Recent Advances and Perspectives on Expanding the Chemical Diversity of Lasso Peptides

Setmelanotide: First Approval

(2021) Anthony Markham   DRUGS

2020 FDA TIDES (Peptides and Oligonucleotides) Harvest

(2021) Othman Al Musaimi et al.   Pharmaceuticals

Light‐Controlled Tyrosine Nitration of Proteins

(2021) Tengfang Long et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Cell-Free Biosynthesis to Evaluate Lasso Peptide Formation and Enzyme–Substrate Tolerance

(2021) Yuanyuan Si et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Somatostatin Analogs in Clinical Practice: a Review

(2020) Mariana Gomes-Porras et al.   INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES

CanE, an Iron/2-Oxoglutarate-Dependent Lasso Peptide Hydroxylase from Streptomyces canus

(2020) Chen Zhang et al.   ACS Chemical Biology

Natural Products as Sources of New Drugs over the Nearly Four Decades from 01/1981 to 09/2019

(2020) David J. Newman et al.   JOURNAL OF NATURAL PRODUCTS

Identification, Cloning and Heterologous Expression of the Gene Cluster Directing RES-701-3, -4 Lasso Peptides Biosynthesis from a Marine Streptomyces Strain

(2020) Daniel Oves-Costales et al.   Marine Drugs

Lasso Peptides: Heterologous Production and Potential Medical Application

(2020) Cheng Cheng et al.   Frontiers in Bioengineering and Biotechnology

Reactivity-Based Screening for Citrulline-Containing Natural Products Reveals a Family of Bacterial Peptidyl Arginine Deiminases

(2020) Lonnie A. Harris et al.   ACS Chemical Biology

Investigations into PoyH, a promiscuous protease from polytheonamide biosynthesis

(2019) Maximilian J. Helf et al.   JOURNAL OF INDUSTRIAL MICROBIOLOGY & BIOTECHNOLOGY

Structural mechanism of transcription inhibition by lasso peptides microcin J25 and capistruin

(2019) Nathaniel R. Braffman et al.   PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA

Discovery and characterization of a novel C-terminal peptide carboxyl methyltransferase in a lassomycin-like lasso peptide biosynthetic pathway

(2019) Yu Su et al.   APPLIED MICROBIOLOGY AND BIOTECHNOLOGY

Assessing the Flexibility of the Prochlorosin 2.8 Scaffold for Bioengineering Applications

(2019) Julian D. Hegemann et al.   ACS Synthetic Biology

Structural Basis of Leader Peptide Recognition in Lasso Peptide Biosynthesis Pathway

(2019) Tomomi Sumida et al.   ACS Chemical Biology

Factors Governing the Thermal Stability of Lasso Peptides

(2019) Julian D. Hegemann   CHEMBIOCHEM

Pandonodin: A Proteobacterial Lasso Peptide with an Exceptionally Long C-Terminal Tail

(2019) Wai Ling Cheung-Lee et al.   ACS Chemical Biology

Discovery of ubonodin, an antimicrobial lasso peptide active against members of the Burkholderia cepacia complex

(2019) Wai Ling Cheung-Lee et al.   CHEMBIOCHEM

Bremelanotide for the Treatment of Hypoactive Sexual Desire Disorder

(2019) Sheryl A. Kingsberg et al.   OBSTETRICS AND GYNECOLOGY

Steric complementarity directs sequence promiscuous leader binding in RiPP biosynthesis

(2019) Jonathan R. Chekan et al.   PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA

Incorporation of Nonproteinogenic Amino Acids in Class I and II Lantibiotics

(2018) Nidhi Kakkar et al.   ACS Chemical Biology

General rules of fragmentation evidencing lasso structures in CID and ETD

(2018) K. Jeanne Dit Fouque et al.   ANALYST

Biosynthetic Gene Cluster of a D-Tryptophan-Containing Lasso Peptide, MS-271

(2018) Zhi Feng et al.   CHEMBIOCHEM

Albusnodin: an acetylated lasso peptide from Streptomyces albus

(2018) Chuhan Zong et al.   CHEMICAL COMMUNICATIONS

Elucidation of the Roles of Conserved Residues in the Biosynthesis of the Lasso Peptide Paeninodin

(2018) Julian D Hegemann et al.   CHEMICAL COMMUNICATIONS

A lanthipeptide library used to identify a protein–protein interaction inhibitor

(2018) Xiao Yang et al.   Nature Chemical Biology

Development and Application of Yeast and Phage Display of Diverse Lanthipeptides

(2018) Kenton J. Hetrick et al.   ACS Central Science

Protecting Encapsulin Nanoparticles with Cysteine-Knot Miniproteins

(2018) Robin Klem et al.   MOLECULAR PHARMACEUTICS

Isolation and structure determination of a new lasso peptide specialicin based on genome mining

(2018) Issara Kaweewan et al.   BIOORGANIC & MEDICINAL CHEMISTRY

Enzymatic Reconstitution and Biosynthetic Investigation of the Lasso Peptide Fusilassin

(2018) Adam J. DiCaprio et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Heterologous and in Vitro Reconstitution of Fuscanodin, a Lasso Peptide from Thermobifida fusca

(2018) Joseph D. Koos et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

A genetics-free method for high-throughput discovery of cryptic microbial metabolites

(2018) Fei Xu et al.   Nature Chemical Biology

A new genome-mining tool redefines the lasso peptide biosynthetic landscape

(2017) Jonathan I Tietz et al.   Nature Chemical Biology

Phage display and selection of lanthipeptides on the carboxy-terminus of the gene-3 minor coat protein

(2017) Johannes H. Urban et al.   Nature Communications

Chimeric Leader Peptides for the Generation of Non-Natural Hybrid RiPP Products

(2017) Brandon J. Burkhart et al.   ACS Central Science

Leader Peptide-Free In Vitro Reconstitution of Microviridin Biosynthesis Enables Design of Synthetic Protease-Targeted Libraries

(2016) Emmanuel Reyna-González et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Structure and Mechanism of the Sphingopyxin I Lasso Peptide Isopeptidase

(2016) Christopher D. Fage et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Cyclisation mechanisms in the biosynthesis of ribosomally synthesised and post-translationally modified peptides

(2016) Andrew W Truman   Beilstein Journal of Organic Chemistry

Initial Molecular Recognition Steps of McjA Precursor during Microcin J25 Lasso Peptide Maturation

(2016) Nadine Assrir et al.   CHEMBIOCHEM

Dual substrate-controlled kinase activity leads to polyphosphorylated lasso peptides

(2016) Shaozhou Zhu et al.   FEBS LETTERS

Insights into the Unique Phosphorylation of the Lasso Peptide Paeninodin

(2016) Shaozhou Zhu et al.   JOURNAL OF BIOLOGICAL CHEMISTRY

Structure of the Lasso Peptide Isopeptidase Identifies a Topology for Processing Threaded Substrates

(2016) Jonathan R. Chekan et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Self-Assembly of Catenanes from Lasso Peptides

(2016) Caitlin D. Allen et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Seven enzymes create extraordinary molecular complexity in an uncultivated bacterium

(2016) Michael F. Freeman et al.   Nature Chemistry

Total chemical synthesis of lassomycin and lassomycin-amide

(2016) S. Lear et al.   ORGANIC & BIOMOLECULAR CHEMISTRY

Recombinant thiopeptides containing noncanonical amino acids

(2016) Xiaozhou Luo et al.   PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA

Structure-Activity Analysis of Gram-positive Bacterium-producing Lasso Peptides with Anti-mycobacterial Activity

(2016) Junji Inokoshi et al.   Scientific Reports

Lasso Peptide Biosynthetic Protein LarB1 Binds Both Leader and Core Peptide Regions of the Precursor Protein LarA

(2016) Wai Ling Cheung et al.   ACS Central Science

The B1 Protein Guides the Biosynthesis of a Lasso Peptide

(2016) Shaozhou Zhu et al.   Scientific Reports

Lasso Peptides: An Intriguing Class of Bacterial Natural Products

(2015) Julian D. Hegemann et al.   ACCOUNTS OF CHEMICAL RESEARCH

Construction of Lasso Peptide Fusion Proteins

(2015) Chuhan Zong et al.   ACS Chemical Biology

Characterization of Sviceucin from Streptomyces Provides Insight into Enzyme Exchangeability and Disulfide Bond Formation in Lasso Peptides

(2015) Yanyan Li et al.   ACS Chemical Biology

Interactions of a potent cyclic peptide inhibitor with the light chain of botulinum neurotoxin A: Insights from X-ray crystallography

(2015) Desigan Kumaran et al.   BIOORGANIC & MEDICINAL CHEMISTRY

Expanding the chemical diversity of lasso peptide MccJ25 with genetically encoded noncanonical amino acids

(2015) Frank J. Piscotta et al.   CHEMICAL COMMUNICATIONS

Structure, Bioactivity, and Resistance Mechanism of Streptomonomicin, an Unusual Lasso Peptide from an Understudied Halophilic Actinomycete

(2015) Mikhail Metelev et al.   CHEMISTRY & BIOLOGY

DNA-based hybrid catalysis

(2015) Ana Rioz-Martínez et al.   CURRENT OPINION IN CHEMICAL BIOLOGY

Chaxapeptin, a Lasso Peptide from Extremotolerant Streptomyces leeuwenhoekii Strain C58 from the Hyperarid Atacama Desert

(2015) Somayah S. Elsayed et al.   JOURNAL OF ORGANIC CHEMISTRY

A prevalent peptide-binding domain guides ribosomal natural product biosynthesis

(2015) Brandon J Burkhart et al.   Nature Chemical Biology

I-TASSER server: new development for protein structure and function predictions

(2015) Jianyi Yang et al.   NUCLEIC ACIDS RESEARCH

Structure and mechanism of a bacterial host-protein citrullinating virulence factor, Porphyromonas gingivalis peptidylarginine deiminase

(2015) Theodoros Goulas et al.   Scientific Reports

Ion Mobility–Mass Spectrometry of Lasso Peptides: Signature of a Rotaxane Topology

(2014) Kevin Jeanne Dit Fouque et al.   ANALYTICAL CHEMISTRY

RadicalS-Adenosyl Methionine Epimerases: Regioselective Introduction of DiverseD-Amino Acid Patterns into Peptide Natural Products

(2014) Brandon I. Morinaka et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Site-Directed and Global Incorporation of Orthogonal and Isostructural Noncanonical Amino Acids into the Ribosomal Lasso Peptide Capistruin

(2014) Rashed S. Al Toma et al.   CHEMBIOCHEM

Targeting Mycobacterial Proteolytic Complexes with Natural Products

(2014) Tanya Parish   CHEMISTRY & BIOLOGY

Lassomycin, a Ribosomally Synthesized Cyclic Peptide, Kills Mycobacterium tuberculosis by Targeting the ATP-Dependent Protease ClpC1P1P2

(2014) Ekaterina Gavrish et al.   CHEMISTRY & BIOLOGY

Rational Improvement of the Affinity and Selectivity of Integrin Binding of Grafted Lasso Peptides

(2014) Julian D. Hegemann et al.   JOURNAL OF MEDICINAL CHEMISTRY

Design of a Cyclotide Antagonist of Neuropilin-1 and -2 That Potently Inhibits Endothelial Cell Migration

(2013) Jennifer A. Getz et al.   ACS Chemical Biology

Lasso peptides from proteobacteria: Genome mining employing heterologous expression and mass spectrometry

(2013) Julian D. Hegemann et al.   BIOPOLYMERS

Expanded genetic code for the engineering of ribosomally synthetized and post-translationally modified peptide natural products (RiPPs)

(2013) Nediljko Budisa   CURRENT OPINION IN BIOTECHNOLOGY

Prospecting genomes for lasso peptides

(2013) Mikhail O. Maksimov et al.   JOURNAL OF INDUSTRIAL MICROBIOLOGY & BIOTECHNOLOGY

Discovery and Characterization of an Isopeptidase That Linearizes Lasso Peptides

(2013) Mikhail O. Maksimov et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Designing and Producing Modified, New-to-Nature Peptides with Antimicrobial Activity by Use of a Combination of Various Lantibiotic Modification Enzymes

(2013) Auke J. van Heel et al.   ACS Synthetic Biology

Determination of Peptide Topology through Time-Resolved Double-Resonance under Electron Capture Dissociation Conditions

(2012) Marie Pérot-Taillandier et al.   ANALYTICAL CHEMISTRY

Dissecting the Maturation Steps of the Lasso Peptide Microcin J25 in vitro

(2012) Kok-Phen Yan et al.   CHEMBIOCHEM

Caulosegnins I–III: A Highly Diverse Group of Lasso Peptides Derived from a Single Biosynthetic Gene Cluster

(2012) Julian D. Hegemann et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

The nonribosomal synthesis of diketopiperazines in tRNA-dependent cyclodipeptide synthase pathways

(2012) Pascal Belin et al.   NATURAL PRODUCT REPORTS

Lasso peptides: structure, function, biosynthesis, and engineering

(2012) Mikhail O. Maksimov et al.   NATURAL PRODUCT REPORTS

Ribosomally synthesized and post-translationally modified peptide natural products: overview and recommendations for a universal nomenclature

(2012) Paul G. Arnison et al.   NATURAL PRODUCT REPORTS

Metagenome Mining Reveals Polytheonamides as Posttranslationally Modified Ribosomal Peptides

(2012) M. F. Freeman et al.   SCIENCE

Protease-Resistant Peptide Ligands from a Knottin Scaffold Library

(2011) Jennifer A. Getz et al.   ACS Chemical Biology

Congeneric Lantibiotics from Ribosomal In Vivo Peptide Synthesis with Noncanonical Amino Acids

(2011) Florian Oldach et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Introducing Lasso Peptides as Molecular Scaffolds for Drug Design: Engineering of an Integrin Antagonist

(2011) Thomas A. Knappe et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Asymmetric Catalysis with Helical Polymers

(2011) Rik P. Megens et al.   CHEMISTRY-A EUROPEAN JOURNAL

Bioinspired Catalyst Design and Artificial Metalloenzymes

(2011) Peter J. Deuss et al.   CHEMISTRY-A EUROPEAN JOURNAL

Ribosomal Route to Small-Molecule Diversity

(2011) Ma. Diarey B. Tianero et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Sequence Diversity in the Lasso Peptide Framework: Discovery of Functional Microcin J25 Variants with Multiple Amino Acid Substitutions

(2011) Si Jia Pan et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Topoisomer Differentiation of Molecular Knots by FTICR MS: Lessons from Class II Lasso Peptides

(2011) Séverine Zirah et al.   JOURNAL OF THE AMERICAN SOCIETY FOR MASS SPECTROMETRY

DNA-based asymmetric catalysis

(2010) Arnold J. Boersma et al.   CHEMICAL SOCIETY REVIEWS

Insights into the Biosynthesis and Stability of the Lasso Peptide Capistruin

(2009) Thomas A. Knappe et al.   CHEMISTRY & BIOLOGY

In Vitro Mutasynthesis of Lantibiotic Analogues Containing Nonproteinogenic Amino Acids

(2009) Matthew R. Levengood et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Follow the leader: the use of leader peptides to guide natural product biosynthesis

(2009) Trent J Oman et al.   Nature Chemical Biology

Systematic Structure-Activity Analysis of Microcin J25

(2008) Olga Pavlova et al.   JOURNAL OF BIOLOGICAL CHEMISTRY

Engineered Cystine-Knot Peptides that Bind αvβ3 Integrin with Antibody-Like Affinities

(2008) Adam P. Silverman et al.   JOURNAL OF MOLECULAR BIOLOGY