4.7 Article

Recent developments in promiscuous enzymatic reactions for carbon-nitrogen bond formation

Related references

Note: Only part of the references are listed.
Review Chemistry, Multidisciplinary

Enzymatic Formation of Indolactam Scaffold by C-N Bond-Forming Cytochrome P450 Oxidases in Teleocidin Biosynthesis

Iori Morita et al.

Summary: Teleocidins are potent protein kinase C activators with a unique indole-fused nine-membered lactam structure synthesized through a multi-step biosynthetic process involving NRPS, cytochrome P450 oxidase, prenyltransferase, and C-methyltransferase. Recent research has focused on elucidating the molecular basis for the challenging P450-catalyzed intramolecular C-N bond formation, leading to the generation of indolactam scaffold, as well as the production of unnatural and novel molecular scaffolds through precursor-directed biosynthesis using promiscuous P450 enzymes.

CHEMISTRY-A EUROPEAN JOURNAL (2021)

Review Chemistry, Physical

Organocatalyzed C-N bond-forming Reactions for the Synthesis of Amines and Amides

Rahul Upadhyay et al.

Summary: The synthesis of organonitrogen compounds via C-N bond formation is a versatile route for drug discovery. Organocatalyzed synthesis provides a sustainable and eco-compatible alternative, avoiding metal contamination.

CHEMCATCHEM (2021)

Article Chemistry, Physical

O-/N-/S-Specificity in Glycosyltransferase Catalysis: From Mechanistic Understanding to Engineering

David Teze et al.

Summary: The study found that UGT1 from Polygonum tinctorium can catalyze N-, O-, or S-glycosylation with similar rates, and elucidated the molecular basis of N-, O-, and S-specificities using experimental mutagenesis and simulations. It also showed that the active site can be engineered to increase or favor one of the three glycosylation activities over another, leading to the design of more active and specific enzyme variants for glycoside production.

ACS CATALYSIS (2021)

Review Chemistry, Applied

Recent Advances in Catalytic Asymmetric Aza-Michael Addition Triggered Cascade Reactions

Yong-Xing Song et al.

Summary: The aza-Michael addition cascade reaction is an important synthetic method for constructing functionalized C-N bonds, widely used in the synthesis of chiral drugs, intermediates, and natural products. This review highlights recent developments in asymmetric synthesis, including various types of aza-Michael addition triggered cascade reactions, reaction mechanisms, and derivatization experiments.

ADVANCED SYNTHESIS & CATALYSIS (2021)

Article Biochemistry & Molecular Biology

Functional Characterization of a Novel Glycosyltransferase (UGT73CD1) from Iris tectorum Maxim. for the Substrate promiscuity

Jia Huang et al.

Summary: UGT73CD1, identified from Iris tectorum, is a novel glycosyltransferase with broad catalytic promiscuity towards various substrates. This study provides insights into efficient biosynthesis of structurally diverse flavonoid glycosides for drug discovery.

MOLECULAR BIOTECHNOLOGY (2021)

Article Chemistry, Physical

Enzymatic Kinetic Resolution of Bulky Spiro-Epoxyoxindoles via Halohydrin Dehalogenase-Catalyzed Enantio- and Regioselective Azidolysis

Fang-Rui Zhang et al.

Summary: An efficient enzymatic process has been developed for the synthesis of valuable compounds through catalytic kinetic resolution, demonstrating synthetic utility and scalability.

ACS CATALYSIS (2021)

Review Chemistry, Organic

Photochemical Strategies for Carbon-Heteroatom Bond Formation

Cristian Cavedon et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2020)

Article Chemistry, Applied

Biocatalytic Aza-Michael Addition of Aromatic Amines to Enone Using α-Amylase in Water

Sunil Dutt et al.

ADVANCED SYNTHESIS & CATALYSIS (2020)

Article Chemistry, Multidisciplinary

Exploiting a C-N bond Forming Cytochrome P450 Monooxygenase for C-S Bond Formation

Iori Morita et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Article Chemistry, Multidisciplinary

Mechanism-Guided Design and Discovery of Efficient Cytochrome P450-Derived C-H Amination Biocatalysts

Viktoria Steck et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

Article Chemistry, Multidisciplinary

Structure and Function of NzeB, a Versatile C-C and C-N Bond-Forming Diketopiperazine Dimerase

Vikram V. Shende et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

Review Biotechnology & Applied Microbiology

Microbial lipases and their industrial applications: a comprehensive review

Prem Chandra et al.

