Beyond peptide bond formation: the versatile role of condensation domains in natural product biosynthesis

Sofie Dekimpe and Joleen Masschelein

Nat. Prod. Rep., 2021, 38, 1910
DOI: 10.1039/D0NP00098A

Unrivalled diversity: the many roles and reactions of bacterial cytochromes P450 in secondary metabolism

Anja Greule, Jeanette E. Stok, James J. De Voss and Max J. Cryle

Nat. Prod. Rep., 2018, 35, 757
DOI: 10.1039/C7NP00063D

Structure and noncanonical chemistry of nonribosomal peptide biosynthetic machinery

Heather L. Condurso and Steven D. Bruner

Nat. Prod. Rep., 2012, 29, 1099
DOI: 10.1039/c2np20023f

Functional characterization of tlmH in Streptoalloteichus hindustanus E465-94 ATCC 31158 unveiling new insight into tallysomycinbiosynthesis and affording a novel bleomycin analog

Meifeng Tao, Liyan Wang, Evelyn Wendt-Pienkowski, Ningning Zhang, Dong Yang, Ute Galm, Jane M. Coughlin, Zhinan Xu and Ben Shen

Mol. BioSyst., 2010, 6, 349
DOI: 10.1039/B918106G

Type II non-ribosomal peptide synthetase proteins: structure, mechanism, and protein–protein interactions

Matt J. Jaremko, Tony D. Davis, Joshua C. Corpuz and Michael D. Burkart

Nat. Prod. Rep., 2020, 37, 355
DOI: 10.1039/C9NP00047J

Recent advances in HemN-like radical S-adenosyl-l-methionine enzyme-catalyzed reactions

Wen-Bing Jin, Sheng Wu, Yi-Fan Xu, Hua Yuan and Gong-Li Tang

Nat. Prod. Rep., 2020, 37, 17
DOI: 10.1039/C9NP00032A

The genome-wide sequence specificity of DNA cleavage by bleomycin analogues in human cells

Vincent Murray, Jon K. Chen, Dong Yang and Ben Shen

Bioorganic & Medicinal Chemistry, 2018, 26, 4168
DOI: 10.1016/j.bmc.2018.07.006

Recent developments in the identification and biosynthesis of antitumor drugs derived from microorganisms

Qi Gao, Sizhe Deng and Tianyu Jiang

Engineering Microbiology, 2022, 2, 100047
DOI: 10.1016/j.engmic.2022.100047

Update 1 of: α,β-Diamino Acids: Biological Significance and Synthetic Approaches

Alma Viso, Roberto Fernández de la Pradilla, Mariola Tortosa, Ana García and Aida Flores

Chem. Rev., 2011, 111, PR1
DOI: 10.1021/cr100127y

BlmB and TlmB Provide Resistance to the Bleomycin Family of Antitumor Antibiotics by N-Acetylating Metal-Free Bleomycin, Tallysomycin, Phleomycin, and Zorbamycin

Jane M. Coughlin, Jeffrey D. Rudolf, Evelyn Wendt-Pienkowski, Liyan Wang, Claudia Unsin, Ute Galm, Dong Yang, Meifeng Tao and Ben Shen

Biochemistry, 2014, 53, 6901
DOI: 10.1021/bi501121e

Characterization of Yatakemycin Gene Cluster Revealing a Radical S-Adenosylmethionine Dependent Methyltransferase and Highlighting Spirocyclopropane Biosynthesis

Wei Huang, Hui Xu, Yan Li, Feng Zhang, Xin-Ya Chen, Qing-Li He, Yasuhiro Igarashi and Gong-Li Tang

J. Am. Chem. Soc., 2012, 134, 8831
DOI: 10.1021/ja211098r

Genomes to natural products PRediction Informatics for Secondary Metabolomes (PRISM)

Michael A. Skinnider, Chris A. Dejong, Philip N. Rees, Chad W. Johnston, Haoxin Li, Andrew L. H. Webster, Morgan A. Wyatt and Nathan A. Magarvey

Nucleic Acids Res, 2015, gkv1012
DOI: 10.1093/nar/gkv1012

Structural Characterization of OxyD, a Cytochrome P450 Involved in β-Hydroxytyrosine Formation in Vancomycin Biosynthesis

