A Horseradish Peroxidase-Mediator System for Benzylic C-H Activation

Article Biochemistry & Molecular Biology

A Peroxygenase-Alcohol Dehydrogenase Cascade Reaction to Transform Ethylbenzene Derivatives into Enantioenriched Phenylethanols

Xiaomin Xu et al.

Summary: In this study, a new enzymatic reaction was developed to produce enantioenriched phenylethanols. By using a two-step cascade reaction, eleven ethylbenzene derivatives were converted into chiral alcohols with high enantioselectivity.

CHEMBIOCHEM (2022)

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Article Chemistry, Multidisciplinary

Electrochemical Activation of C-C Bonds through Mediated Hydrogen Atom Transfer Reactions

Bing Yan et al.

Summary: This study uses redox mediators to activate inert C-C bonds and achieve the chemical upcycling of polyolefin waste. It is found that the selectivity of C-C bond cleavage increases with decreasing C-C bond dissociation energy. With NHPI-mediated oxidation, oligomeric styrene and polystyrene can be converted into oxygenated oligomers.

CHEMSUSCHEM (2022)

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Review Biochemistry & Molecular Biology

Harnessing P450 Enzyme for Biotechnology and Synthetic Biology

Libo Zhang et al.

Summary: Cytochrome P450 enzymes play a crucial role in the oxidative transformation of organic substrates, but face limitations in synthetic biology applications. Recent research has focused on emerging strategies such as substrate engineering, decoy-based auxiliaries, and designing artificial enzyme cascades to improve P450 enzyme activity. Remaining challenges and future opportunities will be discussed in this minireview.

CHEMBIOCHEM (2022)

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Article Chemistry, Multidisciplinary

Site-Selective Electrochemical Benzylic C-H Amination

Zhong-Wei Hou et al.

Summary: This study reports a site-selective electrochemical amination reaction that can convert benzylic C-H bonds into C-N linkages without the need for external oxidants or metal catalysts. The success lies in using HFIP as a co-solvent to modulate the oxidation potentials of the substrate and product, avoiding overoxidation of the latter.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

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Article Chemistry, Multidisciplinary

DNA-Scaffolded Synergistic Catalysis

Edward B. Pimentel et al.

Summary: This study demonstrates that DNA-scaffolded catalysis can increase the turnover number of catalysts and control the rate of synergistic catalytic reactions. This concept opens new avenues for future research in reaction discovery, sensing, responsive materials, and chemical biology.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

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Article Multidisciplinary Sciences

Benzylic C-H acylation by cooperative NHC and photoredox catalysis

Qing-Yuan Meng et al.

Summary: Methods enabling site-selective acylation of sp3 C-H bonds in complex organic molecules are not well explored. Here, the authors present a direct and site-selective acylation of benzylic C-H bonds through the combination of N-heterocyclic carbene (NHC) and photoredox catalysis, offering options for preparing benzyl aryl ketones.

NATURE COMMUNICATIONS (2021)

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Article Chemistry, Multidisciplinary

A donor-acceptor complex enables the synthesis of E-olefins from alcohols, amines and carboxylic acids

Kun-Quan Chen et al.

Summary: The novel strategy for the selective synthesis of olefins presented in this study utilizes EDA complexes, eliminating the need for transition metal catalysts and photocatalysts. The method is operationally simple, straightforward, shows high regio- and stereoselectivities, and allows for the synthesis of olefins from easily available starting materials.

CHEMICAL SCIENCE (2021)

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Review Chemistry, Multidisciplinary

Electrochemical Oxidation of Organic Molecules at Lower Overpotential: Accessing Broader Functional Group Compatibility with Electron-Proton Transfer Mediators

Fei Wang et al.

ACCOUNTS OF CHEMICAL RESEARCH (2020)

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Article Chemistry, Organic

Enantiocomplementary C-H Bond Hydroxylation Combining Photo-Catalysis and Whole-Cell Biocatalysis in a One-Pot Cascade Process

Yongzhen Peng et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2020)

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Article Chemistry, Multidisciplinary

Enantioselective Hydroxylation of Benzylic C(sp3)-H Bonds by an Artificial Iron Hydroxylase Based on the Biotin-Streptavidin Technology

Joan Serrano-Plana et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

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Article Chemistry, Physical

Increasing Redox Potential, Redox Mediator Activity, and Stability in a Fungal Laccase by Computer-Guided Mutagenesis and Directed Evolution

Ivan Mateljak et al.

ACS CATALYSIS (2019)

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Article Chemistry, Multidisciplinary

Combined Photoredox/Enzymatic C-H Benzylic Hydroxylations

Rick C. Betori et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

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Article Biotechnology & Applied Microbiology

LC-MSMS based screening of emerging pollutant degradation by different peroxidases

Khadega A. Almaqdi et al.