MICROBIAL CELL FACTORIES (2020)

Review Chemistry, Multidisciplinary

Two decades of recent advances of Ugi reactions: synthetic and pharmaceutical applications

Manar Ahmed Fouad et al.

RSC ADVANCES (2020)

Article Chemistry, Physical

Biocatalytic Promiscuity of Lipases in Carbon-Phosphorus Bond Formation

Dominik Koszelewski et al.

CHEMCATCHEM (2019)

Article Biotechnology & Applied Microbiology

Lipase-catalyzed aza-Michael addition of amines to acrylates in supercritical carbon dioxide

Jiaxin Zhang et al.

JOURNAL OF CHEMICAL TECHNOLOGY AND BIOTECHNOLOGY (2019)

Article Biochemistry & Molecular Biology

Molecular basis for the P450-catalyzed C-N bond formation in indolactam biosynthesis

Fei He et al.

NATURE CHEMICAL BIOLOGY (2019)

Article Chemistry, Multidisciplinary

Enantioselective Aminohydroxylation of Styrenyl Olefins Catalyzed by an Engineered Hemoprotein

Inha Cho et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Review Chemistry, Multidisciplinary

The importance of catalytic promiscuity for enzyme design and evolution

Reuben B. Leveson-Gower et al.

NATURE REVIEWS CHEMISTRY (2019)

Review Chemistry, Multidisciplinary

Advances in Selective Carbon-Heteroatom Coupling Reactions

Qingle Zeng et al.

CHEMICAL RECORD (2018)

Review Chemistry, Multidisciplinary

Promiscuity of Lipase-Catalyzed Reactions for Organic Synthesis: A Recent Update

Bharat P. Dwivedee et al.

CHEMISTRYSELECT (2018)

Article Chemistry, Multidisciplinary

Lipase-mediated epoxidation of alkenes in supercritical carbon dioxide

Jiaxin Zhang et al.

GREEN CHEMISTRY LETTERS AND REVIEWS (2018)

Review Chemistry, Multidisciplinary

Green chemistry and catalysis in Mannich reaction

Jakub Iwanejko et al.

CURRENT OPINION IN GREEN AND SUSTAINABLE CHEMISTRY (2018)

Article Multidisciplinary Sciences

Genetically programmed chiral organoborane synthesis

S. B. Jennifer Kan et al.

NATURE (2017)

Article Chemistry, Multidisciplinary

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

Christopher K. Prier et al.

NATURE CHEMISTRY (2017)

Article Chemistry, Organic

One-pot construction of spirooxindole backbone via biocatalytic domino reaction

Yi-Ru Liang et al.

TETRAHEDRON LETTERS (2017)

Article Multidisciplinary Sciences

Engineered P450 biocatalysts show improved activity and regio-promiscuity in aromatic nitration

Ran Zuo et al.

SCIENTIFIC REPORTS (2017)

Review Chemistry, Organic

Applications of Michael Addition Reaction in Organic Synthesis

Gangliang Huang et al.

CURRENT ORGANIC SYNTHESIS (2017)

Review Chemistry, Multidisciplinary

Enzymatic Carbon-Sulfur Bond Formation in Natural Product Biosynthesis

Kyle L. Dunbar et al.

CHEMICAL REVIEWS (2017)

Article Chemistry, Multidisciplinary

Asymmetric Enzymatic Synthesis of Allylic Amines: A Sigmatropic Rearrangement Strategy

Christopher K. Prier et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2016)

Article Multidisciplinary Sciences

Directed evolution of cytochrome c for carbon-silicon bond formation: Bringing silicon to life

S. B. Jennifer Kan et al.

SCIENCE (2016)

Article Chemistry, Organic

Exploring the aglycon promiscuity of a new glycosyltransferase from Pueraria lobata

Lili Sun et al.

