Recent advances in biocatalysis of nitrogen-containing heterocycles

Construction of an Alternative NAD + De Novo Biosynthesis Pathway

(2021) Yong Ding et al.   Advanced Science

Development of a versatile and efficient C–N lyase platform for asymmetric hydroamination via computational enzyme redesign

(2021) Yinglu Cui et al.   Nature Catalysis

Powering Artificial Enzymatic Cascades with Electrical Energy

(2020) Ammar Al‐Shameri et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Pictet–Spenglerases in alkaloid biosynthesis: Future applications in biocatalysis

(2020) Rebecca Roddan et al.   CURRENT OPINION IN CHEMICAL BIOLOGY

Biocatalysis in drug discovery and development

(2020) Anna Fryszkowska et al.   CURRENT OPINION IN CHEMICAL BIOLOGY

Monoamine Oxidase (MAO-N) Biocatalyzed Synthesis of Indoles from Indolines Prepared via Photocatalytic Cyclization/Arylative Dearomatization

(2020) Fei Zhao et al.   ACS Catalysis

Characterization of imine reductases in reductive amination for the exploration of structure-activity relationships

(2020) Sarah L. Montgomery et al.   Science Advances

Biocatalytic Access to 1,4-Diazepanes via Imine Reductase-Catalyzed Intramolecular Asymmetric Reductive Amination

(2020) Zefei Xu et al.   ACS Catalysis

Bioretrosynthesis of Functionalized N ‐Heterocycles from Glucose via One‐Pot Tandem Collaborations of Designed Microbes

(2020) Jing Feng et al.   Advanced Science

Hemoglobin: a new biocatalyst for the synthesis of 2-substituted benzoxazoles via oxidative cyclization

(2019) Fengxi Li et al.   ChemCatChem

Refining and expanding nonribosomal peptide synthetase function and mechanism

(2019) Matt McErlean et al.   JOURNAL OF INDUSTRIAL MICROBIOLOGY & BIOTECHNOLOGY

Design and use of de novo cascades for new benzylisoquinoline alkaloid biosynthesis

(2019) Helen Claire Hailes et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Cascade Biotransformation to Access 3‐Methylpiperidine in Whole Cells

(2019) Niels Borlinghaus et al.   ChemCatChem

Enzymatic Pictet–Spengler Reaction: Computational Study of the Mechanism and Enantioselectivity of Norcoclaurine Synthase

(2019) Xiang Sheng et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Biocatalytic Asymmetric Synthesis of N-Aryl-Functionalized Amino Acids and Substituted Pyrazolidinones

(2019) Haigen Fu et al.   ACS Catalysis

Fungal indole alkaloid biogenesis through evolution of a bifunctional reductase/Diels–Alderase

(2019) Qingyun Dan et al.   Nature Chemistry

Acceptance and Kinetic Resolution of α-Methyl-Substituted Aldehydes by Norcoclaurine Synthases

(2019) Rebecca Roddan et al.   ACS Catalysis

Engineered enzymes that retain and regenerate their cofactors enable continuous-flow biocatalysis

(2019) Carol J. Hartley et al.   Nature Catalysis

One-Pot Biocatalytic Cascade Reduction of Cyclic Enimines for the Preparation of Diastereomerically Enriched N-Heterocycles

(2019) Thomas W. Thorpe et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Asymmetric Synthesis of Dihydropinidine Enabled by Concurrent Multienzyme Catalysis and a Biocatalytic Alternative to Krapcho Dealkoxycarbonylation

(2019) Natália Alvarenga et al.   ACS Catalysis

One-pot chemoenzymatic synthesis of trolline and tetrahydroisoquinoline analogues

(2018) Jianxiong Zhao et al.   CHEMICAL COMMUNICATIONS

Synthesis of chiral amines using redox biocatalysis

(2018) Gideon Grogan   CURRENT OPINION IN CHEMICAL BIOLOGY

An artificial synthetic pathway for acetoin, 2,3-butanediol, and 2-butanol production from ethanol using cell free multi-enzyme catalysis

(2018) Liaoyuan Zhang et al.   GREEN CHEMISTRY

Characterization of a new microbial Pictet-Spenglerase NscbB affording the β-carboline skeletons from Nocardiopsis synnemataformans DSM 44143

