Bacterial terpene biosynthesis: challenges and opportunities for pathway engineering

Complete biosynthesis of cannabinoids and their unnatural analogues in yeast

(2019) Xiaozhou Luo et al.   NATURE

antiSMASH 5.0: updates to the secondary metabolite genome mining pipeline

(2019) Kai Blin et al.   NUCLEIC ACIDS RESEARCH

Bacterial Diterpene Biosynthesis

(2019) Jeroen S. Dickschat   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Automated structure prediction of trans-acyltransferase polyketide synthase products

(2019) Eric J. N. Helfrich et al.   Nature Chemical Biology

Combinatorial biosynthesis and the basis for substrate promiscuity in class I diterpene synthases

(2019) Meirong Jia et al.   METABOLIC ENGINEERING

Two Diterpene Synthases for Spiroalbatene and Cembrene A from Allokutzneria albata

(2018) Jan Rinkel et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Two Bacterial Diterpene Synthases from Allokutzneria albata Produce Bonnadiene, Phomopsene, and Allokutznerene

(2018) Lukas Lauterbach et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Toward industrial production of isoprenoids in Escherichia coli : Lessons learned from CRISPR-Cas9 based optimization of a chromosomally integrated mevalonate pathway

(2018) Jorge Alonso-Gutierrez et al.   BIOTECHNOLOGY AND BIOENGINEERING

Linking cytochrome P450 enzymes from Mycobacterium tuberculosis to their cognate ferredoxin partners

(2018) Sandra Ortega Ugalde et al.   APPLIED MICROBIOLOGY AND BIOTECHNOLOGY

Sodorifen Biosynthesis in the Rhizobacterium Serratia plymuthica Involves Methylation and Cyclization of MEP-Derived Farnesyl Pyrophosphate by a SAM-Dependent C-Methyltransferase

(2018) Stephan von Reuss et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Generation of a cluster-free Streptomyces albus chassis strains for improved heterologous expression of secondary metabolite clusters

(2018) Maksym Myronovskyi et al.   METABOLIC ENGINEERING

Towards a comprehensive understanding of the structural dynamics of a bacterial diterpene synthase during catalysis

(2018) Ronja Driller et al.   Nature Communications

A Toolbox for Diverse Oxyfunctionalisation of Monoterpenes

(2018) Aitor Hernandez-Ortega et al.   Scientific Reports

Escherichia coli “Marionette” strains with 12 highly optimized small-molecule sensors

(2018) Adam J. Meyer et al.   Nature Chemical Biology

Uncoupled activation and cyclization in catmint reductive terpenoid biosynthesis

(2018) Benjamin R. Lichman et al.   Nature Chemical Biology

The antiSMASH database version 2: a comprehensive resource on secondary metabolite biosynthetic gene clusters

(2018) Kai Blin et al.   NUCLEIC ACIDS RESEARCH

Two-step pathway for isoprenoid synthesis

(2018) Alkiviadis Orfefs Chatzivasileiou et al.   PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA

Cytochromes P450 for natural product biosynthesis in Streptomyces: sequence, structure, and function

(2017) Jeffrey D. Rudolf et al.   NATURAL PRODUCT REPORTS

A synthetic biochemistry platform for cell free production of monoterpenes from glucose

(2017) Tyler P. Korman et al.   Nature Communications

Development of a Terpenoid-Production Platform in Streptomyces reveromyceticus SN-593

(2017) Ammara Khalid et al.   ACS Synthetic Biology

Artemisinin-A Gift from Traditional Chinese Medicine to the World (Nobel Lecture)

(2016) Youyou Tu   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Expanding the Landscape of Diterpene Structural Diversity through Stereochemically Controlled Combinatorial Biosynthesis

(2016) Johan Andersen-Ranberg et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Cellular Assays for Ferredoxins: A Strategy for Understanding Electron Flow through Protein Carriers That Link Metabolic Pathways

(2016) Joshua T. Atkinson et al.   BIOCHEMISTRY

Biosynthetic Origin of the Ether Ring in Platensimycin

(2016) Jeffrey D. Rudolf et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

The Cytochrome P450-Catalyzed Oxidative Rearrangement in the Final Step of Pentalenolactone Biosynthesis: Substrate Structure Determines Mechanism