TETRAHEDRON LETTERS (2016)

Review Biochemistry & Molecular Biology

Recent developments in enzyme promiscuity for carbon-carbon bond-forming reactions

Yufeng Miao et al.

CURRENT OPINION IN CHEMICAL BIOLOGY (2015)

Article Chemistry, Applied

One-Pot Synthesis of Spirooxazino Derivatives via EnzymeInitiated Multicomponent Reactions

Jun-Liang Wang et al.

ADVANCED SYNTHESIS & CATALYSIS (2014)

Review Chemistry, Multidisciplinary

C-N bond forming cross-coupling reactions: an overview

Jitender Bariwal et al.

CHEMICAL SOCIETY REVIEWS (2013)

Article Chemistry, Organic

Lipase-Catalyzed Aza-Michael Reaction on Acrylate Derivatives

Peter Steunenberg et al.

JOURNAL OF ORGANIC CHEMISTRY (2013)

Article Biochemistry & Molecular Biology

A novel enzyme-catalyzed synthesis of N-substituted pyrrole derivatives

Hui Zheng et al.

MOLECULAR DIVERSITY (2013)

Article Chemistry, Organic

Model Studies on the First Enzyme-Catalyzed Ugi Reaction

Szymon Klossowski et al.

ORGANIC LETTERS (2013)

Review Chemistry, Applied

Recent Developments in Asymmetric Organocatalytic Domino Reactions

Helene Pellissier

ADVANCED SYNTHESIS & CATALYSIS (2012)

Article Chemistry, Organic

Promiscuous Behavior of Rhizomucor miehei Lipase in the Synthesis of N-Substituted ß-Amino Esters

Leandro N. Monsalve et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2012)

Article Chemistry, Organic

Catalytic activity of halohydrin dehalogenases towards spiroepoxides

Maja Majeric Elenkov et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2012)

Article Multidisciplinary Sciences

Protease-catalysed Direct Asymmetric Mannich Reaction in Organic Solvent

Yang Xue et al.

SCIENTIFIC REPORTS (2012)

Article Biochemistry & Molecular Biology

New view of acylase promiscuity: An extended study on the acylase-catalyzed Markovnikov addition

Bo-Kai Liu et al.

JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC (2011)

Article Biochemistry & Molecular Biology

Enzyme-mediated domino synthesis of 2-alkylbenzimidazoles in solvent-free system: A green route to heterocyclic compound

Li Wang et al.

JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC (2010)

Article Biochemistry & Molecular Biology

Utilization of biocatalytic promiscuity for direct Mannich reaction

Ting He et al.

JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC (2010)

Article Chemistry, Organic

Michael additions of primary and secondary amines to acrylonitrile catalyzed by lipases

Rodrigo O. M. A. de Souza et al.

TETRAHEDRON LETTERS (2009)

Article Biotechnology & Applied Microbiology

Two lipase-catalyzed sequential synthesis of drug derivatives in organic media

Bokai Liu et al.

ENZYME AND MICROBIAL TECHNOLOGY (2008)

Review Multidisciplinary Sciences

Carbon-heteroatom bond formation catalysed by organometallic complexes

John F. Hartwig

NATURE (2008)

Article Biochemistry & Molecular Biology

Chemoselective enzymatic preparation of N-hydroxyalkylacrylamides, monomers for hydrophilic polymer matrices

EM Rustoy et al.

JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC (2006)

Article Biochemistry & Molecular Biology

Exploring the active-site of a rationally redesigned lipase for catalysis of Michael-type additions

P Carlqvist et al.

CHEMBIOCHEM (2005)

Article Chemistry, Multidisciplinary

Penicillin G acylase catalyzed Markovnikov addition of allopurinol to vinyl ester

WB Wu et al.

CHEMICAL COMMUNICATIONS (2005)

Article Chemistry, Multidisciplinary

Lipase catalysed Michael addition of secondary amines to acrylonitrile

O Torre et al.

CHEMICAL COMMUNICATIONS (2004)

Review Chemistry, Multidisciplinary

Catalytic promiscuity in biocatalysis: Using old enzymes to form new bonds and follow new pathways

UT Bornscheuer et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2004)