(2018) Qi Chen et al.   JOURNAL OF BIOTECHNOLOGY

Remote C–H Hydroxylation by an α-Ketoglutarate-Dependent Dioxygenase Enables Efficient Chemoenzymatic Synthesis of Manzacidin C and Proline Analogs

(2018) Christian R. Zwick et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Computational redesign of enzymes for regio- and enantioselective hydroamination

(2018) Ruifeng Li et al.   Nature Chemical Biology

Synergistic Chemo/Biocatalytic Synthesis of Alkaloidal Tetrahydroquinolines

(2018) Sebastian C. Cosgrove et al.   ACS Catalysis

Biocatalytic Access to Piperazines from Diamines and Dicarbonyls

(2018) Niels Borlinghaus et al.   ACS Catalysis

A Magnetic Heterogeneous Biocatalyst Composed of Immobilized Laccase and 2,2,6,6-Tetramethylpiperidine-1-oxyl (TEMPO) for Green One-Pot Cascade Synthesis of 2-Substituted Benzimidazole and Benzoxazole Derivatives under Mild Reaction Conditions

(2018) Mehdi Mogharabi-Manzari et al.   ADVANCED SYNTHESIS & CATALYSIS

Biocatalyzed C−C Bond Formation for the Production of Alkaloids

(2018) Mahesh D. Patil et al.   ChemCatChem

Synthesis of 2,5-Disubstituted Pyrrolidine Alkaloids via A One-Pot Cascade Using Transaminase and Reductive Aminase Biocatalysts

(2018) Bruna Z. Costa et al.   ChemCatChem

Monoamine Oxidase (MAO-N) Whole Cell Biocatalyzed Aromatization of 1,2,5,6-Tetrahydropyridines into Pyridines

(2018) Anita Toscani et al.   ACS Catalysis

Horse Liver Alcohol Dehydrogenase-Catalyzed Oxidative Lactamization of Amino Alcohols

(2018) Lei Huang et al.   ACS Catalysis

Chemo-Enzymatic Synthesis of Pyrazines and Pyrroles

(2018) Jin Xu et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Paal–Knorr synthesis of pyrroles: from conventional to green synthesis

(2018) Avula Balakrishna et al.   CATALYSIS REVIEWS-SCIENCE AND ENGINEERING

Chemoenzymatic Synthesis of Substituted Azepanes by Sequential Biocatalytic Reduction and Organolithium-Mediated Rearrangement

(2018) Wojciech Zawodny et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Benzylisoquinoline Alkaloids Biosynthesis in Sacred Lotus

(2018) Ivette Menéndez-Perdomo et al.   MOLECULES

MOF-derived cobalt nanoparticles catalyze a general synthesis of amines

(2017) Rajenahally V. Jagadeesh et al.   SCIENCE

Simultaneous engineering of an enzyme's entrance tunnel and active site: the case of monoamine oxidase MAO-N

(2017) Guangyue Li et al.   Chemical Science

Enzyme catalysed Pictet-Spengler formation of chiral 1,1’-disubstituted- and spiro-tetrahydroisoquinolines

(2017) Benjamin R. Lichman et al.   Nature Communications

Unveiling the Biocatalytic Aromatizing Activity of Monoamine Oxidases MAO-N and 6-HDNO: Development of Chemoenzymatic Cascades for the Synthesis of Pyrroles

(2017) Nicoló Scalacci et al.   ACS Catalysis

Enzyme Cascades in Whole Cells for the Synthesis of Chiral Cyclic Amines

(2017) Lorna J. Hepworth et al.   ACS Catalysis

Fischer indole synthesis applied to the total synthesis of natural products

(2017) Majid M. Heravi et al.   RSC Advances

Oxidation of pyrene using a hemoglobin-catalyzed biocatalytic reaction

(2017) Haein Keum et al.   Applied Biological Chemistry

Bacterial Alkaloids Prevent Amoebal Predation

(2016) Martin Klapper et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Biotransformation of β-keto nitriles to chiral (S)-β-amino acids using nitrilase and ω-transaminase