BMC BIOTECHNOLOGY (2019)

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Article Multidisciplinary Sciences

A chemo-enzymatic oxidation cascade to activate C-H bonds with in situ generated H2O2

Simon J. Freakley et al.

NATURE COMMUNICATIONS (2019)

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Article Chemistry, Organic

Combining Photo-Organo Redox- and Enzyme Catalysis Facilitates Asymmetric C-H Bond Functionalization

Wuyuan Zhang et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2019)

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Article Chemistry, Organic

Selective Phthalimido- N -oxyl (PINO)-Catalyzed C-H Cyanation of Adamantane Derivatives

Jan-Philipp Berndt et al.

SYNLETT (2019)

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Article Chemistry, Organic

N-Hydroxyphthalimide/benzoquinone-catalyzed chlorination of hydrocarbon C-H bond using N-chlorosuccinimide

Zi-Hao Li et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2019)

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Article Chemistry, Multidisciplinary

&ITN&IT-Hydroxyphthalimide-Mediated Electrochemical Iodination of Methylarenes and Comparison to Electron-Transfer-Initiated C-H Functionalization

Mohammad Rafiee et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2018)

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Review Chemistry, Multidisciplinary

Tetramethylpiperidine N-Oxyl (TEMPO), Phthalimide N-Oxyl (PINO), and Related N-Oxyl Species: Electrochemical Properties and Their Use in Electrocatalytic Reactions

Jordan E. Nutting et al.

CHEMICAL REVIEWS (2018)

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Article Chemistry, Multidisciplinary

Continuous N-Hydroxyphthalimide (NHPI)-Mediated Electrochemical Aerobic Oxidation of Benzylic C-H Bonds

Yiming Mo et al.

CHEMISTRY-A EUROPEAN JOURNAL (2018)

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Article Chemistry, Multidisciplinary

Combined Iron/Hydroxytriazole Dual Catalytic System for Site Selective Oxidation Adjacent to Azaheterocycles

Julian C. Cooper et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2018)

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Article Chemistry, Multidisciplinary

Generation and Confinement of Long-Lived N-Oxyl Radical and Its Photocatalysis

Chaofeng Zhang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2018)

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Article Chemistry, Multidisciplinary

Manganese-catalysed benzylic C(sp(3))-H amination for late-stage functionalization

Joseph R. Clark et al.

NATURE CHEMISTRY (2018)

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Article Chemistry, Multidisciplinary

Intermolecular Radical Mediated Anti-Markovnikov Alkene Hydroamination Using N-Hydroxyphthalimide

Samuel W. Lardy et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2018)

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Article Chemistry, Physical

Selective aerobic oxidation reactions using a combination of photocatalytic water oxidation and enzymatic oxyfunctionalizations

Wuyuan Zhang et al.

NATURE CATALYSIS (2018)

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Article Chemistry, Multidisciplinary

Enantioselective, intermolecular benzylic C-H amination catalysed by an engineered iron-haem enzyme

Christopher K. Prier et al.

NATURE CHEMISTRY (2017)

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Article Chemistry, Multidisciplinary

Co/NHPI-mediated aerobic oxygenation of benzylic C-H bonds in pharmaceutically relevant molecules

Damian P. Hruszkewycz et al.

CHEMICAL SCIENCE (2017)

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Article Chemistry, Organic

Benzylic C(sp3)-H Functionalization for C-N and C-O Bond Formation via Visible Light Photoredox Catalysis

Ganesh Pandey et al.

JOURNAL OF ORGANIC CHEMISTRY (2016)

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Article Multidisciplinary Sciences

Scalable and sustainable electrochemical allylic C-H oxidation

Evan J. Horn et al.

NATURE (2016)

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Review Chemistry, Physical

Specific oxyfunctionalisations catalysed by peroxygenases: opportunities, challenges and solutions

Sebastian Bormann et al.

CATALYSIS SCIENCE & TECHNOLOGY (2015)

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Article Chemistry, Multidisciplinary

Horseradish peroxidase (HRP) as a tool in green chemistry

Guido R. Lopes et al.

RSC ADVANCES (2014)

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Article Chemistry, Applied

Visible-Light-Induced Metal-Free Allylic Oxidation Utilizing a Coupled Photocatalytic System of g-C3N4 and N-Hydroxy Compounds

Pengfei Zhang et al.

ADVANCED SYNTHESIS & CATALYSIS (2011)

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Article Chemistry, Physical

Mechanism of Laccase-TEMPO-Catalyzed Oxidation of Benzyl Alcohol

Sander A. Tromp et al.

CHEMCATCHEM (2010)

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Article Chemistry, Physical

Correlation between bond dissociation energies and spin distribution for the radicals of ethers: A DFT study

Katarzyna R. Przybylak et al.

