with an activity ratio of 1:6 using ammonium sulfate and then cross-linked with glutaraldehyde (0.12% w/v). The activity recoveries of AcPSMO and BstFDH in the prepared combi-CLEAs were 43% and 38%, respectively. Compared with the free enzymes AcPSMO and BstFDH, the thermostabilities of AcPSMO and BstFDH in combi-CLEAs were improved by 2.5-and 1.6-fold, respectively. Both enzymes were more stable against alkaline buffer after being immobilized. The combi-CLEAs could be reused for seven cycles in the biooxidative synthesis of (S)-omeprazole without significant activity loss, indicating the excellent operational stability and reusability in repeated reactions for the enzymatic synthesis of (S)-omeprazole. Another two combi-CLEAs prepared under the same conditions, TmCHMO−BstFDH and RpBVMO−BstFDH, can be reused for at least 15 consecutive batches for the cyclohexanone monooxygenation reaction, which indicates the promising potential for coimmobilization of BVMOs and FDH with CLEA methodology.

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“…Dalcin Martins, Frank, Mitchell, Markillie, and Wilkins (2019) applied metagenomic and metatranscriptomic tools to identify novel genes and pathways and microorganisms producing alcohol in wetland prairie pothole sediments (Dalcin Martins et al, 2019). Liu, Li, Xu, and Zheng (2019) studied the bioconversion of ketones to esters and lactones using Baeyer–Villiger monoxygenases (BVMOs) from Rhodococcus pyridinivorans .…”

Section: Bacteriamentioning

confidence: 99%

Substratum‐associated microbiota

Furey

Lee

Clemans

2020

Water Environment Research

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Highlights of new, interesting, and emerging research findings on substratum-associated microbiota covered from a survey of 2019 literature from primarily freshwaters provide insight into research trends of interest to the Water Environment Federation and others interested in benthic, aquatic environments. Coverage of topics on bottom-associated or attached algae and cyanobacteria, though not comprehensive, includes new methods, taxa new-to-science, nutrient dynamics, auto-and heterotrophic interactions, grazers, bioassessment, herbicides and other pollutants, metal contaminants, and nuisance, and bloom-forming and harmful algae. Coverage of bacteria, also not comprehensive, focuses on the ecology of benthic biofilms and microbial communities, along with the ecology of microbes like Caulobacter crescentus, Rhodobacter, and other freshwater microbial species. Bacterial topics covered also include metagenomics and metatranscriptomics, toxins and pollutants, bacterial pathogens and bacteriophages, and bacterial physiology. Readers may use this literature review to learn about or renew their interest in the recent advances and discoveries regarding substratum-associated microbiota. © 2020 Water Environment Federation • Practitioner points • This review of literature from 2019 on substratum-associated microbiota presents highlights of findings on algae, cyanobacteria, and bacteria from primarily freshwaters. • Coverage of algae and cyanobacteria includes findings on new methods, taxa new to science, nutrient dynamics, auto-and heterotrophic interactions, grazers, bioassessment, herbicides and other pollutants, metal contaminants, and nuisance, bloomforming and harmful algae. • Coverage of bacteria includes findings on ecology of benthic biofilms and microbial communities, the ecology of microbes, metagenomics and metatranscriptomics, toxins and pollutants, bacterial pathogens and bacteriophages, and bacterial physiology. • Highlights of new, noteworthy and emerging topics build on those from 2018 and will be of relevance to the Water Environment Federation and others interested in benthic, aquatic environments

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Efficient Synthesis of Methyl 3-Acetoxypropionate by a Newly Identified Baeyer-Villiger Monooxygenase

Cited by 7 publications

References 54 publications

Baeyer–Villiger Monooxygenases: Tunable Oxidative Biocatalysts

Baeyer–Villiger Monooxygenases: Tunable Oxidative Biocatalysts

Co-Cross-Linked Aggregates of Baeyer–Villiger Monooxygenases and Formate Dehydrogenase for Repeated Use in Asymmetric Biooxidation

Substratum‐associated microbiota

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