(2016) Sam Mathew et al.   BIOTECHNOLOGY LETTERS

Asymmetric Synthesis of Isoquinoline Alkaloids: 2004–2015

(2016) Maria Chrzanowska et al.   CHEMICAL REVIEWS

An NAD(P)H-Dependent Artificial Transfer Hydrogenase for Multienzymatic Cascades

(2016) Yasunori Okamoto et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Evaluation of Biosynthetic Pathway and Engineered Biosynthesis of Alkaloids

(2016) Shinji Kishimoto et al.   MOLECULES

Structures of two distinct conformations of holo-non-ribosomal peptide synthetases

(2016) Eric J. Drake et al.   NATURE

Structural basis of nonribosomal peptide macrocyclization in fungi

(2016) Jinru Zhang et al.   Nature Chemical Biology

Synthesis of Imidazolidin-4-ones via a Cytochrome P450-Catalyzed Intramolecular C–H Amination

(2016) Xinkun Ren et al.   ACS Catalysis

One-Pot Cascade Synthesis of Mono- and Disubstituted Piperidines and Pyrrolidines using Carboxylic Acid Reductase (CAR), ω-Transaminase (ω-TA), and Imine Reductase (IRED) Biocatalysts

(2016) Scott P. France et al.   ACS Catalysis

ATLAS of Biochemistry: A Repository of All Possible Biochemical Reactions for Synthetic Biology and Metabolic Engineering Studies

(2016) Noushin Hadadi et al.   ACS Synthetic Biology

A Novel Enzymatic Strategy for the Synthesis of Substituted Tetrahydroisoquinolines

(2016) Alessandra Bonamore et al.   ChemistrySelect

Mechanistic Analysis of an Engineered Enzyme that Catalyzes the Formose Reaction

(2015) Sean Poust et al.   CHEMBIOCHEM

Galactose Oxidase Variants for the Oxidation of Amino Alcohols in Enzyme Cascade Synthesis

(2015) Susanne Herter et al.   ChemCatChem

Structural Basis for β-Carboline Alkaloid Production by the Microbial Homodimeric Enzyme McbB

(2015) Takahiro Mori et al.   CHEMISTRY & BIOLOGY

Drug Oxidation by Cytochrome P450BM3: Metabolite Synthesis and Discovering New P450 Reaction Types

(2015) Xinkun Ren et al.   CHEMISTRY-A EUROPEAN JOURNAL

Using Strictosidine Synthase to Prepare Novel Alkaloids

(2015) Huajian Zhu et al.   CURRENT MEDICINAL CHEMISTRY

One-pot triangular chemoenzymatic cascades for the syntheses of chiral alkaloids from dopamine

(2015) B. R. Lichman et al.   GREEN CHEMISTRY

The development of an industrial-scale fed-batch fermentation simulation

(2015) Stephen Goldrick et al.   JOURNAL OF BIOTECHNOLOGY

De novo production of the key branch point benzylisoquinoline alkaloid reticuline in yeast

(2015) Isis J. Trenchard et al.   METABOLIC ENGINEERING

Computational protein design enables a novel one-carbon assimilation pathway

(2015) Justin B. Siegel et al.   PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA

Complete biosynthesis of opioids in yeast

(2015) S. Galanie et al.   SCIENCE

Stereoselective Cascade to C3-Methylated Strictosidine Derivatives Employing Transaminases and Strictosidine Synthases

(2015) Eva-Maria Fischereder et al.   ACS Catalysis

Enzymatic C(sp3)-H Amination: P450-Catalyzed Conversion of Carbonazidates into Oxazolidinones

(2015) Ritesh Singh et al.   ACS Catalysis

Classics in Chemical Neuroscience: Diazepam (Valium)

(2014) Nicholas E. Calcaterra et al.   ACS Chemical Neuroscience

Asymmetric synthesis of tetrahydroisoquinolines by enzymatic Pictet–Spengler reaction

(2014) Masakatsu Nishihachijo et al.   BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY

Catalytic bio–chemo and bio–bio tandem oxidation reactions for amide and carboxylic acid synthesis

(2014) Beatrice Bechi et al.   GREEN CHEMISTRY

Heterocycle construction using the biomass-derived building block itaconic acid

(2014) Alexandra M. Medway et al.   GREEN CHEMISTRY

Analysis of the Structural Diversity, Substitution Patterns, and Frequency of Nitrogen Heterocycles among U.S. FDA Approved Pharmaceuticals

