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Incorporation of Nonproteinogenic Amino Acids in Class I and II Lantibiotics

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Download Hi-Res ImageDownload to MS-PowerPointCite This:ACS Chem. Biol. 2018, 13, 4, 951-957
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    Incorporation of Nonproteinogenic Amino Acids in Class I and II Lantibiotics
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    • Nidhi Kakkar
      Nidhi Kakkar
      Howard Hughes Medical Institute and Roger Adams Laboratory, Department of Chemistry, University of Illinois at Urbana—Champaign, 600 South Mathews Avenue, Urbana, Illinois 61801, United States
      More by Nidhi Kakkar
    • Jessica G. Perez
      Jessica G. Perez
      Department of Chemical and Biological Engineering, Northwestern University, Evanston, Illinois 60208, United States
      More by Jessica G. Perez
    • Wenshe R. Liu
      Wenshe R. Liu
      Department of Chemistry, Texas A&M University, College Station, Texas 77843m United States
      More by Wenshe R. Liu
      Orcidhttp://orcid.org/0000-0002-7078-6534
    • Michael C. Jewett
      Michael C. Jewett
      Department of Chemical and Biological Engineering, Northwestern University, Evanston, Illinois 60208, United States
      More by Michael C. Jewett
    • Wilfred A. van der Donk*
      Wilfred A. van der Donk
      Howard Hughes Medical Institute and Roger Adams Laboratory, Department of Chemistry, University of Illinois at Urbana—Champaign, 600 South Mathews Avenue, Urbana, Illinois 61801, United States
      *E-mail: [email protected]
      More by Wilfred A. van der Donk
      Orcidhttp://orcid.org/0000-0002-5467-7071
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    ACS Chemical Biology

    Cite this: ACS Chem. Biol. 2018, 13, 4, 951–957
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    https://doi.org/10.1021/acschembio.7b01024
    Published February 13, 2018
    Copyright © 2018 American Chemical Society
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    Abstract

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    Lantibiotics are ribosomally synthesized and post-translationally modified peptide natural products that contain thioether cross-links formed by lanthionine and methyllanthionine residues. They exert potent antimicrobial activity against Gram-positive bacteria. We herein report production of analogues of two lantibiotics, lacticin 481 and nisin, that contain nonproteinogenic amino acids using two different strategies involving amber stop codon suppression technology. These methods complement recent alternative approaches to incorporate nonproteinogenic amino acids into lantibiotics.

    Copyright © 2018 American Chemical Society

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    Supporting Information

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acschembio.7b01024.

    • Description of all molecular biology procedures, protein purifications, and supporting figures (PDF)

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    Cited By

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    This article is cited by 26 publications.

    1. Wei Niu, Jiantao Guo. Cellular Site-Specific Incorporation of Noncanonical Amino Acids in Synthetic Biology. Chemical Reviews 2024, 124 (18) , 10577-10617. https://doi.org/10.1021/acs.chemrev.3c00938
    2. Chayanid Ongpipattanakul, Emily K. Desormeaux, Adam DiCaprio, Wilfred A. van der Donk, Douglas A. Mitchell, Satish K. Nair. Mechanism of Action of Ribosomally Synthesized and Post-Translationally Modified Peptides. Chemical Reviews 2022, 122 (18) , 14722-14814. https://doi.org/10.1021/acs.chemrev.2c00210
    3. Samuel Gowland, Michael C. Jewett. Mobile Translation Systems Generate Genomically Engineered Escherichia coli Cells with Improved Growth Phenotypes. ACS Synthetic Biology 2022, 11 (9) , 2969-2978. https://doi.org/10.1021/acssynbio.2c00099
    4. Tung Le, Kevin Jeanne Dit Fouque, Miguel Santos-Fernandez, Claudio D. Navo, Gonzalo Jiménez-Osés, Raymond Sarksian, Francisco Alberto Fernandez-Lima, Wilfred A. van der Donk. Substrate Sequence Controls Regioselectivity of Lanthionine Formation by ProcM. Journal of the American Chemical Society 2021, 143 (44) , 18733-18743. https://doi.org/10.1021/jacs.1c09370
    5. Imran R. Rahman, Jeella Z. Acedo, Xiaoran Roger Liu, Lingyang Zhu, Justine Arrington, Michael L. Gross, Wilfred A. van der Donk. Substrate Recognition by the Class II Lanthipeptide Synthetase HalM2. ACS Chemical Biology 2020, 15 (6) , 1473-1486. https://doi.org/10.1021/acschembio.0c00127
    6. Rachael Dickman, Serena A. Mitchell, Angelo M. Figueiredo, D. Flemming Hansen, Alethea B. Tabor. Molecular Recognition of Lipid II by Lantibiotics: Synthesis and Conformational Studies of Analogues of Nisin and Mutacin Rings A and B. The Journal of Organic Chemistry 2019, 84 (18) , 11493-11512. https://doi.org/10.1021/acs.joc.9b01253
    7. Mateusz Musiejuk, Paweł Kafarski. Engineering of Nisin as a Means for Improvement of Its Pharmacological Properties: A Review. Pharmaceuticals 2023, 16 (8) , 1058. https://doi.org/10.3390/ph16081058
    8. S.T. Anne Sahithi, Marttin Paulraj Gundupalli, Vinodhini Shanmugam, Malinee Sriariyanun. Lantibiotics production—optimization and scale-up research: cutting edge and challenges. 2023, 427-459. https://doi.org/10.1016/B978-0-323-99141-4.00020-5
    9. Yuhui Du, Li Li, Yue Zheng, Jiaheng Liu, Julia Gong, Zekai Qiu, Yanni Li, Jianjun Qiao, Yi-Xin Huo, . Incorporation of Non-Canonical Amino Acids into Antimicrobial Peptides: Advances, Challenges, and Perspectives. Applied and Environmental Microbiology 2022, 88 (23) https://doi.org/10.1128/aem.01617-22
    10. Riccardo Iacovelli, Nika Sokolova, Kristina Haslinger. Striving for sustainable biosynthesis: discovery, diversification, and production of antimicrobial drugs in Escherichia coli. Biochemical Society Transactions 2022, 50 (5) , 1315-1328. https://doi.org/10.1042/BST20220218
    11. Chad W. Johnston, Ahmed H. Badran. Natural and engineered precision antibiotics in the context of resistance. Current Opinion in Chemical Biology 2022, 69 , 102160. https://doi.org/10.1016/j.cbpa.2022.102160
    12. Yue Zheng, Yuhui Du, Zekai Qiu, Ziming Liu, Jianjun Qiao, Yanni Li, Qinggele Caiyin. Nisin Variants Generated by Protein Engineering and Their Properties. Bioengineering 2022, 9 (6) , 251. https://doi.org/10.3390/bioengineering9060251
    13. Jessica G. Perez, Erik D. Carlson, Oliver Weisser, Camila Kofman, Kosuke Seki, Benjamin J. Des Soye, Ashty S. Karim, Michael C. Jewett. Improving genomically recoded Escherichia coli to produce proteins containing non‐canonical amino acids. Biotechnology Journal 2022, 17 (4) https://doi.org/10.1002/biot.202100330
    14. Hongting Tang, Pan Zhang, Xiaozhou Luo. Recent Technologies for Genetic Code Expansion and their Implications on Synthetic Biology Applications. Journal of Molecular Biology 2022, 434 (8) , 167382. https://doi.org/10.1016/j.jmb.2021.167382
    15. Mengjiao Wang, Christopher D. Fage, Yile He, Jinhui Mi, Yang Yang, Fei Li, Xiaoping An, Huahao Fan, Lihua Song, Shaozhou Zhu, Yigang Tong. Recent Advances and Perspectives on Expanding the Chemical Diversity of Lasso Peptides. Frontiers in Bioengineering and Biotechnology 2021, 9 https://doi.org/10.3389/fbioe.2021.741364
    16. Haigang Song, Antony J. Burton, Sally L. Shirran, Jūratė Fahrig‐Kamarauskaitė, Hannelore Kaspar, Tom W. Muir, Markus Künzler, James H. Naismith. Engineering of a Peptide α‐N‐Methyltransferase to Methylate Non‐Proteinogenic Amino Acids. Angewandte Chemie 2021, 133 (26) , 14440-14444. https://doi.org/10.1002/ange.202100818
    17. Haigang Song, Antony J. Burton, Sally L. Shirran, Jūratė Fahrig‐Kamarauskaitė, Hannelore Kaspar, Tom W. Muir, Markus Künzler, James H. Naismith. Engineering of a Peptide α‐N‐Methyltransferase to Methylate Non‐Proteinogenic Amino Acids. Angewandte Chemie International Edition 2021, 60 (26) , 14319-14323. https://doi.org/10.1002/anie.202100818
    18. Fleur Ruijne, Oscar P. Kuipers. Combinatorial biosynthesis for the generation of new-to-nature peptide antimicrobials. Biochemical Society Transactions 2021, 49 (1) , 203-215. https://doi.org/10.1042/BST20200425
    19. Manuel Montalbán-López, Thomas A. Scott, Sangeetha Ramesh, Imran R. Rahman, Auke J. van Heel, Jakob H. Viel, Vahe Bandarian, Elke Dittmann, Olga Genilloud, Yuki Goto, María José Grande Burgos, Colin Hill, Seokhee Kim, Jesko Koehnke, John A. Latham, A. James Link, Beatriz Martínez, Satish K. Nair, Yvain Nicolet, Sylvie Rebuffat, Hans-Georg Sahl, Dipti Sareen, Eric W. Schmidt, Lutz Schmitt, Konstantin Severinov, Roderich D. Süssmuth, Andrew W. Truman, Huan Wang, Jing-Ke Weng, Gilles P. van Wezel, Qi Zhang, Jin Zhong, Jörn Piel, Douglas A. Mitchell, Oscar P. Kuipers, Wilfred A. van der Donk. New developments in RiPP discovery, enzymology and engineering. Natural Product Reports 2021, 38 (1) , 130-239. https://doi.org/10.1039/D0NP00027B
    20. Hamid Reza Karbalaei-Heidari, Nediljko Budisa. Combating Antimicrobial Resistance With New-To-Nature Lanthipeptides Created by Genetic Code Expansion. Frontiers in Microbiology 2020, 11 https://doi.org/10.3389/fmicb.2020.590522
    21. Eva Feldeková, Kateřina Solichová, Šárka Horáčková, Monika Kumherová, Jan Kyselka. The impact of l-lanthionine supplementation on the production of nisin by lactococci. European Food Research and Technology 2020, 246 (4) , 845-851. https://doi.org/10.1007/s00217-020-03449-4
    22. Linna An, Wilfred A. van der Donk. Recent Progress in Lanthipeptide Biosynthesis, Discovery, and Engineering. 2020, 119-165. https://doi.org/10.1016/B978-0-12-409547-2.14625-6
    23. Joongoo Lee, Do Soon Kim, Michael C. Jewett. Recent Advances in Engineering Ribosomes for Natural Product Biosynthesis. 2020, 377-397. https://doi.org/10.1016/B978-0-12-409547-2.14839-5
    24. Xing Jin, Oh-Jin Park, Seok Hoon Hong. Incorporation of non-standard amino acids into proteins: challenges, recent achievements, and emerging applications. Applied Microbiology and Biotechnology 2019, 103 (7) , 2947-2958. https://doi.org/10.1007/s00253-019-09690-6
    25. Bradley C Bundy, J Porter Hunt, Michael C Jewett, James R Swartz, David W Wood, Douglas D Frey, Govind Rao. Cell-free biomanufacturing. Current Opinion in Chemical Engineering 2018, 22 , 177-183. https://doi.org/10.1016/j.coche.2018.10.003
    26. Yuki Goto, Hiroaki Suga. Engineering of RiPP pathways for the production of artificial peptides bearing various non-proteinogenic structures. Current Opinion in Chemical Biology 2018, 46 , 82-90. https://doi.org/10.1016/j.cbpa.2018.06.014
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    ACS Chemical Biology

    Cite this: ACS Chem. Biol. 2018, 13, 4, 951–957
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acschembio.7b01024
    Published February 13, 2018
    Copyright © 2018 American Chemical Society
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