Max J. Cryle, Anton Meinhart and Ilme Schlichting

Journal of Biological Chemistry, 2010, 285, 24562
DOI: 10.1074/jbc.M110.131904

A Hybrid NRPS-PKS Gene Cluster Related to the Bleomycin Family of Antitumor Antibiotics in Alteromonas macleodii Strains

Carolina Megumi Mizuno, Nikole E. Kimes, Mario López-Pérez, Eva Ausó, Francisco Rodriguez-Valera, Rohit Ghai and Axel Cloeckaert

PLoS ONE, 2013, 8, e76021
DOI: 10.1371/journal.pone.0076021

Radical SAM-mediated methylation reactions

Danica Galonić Fujimori

Current Opinion in Chemical Biology, 2013, 17, 597
DOI: 10.1016/j.cbpa.2013.05.032

MbtH homology codes to identify gifted microbes for genome mining

Richard H Baltz

Journal of Industrial Microbiology and Biotechnology, 2014, 41, 357
DOI: 10.1007/s10295-013-1360-9

Manipulating Protein–Protein Interactions in Nonribosomal Peptide Synthetase Type II Peptidyl Carrier Proteins

Matt J. Jaremko, D. John Lee, Ashay Patel, Victoria Winslow, Stanley J. Opella, J. Andrew McCammon and Michael D. Burkart

Biochemistry, 2017, 56, 5269
DOI: 10.1021/acs.biochem.7b00884

Unprecedented Noncanonical Features of the Nonlinear Nonribosomal Peptide Synthetase Assembly Line for WS9326A Biosynthesis

Myoun‐Su Kim, Munhyung Bae, Ye‐Eun Jung, Jung Min Kim, Sunghoon Hwang, Myoung Chong Song, Yeon Hee Ban, Eun Seo Bae, Suckchang Hong, Sang Kook Lee, Sun‐Shin Cha, Dong‐Chan Oh and Yeo Joon Yoon

Angewandte Chemie, 2021, 133, 19919
DOI: 10.1002/ange.202103872

Functional Characterization of tlmK Unveiling Unstable Carbinolamide Intermediates in the Tallysomycin Biosynthetic Pathway

Liyan Wang, Meifeng Tao, Evelyn Wendt-Pienkoski, Ute Galm, Jane M. Coughlin and Ben Shen

Journal of Biological Chemistry, 2009, 284, 8256
DOI: 10.1074/jbc.M900640200

Zorbamycin has a different DNA sequence selectivity compared with bleomycin and analogues

Jon K. Chen, Dong Yang, Ben Shen, Brett A. Neilan and Vincent Murray

Bioorganic & Medicinal Chemistry, 2016, 24, 6094
DOI: 10.1016/j.bmc.2016.09.072

Comparative Analysis of the Biosynthetic Gene Clusters and Pathways for Three Structurally Related Antitumor Antibiotics: Bleomycin, Tallysomycin, and Zorbamycin

Ute Galm, Evelyn Wendt-Pienkowski, Liyan Wang, Sheng-Xiong Huang, Claudia Unsin, Meifeng Tao, Jane M. Coughlin and Ben Shen

J. Nat. Prod., 2011, 74, 526
DOI: 10.1021/np1008152

Radical-Mediated Enzymatic Methylation: A Tale of Two SAMS

Qi Zhang, Wilfred A. van der Donk and Wen Liu

Acc. Chem. Res., 2012, 45, 555
DOI: 10.1021/ar200202c

Comparison of Strategies to Overcome Drug Resistance: Learning from Various Kingdoms

Hiroshi Ogawara

Molecules, 2018, 23, 1476
DOI: 10.3390/molecules23061476

Stereoselective Lewis Base‐Catalyzed Asymmetric Hydrosilylation of α‐Acetamido‐β‐enamino Esters: Straightforward Approach for the Construction of α,β‐Diamino Acid Derivatives

Yan Jiang, Xing Chen, Xiao‐Yan Hu, Chang Shu, Yong‐Hong Zhang, Yong‐Sheng Zheng, Chun‐Xia Lian, Wei‐Cheng Yuan and Xiao‐Mei Zhang