(2014) Edon Vitaku et al.   JOURNAL OF MEDICINAL CHEMISTRY

Enzyme-Controlled Nitrogen-Atom Transfer Enables Regiodivergent C–H Amination

(2014) Todd K. Hyster et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Biosynthesis of fungal indole alkaloids

(2014) Wei Xu et al.   NATURAL PRODUCT REPORTS

The Evolutionary Fate of the Horizontally Transferred Agrobacterial Mikimopine Synthase Gene in the Genera Nicotiana and Linaria

(2014) Viera Kovacova et al.   PLoS One

Atlas of nonribosomal peptide and polyketide biosynthetic pathways reveals common occurrence of nonmodular enzymes

(2014) H. Wang et al.   PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA

Facile one-pot synthesis of tetrahydroisoquinolines from amino acids via hypochlorite-mediated decarboxylation and Pictet–Spengler condensation

(2014) Justin J. Maresh et al.   TETRAHEDRON LETTERS

P450-Catalyzed Intramolecular sp3 C–H Amination with Arylsulfonyl Azide Substrates

(2014) Ritesh Singh et al.   ACS Catalysis

Complexity Generation in Fungal Peptidyl Alkaloid Biosynthesis: A Two-Enzyme Pathway to the Hexacyclic MDR Export Pump Inhibitor Ardeemin

(2013) Stuart W. Haynes et al.   ACS Chemical Biology

Enantioselective Intramolecular CH Amination Catalyzed by Engineered Cytochrome P450 Enzymes In Vitro and In Vivo

(2013) John A. McIntosh et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Improvement of Reticuline Productivity from Dopamine by Using EngineeredEscherichia coli

(2013) Ju-Sung KIM et al.   BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY

An Iterative, Bimodular Nonribosomal Peptide Synthetase that Converts Anthranilate and Tryptophan into Tetracyclic Asperlicins

(2013) Xue Gao et al.   CHEMISTRY & BIOLOGY

Clicking 3′-Azidothymidine into Novel Potent Inhibitors of Human Immunodeficiency Virus

(2013) Venkata Ramana Sirivolu et al.   JOURNAL OF MEDICINAL CHEMISTRY

Engineering an Enantioselective Amine Oxidase for the Synthesis of Pharmaceutical Building Blocks and Alkaloid Natural Products

(2013) Diego Ghislieri et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Biocatalytic retrosynthesis

(2013) Nicholas J Turner et al.   Nature Chemical Biology

A Branched Biosynthetic Pathway Is Involved in Production of Roquefortine and Related Compounds in Penicillium chrysogenum

(2013) Hazrat Ali et al.   PLoS One

Monoamine Oxidase (MAO-N) Catalyzed Deracemization of Tetrahydro-β-carbolines: Substrate Dependent Switch in Enantioselectivity

(2013) Diego Ghislieri et al.   ACS Catalysis

Regio- and Stereoselective Monoamination of Diketones without Protecting Groups

(2012) Robert C. Simon et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Directed Evolution of the Enzyme Monoamine Oxidase (MAO-N): Highly Efficient Chemo-enzymatic Deracemisation of the Alkaloid (±)-Crispine A

(2012) Ian Rowles et al.   ChemCatChem

Progress in palladium-based catalytic systems for the sustainable synthesis of annulated heterocycles: a focus on indole backbones

(2012) Mélanie Platon et al.   CHEMICAL SOCIETY REVIEWS

Laccase-catalyzed oxidation of Hantzsch 1,4-dihydropyridines to pyridines and a new one pot synthesis of pyridines

(2012) Heba T. Abdel-Mohsen et al.   GREEN CHEMISTRY

Cyclization of fungal nonribosomal peptides by a terminal condensation-like domain

(2012) Xue Gao et al.   Nature Chemical Biology

Synthetic cascades are enabled by combining biocatalysts with artificial metalloenzymes

(2012) V. Köhler et al.   Nature Chemistry

Convergent Kilogram-Scale Synthesis of Dual Orexin Receptor Antagonist

(2012) Mélina Girardin et al.   ORGANIC PROCESS RESEARCH & DEVELOPMENT

Comparative analysis of the biosynthetic systems for fungal bicyclo[2.2.2]diazaoctane indole alkaloids: the (+)/(−)-notoamide, paraherquamide and malbrancheamide pathways

(2012) Shengying Li et al.   MedChemComm

ω-Transaminases for the Production of Optically Pure Amines and Unnatural Amino Acids

(2012) Sam Mathew et al.   ACS Catalysis

The Pictet-Spengler Reaction in Nature and in Organic Chemistry

(2011) Joachim Stöckigt et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Phosphate mediated biomimetic synthesis of tetrahydroisoquinoline alkaloids

(2011) Thomas Pesnot et al.   CHEMICAL COMMUNICATIONS

Scaffold Tailoring by a Newly Detected Pictet–Spenglerase Activity of Strictosidine Synthase: From the Common Tryptoline Skeleton to the Rare Piperazino-indole Framework

(2011) Fangrui Wu et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Rilpivirine versus efavirenz with tenofovir and emtricitabine in treatment-naive adults infected with HIV-1 (ECHO): a phase 3 randomised double-blind active-controlled trial

(2011) Jean-Michel Molina et al.   LANCET

Biocatalytic production of tetrahydroisoquinolines

(2011) Bettina M. Ruff et al.   TETRAHEDRON LETTERS

A bacterial platform for fermentative production of plant alkaloids

(2011) Akira Nakagawa et al.   Nature Communications

Engineering a Biometallic Whole Cell Catalyst for Enantioselective Deracemization Reactions

(2011) Joanne M. Foulkes et al.   ACS Catalysis

Anthranilate-Activating Modules from Fungal Nonribosomal Peptide Assembly Lines

(2010) Brian D. Ames et al.   BIOCHEMISTRY

A Facile Chemoenzymatic Approach: One-Step Syntheses of Monoterpenoid Indole Alkaloids

(2010) Hong-Bin Zou et al.   Chemistry-An Asian Journal

The impact of aromatic ring count on compound developability: further insights by examining carbo- and hetero-aromatic and -aliphatic ring types

(2010) Timothy J. Ritchie et al.   DRUG DISCOVERY TODAY

An enzymatic, stereoselective synthesis of (S)-norcoclaurine

(2010) Alessandra Bonamore et al.   GREEN CHEMISTRY

Crystal Structures of HIV-1 Reverse Transcriptase with Etravirine (TMC125) and Rilpivirine (TMC278): Implications for Drug Design

(2010) Eric B. Lansdon et al.   JOURNAL OF MEDICINAL CHEMISTRY

Genome-Based Characterization of Two Prenylation Steps in the Assembly of the Stephacidin and Notoamide Anticancer Agents in a Marine-DerivedAspergillussp.

(2010) Yousong Ding et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Norcoclaurine Synthase: Mechanism of an Enantioselective Pictet-Spengler Catalyzing Enzyme

(2010) Alessandra Bonamore et al.   MOLECULES

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

(2010) C. K. Savile et al.   SCIENCE

Bienzymatic synthesis of benzothia/(oxa)zoles in aqueous medium

(2010) Atul Kumar et al.   TETRAHEDRON LETTERS

Biocatalytic asymmetric formation of tetrahydro-β-carbolines

(2010) Peter Bernhardt et al.   TETRAHEDRON LETTERS

Conformational Dynamics in the Acyl-CoA Synthetases, Adenylation Domains of Non-ribosomal Peptide Synthetases, and Firefly Luciferase

(2009) Andrew M. Gulick   ACS Chemical Biology

Aza-Tryptamine Substrates in Monoterpene Indole Alkaloid Biosynthesis

(2009) Hyang-Yeol Lee et al.   CHEMISTRY & BIOLOGY

Prenylated indole derivatives from fungi: structure diversity, biological activities, biosynthesis and chemoenzymatic synthesis

(2009) Shu-Ming Li   NATURAL PRODUCT REPORTS

Acetylaszonalenin Biosynthesis inNeosartorya fischeri

(2008) Wen-Bing Yin et al.   JOURNAL OF BIOLOGICAL CHEMISTRY

Notoamides F−K, Prenylated Indole Alkaloids Isolated from a Marine-DerivedAspergillussp.

(2008) Sachiko Tsukamoto et al.   JOURNAL OF NATURAL PRODUCTS

Strictosidine Synthase:  Mechanism of a Pictet−Spengler Catalyzing Enzyme†

(2007) Justin J. Maresh et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY