Direktoxidation von Cycloalkanen zu Cycloalkanonen mit Sauerstoff in Wasser

Staudt, Svenja; Burda, Edyta; Giese, Carolin; Müller, Christina; Marienhagen, Jan; Schwaneberg, Ulrich; Hummel, Werner; Drauz, Karlheinz; Gröger, Harald

doi:10.1002/ange.201204464

Cited by 21 publications

(6 citation statements)

References 30 publications

(21 reference statements)

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“…According to Ikenaga, the selectivity of the conversion of camphor to 1,7,7‐trimethyl‐bicyclo[2.2.1]heptan‐2‐amine ( 7 ) compared to 1,7,7‐trimethyl‐bicyclo[2.2.1]heptan‐2‐ol ( 8 ; Scheme ) is influenced by the addition of ammonium chloride to the reaction mixture 31. The catalysts described in this paper are ruthenium on carbon and palladium on carbon, which both show a good selectivity to amine 8 in the presence of ammonium chloride.…”

Section: Resultsmentioning

confidence: 99%

“…In our procedures, however, the cell‐free enzyme cascade works very well and, by combining two reactions in one pot (hydroxylation and oxidation), even an increased yield of the initial hydroxylation can be obtained compared to previously published results, owing to decreased decoupling. Recently, Gröger and coworkers have been able to use a similar system of combining a P450 monooxygenase and alcohol dehydrogenase to produce cycloalkanones without requiring exogenous substrates 31…”

Section: Discussionmentioning

confidence: 99%

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Biocatalytic Synthesis of a Diketobornane as a Building Block for Bifunctional Camphor Derivatives

2013

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Camphor is a natural terpene readily available in huge amounts with the potential to replace existing chemical compounds derived from fossil resources. To create new industrial applications of camphor, it is necessary to introduce additional functional groups into its non‐reactive carbohydrate backbone. With the P450cam enzyme system of Pseudomonas putida, it is possible to selectively oxidize the non‐activated C5 position of camphor with air under mild conditions to produce 5‐exo‐hydroxycamphor. In this study, the dehydrogenase enzyme that catalyzes the further oxidation of 5‐exo‐hydroxycamphor to the diketone derivative (FdeH) has been cloned and analyzed. Together with the P450cam enzyme system, FdeH was used to realize a cell‐free enzymatic cascade reaction producing 2,5‐diketobornane at the lab scale. We show that this process is highly efficient in terms of NADH cofactor usage and reaction yield. The enzymatically produced 2,5‐diketobornane was converted further into corresponding biobased diamine and diol compounds. Our results show the advantage of combining enzymatic and chemical catalytic synthesis for the development of new routes to novel terpene‐based bicyclic bifunctional derivatives.

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Section: Resultsmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Biocatalytic Synthesis of a Diketobornane as a Building Block for Bifunctional Camphor Derivatives

2013

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“…The group selected two P450 BM3 mutants through screening studies, and an ADH from Lactobacillus kefir to perform double oxidation on inert substrates cyclohexane, cyclooctane and cyclodecane. Additionally, the group used the oxidised cofactor NADP+ which was reduced to NADPH by ADH using 2‐propanol as a sacrificial substrate, to initiate the reaction (Figure 9A) [201] . Urlacher et al.…”

Section: Applications Of Oxygenating Biocatalysts In Drug Discovery A...mentioning

confidence: 99%

“…Gröger et al. have used the P450‐ADH cascade for the direct conversion of cycloalkanes to the corresponding ketones [201] . The group selected two P450 BM3 mutants through screening studies, and an ADH from Lactobacillus kefir to perform double oxidation on inert substrates cyclohexane, cyclooctane and cyclodecane.…”

Section: Applications Of Oxygenating Biocatalysts In Drug Discovery A...mentioning

confidence: 99%

Oxygenating Biocatalysts for Hydroxyl Functionalisation in Drug Discovery and Development

Charlton

Hayes

2022

ChemMedChem

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CÀ H oxyfunctionalisation remains a distinct challenge for synthetic organic chemists. Oxygenases and peroxygenases (grouped here as "oxygenating biocatalysts") catalyse the oxidation of a substrate with molecular oxygen or hydrogen peroxide as oxidant. The application of oxygenating biocatalysts in organic synthesis has dramatically increased over the last decade, producing complex compounds with potential uses in the pharmaceutical industry. This review will focus on hydroxyl functionalisation using oxygenating biocatalysts as a tool for drug discovery and development. Established oxygenating biocatalysts, such as cytochrome P450s and flavin-dependent monooxygenases, have widely been adopted for this purpose, but can suffer from low activity, instability or limited substrate scope. Therefore, emerging oxygenating biocatalysts which offer an alternative will also be covered, as well as considering the ways in which these hydroxylation biotransformations can be applied in drug discovery and development, such as latestage functionalisation (LSF) and in biocatalytic cascades.

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“…ADH-catalysed oxidations also play a key role in various multi-step cascades valorising simple starting materials into more complex products. For example, monooxygenasecatalysed hydroxylation reactions of non-functionalised C-Hbonds yield alcohols that can further be converted into the corresponding ketones (Figure 24A) (Müller et al, 2013;Staudt et al, 2013;Tavanti et al, 2017a;Tavanti et al, 2017b). Similarly, starting from alcohols, redox-neutral ADHmonooxygenase cascades producing lactones are possible (Figure 24B) (Schmidt et al, 2015a;Schmidt et al, 2015b;Scherkus et al, 2016;Scherkus et al, 2017;Wedde et al, 2017).…”

Section: Adh-catalysed Oxidation Reactionsmentioning

confidence: 99%

Alcohol Dehydrogenases as Catalysts in Organic Synthesis

2022

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Alcohol dehydrogenases (ADHs) have become important catalysts for stereoselective oxidation and reduction reactions of alcohols, aldehydes and ketones. The aim of this contribution is to provide the reader with a timely update on the state-of-the-art of ADH-catalysis. Mechanistic basics are presented together with practical information about the use of ADHs. Current concepts of ADH engineering and ADH reactions are critically discussed. Finally, this contribution highlights some prominent examples and future-pointing concepts.

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Direktoxidation von Cycloalkanen zu Cycloalkanonen mit Sauerstoff in Wasser

Cited by 21 publications

References 30 publications

Biocatalytic Synthesis of a Diketobornane as a Building Block for Bifunctional Camphor Derivatives

Biocatalytic Synthesis of a Diketobornane as a Building Block for Bifunctional Camphor Derivatives

Oxygenating Biocatalysts for Hydroxyl Functionalisation in Drug Discovery and Development

Alcohol Dehydrogenases as Catalysts in Organic Synthesis

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