(2016) Lian Duan et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Extreme promiscuity of a bacterial and a plant diterpene synthase enables combinatorial biosynthesis

(2016) Meirong Jia et al.   METABOLIC ENGINEERING

Combinatory optimization of chromosomal integrated mevalonate pathway for β-carotene production in Escherichia coli

(2016) Lijun Ye et al.   Microbial Cell Factories

Bacterial terpene cyclases

(2016) Jeroen S. Dickschat   NATURAL PRODUCT REPORTS

Elucidation of gibberellin biosynthesis in bacteria reveals convergent evolution

(2016) Ryan S Nett et al.   Nature Chemical Biology

A single terpene synthase is responsible for a wide variety of sesquiterpenes in Sorangium cellulosum Soce56

(2016) Alexander Schifrin et al.   ORGANIC & BIOMOLECULAR CHEMISTRY

Overcoming heterologous protein interdependency to optimize P450-mediated Taxol precursor synthesis inEscherichia coli

(2016) Bradley Walters Biggs et al.   PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA

Probing the promiscuity ofent-kaurene oxidases via combinatorial biosynthesis

(2016) Sibongile Mafu et al.   PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA

Bacterial Production of Pinene by a Laboratory-Evolved Pinene-Synthase

(2016) Miki Tashiro et al.   ACS Synthetic Biology

Redox Partner Interaction Sites in Cytochrome P450 Monooxygenases:In SilicoAnalysis and Experimental Validation

(2016) Łukasz Gricman et al.   ChemistrySelect

Structures and Biosynthesis of Corvol Ethers-Sesquiterpenes from the ActinomyceteKitasatospora setae

(2015) Patrick Rabe et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Conformational Analysis, Thermal Rearrangement, and EI-MS Fragmentation Mechanism of (1(10)E,4E,6S,7R)-Germacradien-6-ol by13C-Labeling Experiments

(2015) Patrick Rabe et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Principal component analysis of proteomics (PCAP) as a tool to direct metabolic engineering

(2015) Jorge Alonso-Gutierrez et al.   METABOLIC ENGINEERING

Metabolic and evolutionary origin of actin-binding polyketides from diverse organisms

(2015) Reiko Ueoka et al.   Nature Chemical Biology

Minimum Information about a Biosynthetic Gene cluster

(2015) Marnix H Medema et al.   Nature Chemical Biology

Discovery of microbial natural products by activation of silent biosynthetic gene clusters

(2015) Peter J. Rutledge et al.   NATURE REVIEWS MICROBIOLOGY

Bricks and blueprints: methods and standards for DNA assembly

(2015) Arturo Casini et al.   NATURE REVIEWS MOLECULAR CELL BIOLOGY

Induced-Fit Mechanism in Class I Terpene Cyclases

(2014) Philipp Baer et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Terpenoid Biosynthesis Off the Beaten Track: Unconventional Cyclases and Their Impact on Biomimetic Synthesis

(2014) Martin Baunach et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Acyl-Chain Elongation Drives Ketosynthase Substrate Selectivity intrans-Acyltransferase Polyketide Synthases

(2014) Matthew Jenner et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Enhancing Terpene Yield from Sugars via Novel Routes to 1-Deoxy-d-Xylulose 5-Phosphate

(2014) James Kirby et al.   APPLIED AND ENVIRONMENTAL MICROBIOLOGY

Reprogramming the Chemodiversity of Terpenoid Cyclization by Remolding the Active Site Contour of epi-Isozizaene Synthase

(2014) Ruiqiong Li et al.   BIOCHEMISTRY

In vitro reconstitution of mevalonate pathway and targeted engineering of farnesene overproduction inEscherichia coli

(2014) Fayin Zhu et al.   BIOTECHNOLOGY AND BIOENGINEERING

An Improved Technique for the Rapid Chemical Characterisation of Bacterial Terpene Cyclases

(2014) Jeroen S. Dickschat et al.   CHEMBIOCHEM

Cannabidiol: Pharmacology and potential therapeutic role in epilepsy and other neuropsychiatric disorders