Adv Synth Catal, 2013, 355, 1931
DOI: 10.1002/adsc.201300184

Cytochrome P450sky Interacts Directly with the Nonribosomal Peptide Synthetase to Generate Three Amino Acid Precursors in Skyllamycin Biosynthesis

Stefanie Uhlmann, Roderich D. Süssmuth and Max J. Cryle

ACS Chem. Biol., 2013, 8, 2586
DOI: 10.1021/cb400555e

Functional Diversity of HemN-like Proteins

Jinduo Cheng, Wan-Qiu Liu, Xiaoyu Zhu and Qi Zhang

ACS Bio Med Chem Au, 2022, 2, 109
DOI: 10.1021/acsbiomedchemau.1c00058

Aminoacyl chain translocation catalysed by a type II thioesterase domain in an unusual non-ribosomal peptide synthetase

Shan Wang, William D. G. Brittain, Qian Zhang, Zhou Lu, Ming Him Tong, Kewen Wu, Kwaku Kyeremeh, Matthew Jenner, Yi Yu, Steven L. Cobb and Hai Deng

Nat Commun, 2022, 13
DOI: 10.1038/s41467-021-27512-0

Insights into an Unusual Nonribosomal Peptide Synthetase Biosynthesis

Tina M. Binz, Sonia I. Maffioli, Margherita Sosio, Stefano Donadio and Rolf Müller

Journal of Biological Chemistry, 2010, 285, 32710
DOI: 10.1074/jbc.M110.146803

Structure and Function of a Dehydrating Condensation Domain in Nonribosomal Peptide Biosynthesis

Jon B. Patteson, Camille Marie Fortinez, Andrew T. Putz, Juan Rodriguez-Rivas, L. Henry Bryant, Kamal Adhikari, Martin Weigt, T. Martin Schmeing and Bo Li

J. Am. Chem. Soc., 2022, 144, 14057
DOI: 10.1021/jacs.1c13404

Conserved biosynthetic pathways for phosalacine, bialaphos and newly discovered phosphonic acid natural products

Joshua AV Blodgett, Jun Kai Zhang, Xiaomin Yu and William W Metcalf

J Antibiot, 2016, 69, 15
DOI: 10.1038/ja.2015.77

Sequence analysis and specificity of distinct types of menaquinone methyltransferases indicate the widespread potential of methylmenaquinone production in bacteria and archaea

Dennis Wilkens, Reinhard Meusinger, Sascha Hein and Jörg Simon

Environmental Microbiology, 2021, 23, 1407
DOI: 10.1111/1462-2920.15344

Unprecedented Noncanonical Features of the Nonlinear Nonribosomal Peptide Synthetase Assembly Line for WS9326A Biosynthesis

Myoun‐Su Kim, Munhyung Bae, Ye‐Eun Jung, Jung Min Kim, Sunghoon Hwang, Myoung Chong Song, Yeon Hee Ban, Eun Seo Bae, Suckchang Hong, Sang Kook Lee, Sun‐Shin Cha, Dong‐Chan Oh and Yeo Joon Yoon

Angew Chem Int Ed, 2021, 60, 19766
DOI: 10.1002/anie.202103872

N-Heterocyclic Carbene-Catalyzed [3 + 4] Annulation of Enals and Alkenyl Thiazolones: Enantioselective Synthesis of Thiazole-Fused ε-Lactones

Zhi-Qin Liang, Liang Yi, Kun-Quan Chen and Song Ye

J. Org. Chem., 2016, 81, 4841
DOI: 10.1021/acs.joc.6b00313

Phosphonate Biochemistry

Geoff P. Horsman and David L. Zechel

Chem. Rev., 2017, 117, 5704
DOI: 10.1021/acs.chemrev.6b00536

Comparison of Antibiotic Resistance Mechanisms in Antibiotic-Producing and Pathogenic Bacteria

Hiroshi Ogawara

Molecules, 2019, 24, 3430
DOI: 10.3390/molecules24193430

A Designer Bleomycin with Significantly Improved DNA Cleavage Activity

Sheng-Xiong Huang, Zhiyang Feng, Liyan Wang, Ute Galm, Evelyn Wendt-Pienkowski, Dong Yang, Meifeng Tao, Jane M Coughlin, Yanwen Duan and Ben Shen