JOURNAL OF MOLECULAR STRUCTURE-THEOCHEM (2010)

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Article Multidisciplinary Sciences

Biocatalytic Asymmetric Synthesis of Chiral Amines from Ketones Applied to Sitagliptin Manufacture

Christopher K. Savile et al.

SCIENCE (2010)

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Article Chemistry, Multidisciplinary

Catalysts on Demand: Selective Oxidations by Laboratory-Evolved Cytochrome P450 BM3

Jared C. Lewis et al.

CHIMIA (2009)

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Article Chemistry, Organic

Experimental and theoretical studies of the redox potentials of cyclic nitroxides

James P. Blinco et al.

JOURNAL OF ORGANIC CHEMISTRY (2008)

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Article Chemistry, Multidisciplinary

Cu-facilitated C-O bond formation using N-hydroxyphthalimide:: Efficient and selective functionalization of benzyl and allylic C-H bonds

Ji Min Lee et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2008)

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Review Biotechnology & Applied Microbiology

Laccase-mediator systems and their applications: A review

O. V. Morozova et al.

APPLIED BIOCHEMISTRY AND MICROBIOLOGY (2007)

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Review Chemistry, Multidisciplinary

Free radical functionalization of organic compounds catalyzed by N-hydroxyphthalimide

Francesco Recupero et al.

CHEMICAL REVIEWS (2007)

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Article Forestry

Degradation of a nonphenolic β-O-4 lignin model dimer by horseradish peroxidase with 1-hydroxybenzotriazole

Shingo Kawai et al.

JOURNAL OF WOOD SCIENCE (2006)

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Article Chemistry, Physical

Catalytic oxidations mediated by metal ions and nitroxyl radicals

Roger A. Sheldon et al.

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL (2006)

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Article Chemistry, Multidisciplinary

New mediators for the enzyme laccase: mechanistic features and selectivity in the oxidation of non-phenolic substrates

P Astolfi et al.

NEW JOURNAL OF CHEMISTRY (2005)

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Article Polymer Science

Oxidative degradation of cis- and trans-1,4-polybutadienes by horseradish peroxidase/1-hydroxybenzotriazole

M Enoki et al.

POLYMER DEGRADATION AND STABILITY (2004)

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Article Chemistry, Multidisciplinary

Oxidation of non-phenolic substrates with the laccase/N-hydroxyacetanilide system: Structure of the key intermediate from the mediator and mechanistic insight

G Cantarella et al.

NEW JOURNAL OF CHEMISTRY (2004)

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Article Chemistry, Organic

Mechanisms of the aerobic oxidation of alcohols to aldehydes and ketones, catalysed under mild conditions by persistent and non-persistent nitroxyl radicals and transition metal salts - Polar, enthalpic, and captodative effects

F Minisci et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2004)

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Article Chemistry, Applied

Valuable oxygenates by aerobic oxidation of polymers using metal/bromide homogeneous catalysts

W Partenheimer

CATALYSIS TODAY (2003)

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Article Biochemistry & Molecular Biology

Free radical versus electron-transfer routes of oxidation of hydrocarbons by laccase/mediator systems catalytic or stoichiometric procedures

G Cantarella et al.

JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC (2003)

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Article Biochemistry & Molecular Biology

Oxidative degradation of cis- and trans-1,4-polyisoprenes and vulcanized natural rubber with enzyme-mediator systems

M Enoki et al.

BIOMACROMOLECULES (2003)

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Article Chemistry, Multidisciplinary

A study of the oxidation of ethers with the enzyme laccase under mediation by two N-OH-type compounds

F d'Acunzo et al.

NEW JOURNAL OF CHEMISTRY (2003)

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Article Biochemistry & Molecular Biology

Comparing the catalytic efficiency of some mediators of laccase

M Fabbrini et al.

JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC (2002)

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Article Chemistry, Multidisciplinary

The radical rate-determining step in the oxidation of benzyl alcohols by two N-OH-type mediators of laccase: the polar N-oxyl radical intermediate

F d'Acunzo et al.

NEW JOURNAL OF CHEMISTRY (2002)

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Review Chemistry, Multidisciplinary

Oxidative mechanisms involved in lignin degradation by white-rot fungi

R ten Have et al.

CHEMICAL REVIEWS (2001)

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Article Chemistry, Organic

Catalytic oxyalkylation of alkenes with alkanes and molecular oxygen via a radical process using N-hydroxyphthalimide

T Hara et al.

JOURNAL OF ORGANIC CHEMISTRY (2001)

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Article Biochemistry & Molecular Biology

Enzymatic and electrochemical oxidation of N-hydroxy compounds -: Redox potential, electron-transfer kinetics, and radical stability

F Xu et al.

EUROPEAN JOURNAL OF BIOCHEMISTRY (2001)

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A Horseradish Peroxidase-Mediator System for Benzylic C-H Activation

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