(2014) Orrin Devinsky et al.   EPILEPSIA

A Methyltransferase Initiates Terpene Cyclization in Teleocidin B Biosynthesis

(2014) Takayoshi Awakawa et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Large-scale de novo DNA synthesis: technologies and applications

(2014) Sriram Kosuri et al.   NATURE METHODS

Terpene synthases are widely distributed in bacteria

(2014) Yuuki Yamada et al.   PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA

Biosynthesis of Ambiguine Indole Alkaloids in Cyanobacterium Fischerella ambigua

(2013) Matthew L. Hillwig et al.   ACS Chemical Biology

Identification and Characterization of Bacterial Diterpene Cyclases that Synthesize the Cembrane Skeleton

(2013) Ayuko Meguro et al.   CHEMBIOCHEM

Targeted Engineering of Cyclooctat-9-en-7-ol Synthase: A Stereospecific Access to Two New Non-natural Fusicoccane-Type Diterpenes

(2013) Christian Görner et al.   ChemCatChem

A Cytochrome P450 Serves as an Unexpected Terpene Cyclase during Fungal Meroterpenoid Biosynthesis

(2013) Yit-Heng Chooi et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Metabolic engineering of Escherichia coli for limonene and perillyl alcohol production

(2013) Jorge Alonso-Gutierrez et al.   METABOLIC ENGINEERING

Engineering dynamic pathway regulation using stress-response promoters

(2013) Robert H Dahl et al.   NATURE BIOTECHNOLOGY

Bacterial Synthesis of Diverse Indole Terpene Alkaloids by an Unparalleled Cyclization Sequence

(2012) Zhongli Xu et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Polyketide Proofreading by an Acyltransferase-like Enzyme

(2012) Katja Jensen et al.   CHEMISTRY & BIOLOGY

Bacterial diterpene synthases: new opportunities for mechanistic enzymology and engineered biosynthesis

(2012) Michael J Smanski et al.   CURRENT OPINION IN CHEMICAL BIOLOGY

Terpenoid synthase structures: a so far incomplete view of complex catalysis

(2012) Yang Gao et al.   NATURAL PRODUCT REPORTS

Production of amorphadiene in yeast, and its conversion to dihydroartemisinic acid, precursor to the antimalarial agent artemisinin

(2012) P. J. Westfall et al.   PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA

Evolution-guided engineering of nonribosomal peptide synthetase adenylation domains

(2012) Max Crüsemann et al.   Chemical Science

Cannabidiol enhances anandamide signaling and alleviates psychotic symptoms of schizophrenia

(2012) F M Leweke et al.   Translational Psychiatry

Cytochrome P450: taming a wild type enzyme

(2011) Sang Taek Jung et al.   CURRENT OPINION IN BIOTECHNOLOGY

Lessons and revelations from biomimetic syntheses

(2011) Mina Razzak et al.   Nature Chemical Biology

Scalable enantioselective total synthesis of taxanes

(2011) Abraham Mendoza et al.   Nature Chemistry

antiSMASH: rapid identification, annotation and analysis of secondary metabolite biosynthesis gene clusters in bacterial and fungal genome sequences

(2011) Marnix H. Medema et al.   NUCLEIC ACIDS RESEARCH

Enantioselective Synthesis of (−)-Englerins A and B

(2010) Kian Molawi et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Asymmetric, Protecting-Group-Free Total Synthesis of (−)-Englerin A

(2010) Qianghui Zhou et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Structure of Epi-Isozizaene Synthase fromStreptomyces coelicolorA3(2), a Platform for New Terpenoid Cyclization Templates,

(2010) Julie A. Aaron et al.   BIOCHEMISTRY

Streptomyces and Saccharopolyspora hosts for heterologous expression of secondary metabolite gene clusters

(2010) Richard H. Baltz   JOURNAL OF INDUSTRIAL MICROBIOLOGY & BIOTECHNOLOGY

Two rings in them all: The labdane-related diterpenoids

(2010) Reuben J. Peters   NATURAL PRODUCT REPORTS

Towards artificial terpene cyclases

(2010) Matthieu Willot et al.   Nature Chemistry

Combining metabolic and protein engineering of a terpenoid biosynthetic pathway for overproduction and selectivity control