J. Am. Chem. Soc., 2012, 134, 13501
DOI: 10.1021/ja3056535

Classification of the Adenylation and Acyl-Transferase Activity of NRPS and PKS Systems Using Ensembles of Substrate Specific Hidden Markov Models

Barzan I. Khayatt, Lex Overmars, Roland J. Siezen, Christof Francke and Patrick C. Y. Woo

PLoS ONE, 2013, 8, e62136
DOI: 10.1371/journal.pone.0062136

RadicalS-Adenosylmethionine Enzymes

Joan B. Broderick, Benjamin R. Duffus, Kaitlin S. Duschene and Eric M. Shepard

Chem. Rev., 2014, 114, 4229
DOI: 10.1021/cr4004709

The discovery and development of microbial bleomycin analogues

Jieqian Kong, Liwei Yi, Yi Xiong, Yong Huang, Dong Yang, Xiaohui Yan, Ben Shen, Yanwen Duan and Xiangcheng Zhu

Appl Microbiol Biotechnol, 2018, 102, 6791
DOI: 10.1007/s00253-018-9129-8

Structural characterization of CYP165D3, a cytochrome P450 involved in phenolic coupling in teicoplanin biosynthesis

Max J. Cryle, Jessica Staaden and Ilme Schlichting

Archives of Biochemistry and Biophysics, 2011, 507, 163
DOI: 10.1016/j.abb.2010.10.017

Crystal Structure of the Zorbamycin-Binding Protein ZbmA, the Primary Self-Resistance Element in Streptomyces flavoviridis ATCC21892

Jeffrey D. Rudolf, Lance Bigelow, Changsoo Chang, Marianne E. Cuff, Jeremy R. Lohman, Chin-Yuan Chang, Ming Ma, Dong Yang, Shonda Clancy, Gyorgy Babnigg, Andrzej Joachimiak, George N. Phillips and Ben Shen

Biochemistry, 2015, 54, 6842
DOI: 10.1021/acs.biochem.5b01008

Genome Mining of Streptomyces mobaraensis DSM40847 as a Bleomycin Producer Providing a Biotechnology Platform To Engineer Designer Bleomycin Analogues

Hindra, Dong Yang, Qihui Teng, Liao-Bin Dong, Ivana Crnovčić, Tingting Huang, Huiming Ge and Ben Shen

Org. Lett., 2017, 19, 1386
DOI: 10.1021/acs.orglett.7b00283

Isolation of manumycin-type derivatives and genome characterization of a marine Streptomyces sp. C1-2

Sakkarn Chanadech, Duangkamol Ruen-ngam, Chakapong Intaraudom, Pattama Pittayakhajonwut, Sumet Chongruchiroj, Jaturong Pratuangdejkul and Chitti Thawai

Research in Microbiology, 2021, 172, 103812
DOI: 10.1016/j.resmic.2021.103812

Evolution of High Cellulolytic Activity in Symbiotic Streptomyces through Selection of Expanded Gene Content and Coordinated Gene Expression

Adam J. Book, Gina R. Lewin, Bradon R. McDonald, Taichi E. Takasuka, Evelyn Wendt-Pienkowski, Drew T. Doering, Steven Suh, Kenneth F. Raffa, Brian G. Fox, Cameron R. Currie and David M Hillis

PLoS Biol, 2016, 14, e1002475
DOI: 10.1371/journal.pbio.1002475

Engineered production and evaluation of 6′-deoxy-tallysomycin H-1 revealing new insights into the structure–activity relationship of the anticancer drug bleomycin

Dong Yang, Hindra, Liao-Bin Dong, Ivana Crnovcic and Ben Shen

J Antibiot, 2018, 71, 97
DOI: 10.1038/ja.2017.93

Antibiotic Resistance Mechanisms in Bacteria: Relationships Between Resistance Determinants of Antibiotic Producers, Environmental Bacteria, and Clinical Pathogens

Elizabeth Peterson and Parjit Kaur

Front. Microbiol., 2018, 9
DOI: 10.3389/fmicb.2018.02928