Preparative aerobic oxidations with basidiomycetous enzymes: CH-functionalization of adamantane

Zhuk, Tatyana S.; Goldmann, Michael; Hofmann, J. I.; Pohl, Juliane C.S.; Zorn, Holger

doi:10.1016/j.molcatb.2015.08.002

Cited by 11 publications

(2 citation statements)

References 77 publications

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“…In this review, however, we will discuss mainly the processes of oxygenation of carbon-hydrogen bonds to afford compounds with C-O bonds. All hydrocarbon oxidations occurring in living organisms [1,[20][21][22][23][24][25][26][27][28][29] from the mechanistic point of view are also of the second or third types. Some non-organometallic complexes, for example, metal derivatives of porphyrins can play the role of models of certain metal-containing enzyme centers.…”

Section: Introductionmentioning

confidence: 99%

New Trends in Oxidative Functionalization of Carbon–Hydrogen Bonds: A Review

Shul’pin

2016

Catalysts

174

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This review describes new reactions catalyzed by recently discovered types of metal complexes and catalytic systems (catalyst + co-catalyst). Works of recent years (mainly 2010-2016) devoted to the oxygenations of saturated, aromatic hydrocarbons and other carbon-hydrogen compounds are surveyed. Both soluble metal complexes and solid metal compounds catalyze such transformations. Molecular oxygen, hydrogen peroxide, alkyl peroxides, and peroxy acids were used in these reactions as oxidants.

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Section: Introductionmentioning

confidence: 99%

New Trends in Oxidative Functionalization of Carbon–Hydrogen Bonds: A Review

Shul’pin

2016

Catalysts

174

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“…Recently, we discovered the ability of the white-rot fungus D. albidofuscus (DAL) to oxidize adamantane to adamantanol with moderate preparative yields. [14] In the present study, we focused on the oxidation of substituted aromatics and performed labeling studies to get insights into the reaction mechanism. Toluene (1) represents the simplest model compound possessing aromatic and aliphatic carbon atoms.…”

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confidence: 99%

Aerobic C−C Bond Cleavage Catalyzed by Whole‐Cell Cultures of the White‐Rot Fungus Dichomitus albidofuscus

2021

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Whole-cell cultures of the basidiomycetous white-rot fungus Dichomitus albidofuscus exhibit varying catalytic activity towards aromatic compounds depending on the growth stage. This study reveals the catalytic behavior of mature whole-cell cultures that effectively catalyze a CÀ C bond cleavage oxidizing toluene, benzaldehyde and acetophenone to phenol. The reaction products were analyzed by GC-MS and NMR techniques. To exclude the de novo formation of phenol by the fungus, its origin has been proven by bioconversion of benzaldehyde-d 5 . The key step involves an aerobic Baeyer-Villiger type rearrangement where the incorporation of oxygen into the product was confirmed based on isotope labelling experiments with 18 O 2 . Intermediate esters were not found in reaction mixture presumably due to the detected esterase activity in the mycelium as well as in supernatant of the wholecell cultures. As a result, the sequence of biocatalytic reactions catalyzed by D. albidofuscus for the degradation of toluene via CÀ C bond cleavage has been disclosed.

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Mushroom‐Mediated Redox Reactions

Yang

2024

Chemistry A European J

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The application of biocatalysts in organic synthesis has grown significantly in recent years, and both academia and industry are continuously searching for novel biocatalysts capable of performing challenging chemical reactions. Mushroom is a rich source of ligninolytic and secondary metabolite biosynthetic enzymes, and therefore was consider as promising biocatalysts for organic synthesis. This review focused on the broad utilization potential of the mushroom‐based biocatalysts and highlights key advances in mushroom‐mediated organic transformations. It mainly includes reduction of ketone and carboxylic acids, hydroxylation of aromatic and aliphatic compounds, epoxidation of olefin, oxidative cleavage of alkene, and other uncommon reactions catalyzed by the whole‐cells or purified enzymes of mushroom‐origin. Overall, a comprehensive overview of the applications of mushroom as biocatalyst in organic synthesis is provided, which puts this versatile microorganism in the spotlight of further research.

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Preparative aerobic oxidations with basidiomycetous enzymes: CH-functionalization of adamantane

Cited by 11 publications

References 77 publications

New Trends in Oxidative Functionalization of Carbon–Hydrogen Bonds: A Review

New Trends in Oxidative Functionalization of Carbon–Hydrogen Bonds: A Review

Aerobic C−C Bond Cleavage Catalyzed by Whole‐Cell Cultures of the White‐Rot Fungus Dichomitus albidofuscus

Mushroom‐Mediated Redox Reactions

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