(2010) E. Leonard et al.   PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA

Isoprenoid Pathway Optimization for Taxol Precursor Overproduction in Escherichia coli

(2010) P. K. Ajikumar et al.   SCIENCE

Two-Phase Terpene Total Synthesis: Historical Perspective and Application to the Taxol® Problem

(2010) Phil Baran et al.   SYNLETT

Characterization of a silent sesquiterpenoid biosynthetic pathway in Streptomyces avermitilis controlling epi-isozizaene albaflavenone biosynthesis and isolation of a new oxidized epi-isozizaene metabolite

(2010) Satoshi Takamatsu et al.   Microbial Biotechnology

Engineering Streptomyces coelicolor for heterologous expression of secondary metabolite gene clusters

(2010) Juan Pablo Gomez-Escribano et al.   Microbial Biotechnology

A Novel Semi-biosynthetic Route for Artemisinin Production Using Engineered Substrate-Promiscuous P450BM3

(2009) Jeffrey A. Dietrich et al.   ACS Chemical Biology

The Biosynthetic Logic of Polyketide Diversity

(2009) Christian Hertweck   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Engineered Streptomyces platensis Strains That Overproduce Antibiotics Platensimycin and Platencin

(2009) M. J. Smanski et al.   ANTIMICROBIAL AGENTS AND CHEMOTHERAPY

Rational Design of a Minimal and Highly Enriched CYP102A1 Mutant Library with Improved Regio-, Stereo- and Chemoselectivity

(2009) Alexander Seifert et al.   CHEMBIOCHEM

Adenylation Enzyme Characterization Using γ -18O4-ATP Pyrophosphate Exchange

(2009) Vanessa V. Phelan et al.   CHEMISTRY & BIOLOGY

Cloning and Heterologous Expression of the Cyclooctatin Biosynthetic Gene Cluster Afford a Diterpene Cyclase and Two P450 Hydroxylases

(2009) Seung-Young Kim et al.   CHEMISTRY & BIOLOGY

Biosynthesis of the Sesquiterpene Antibiotic Albaflavenone inStreptomyces coelicolor. Mechanism and Stereochemistry of the Enzymatic Formation of Epi-isozizaene

(2009) Xin Lin et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Synthetic lessons from nature

(2009) Huw M. L. Davies   NATURE

Total synthesis of eudesmane terpenes by site-selective C–H oxidations

(2009) Ke Chen et al.   NATURE

Enzymatic assembly of DNA molecules up to several hundred kilobases

(2009) Daniel G Gibson et al.   NATURE METHODS

Evolution of metabolic diversity: Insights from microbial polyketide synthases

(2009) Holger Jenke-Kodama et al.   PHYTOCHEMISTRY

Golden Gate Shuffling: A One-Pot DNA Shuffling Method Based on Type IIs Restriction Enzymes

(2009) Carola Engler et al.   PLoS One

Efficient synthesis of functional isoprenoids from acetoacetate through metabolic pathway-engineered Escherichia coli

(2008) Hisashi Harada et al.   APPLIED MICROBIOLOGY AND BIOTECHNOLOGY

Unearthing the roots of the terpenome

(2008) David W Christianson   CURRENT OPINION IN CHEMICAL BIOLOGY

Biochemistry and Molecular Genetics of the Biosynthesis of the Earthy Odorant Methylisoborneol inStreptomyces coelicolor

(2008) Chieh-Mei Wang et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Optimization of the mevalonate-based isoprenoid biosynthetic pathway in Escherichia coli for production of the anti-malarial drug precursor amorpha-4,11-diene

(2008) Jennifer R. Anthony et al.   METABOLIC ENGINEERING

Catalytic C–H functionalization by metal carbenoid and nitrenoid insertion

(2008) Huw M. L. Davies et al.   NATURE

Evolving biosynthetic tangos negotiate mechanistic landscapes

(2008) Michael B Austin et al.   Nature Chemical Biology

Geosmin Biosynthesis. Mechanism of the Fragmentation−Rearrangement in the Conversion of Germacradienol to Geosmin

(2007) Jiaoyang Jiang et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY