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Menaquinone Biosynthesis: Biochemical and Structural Studies of Chorismate Dehydratase

  • Nilkamal Mahanta
    Nilkamal Mahanta
    Department of Chemistry, Texas A&M University, College Station, Texas 77843, United States
  • Katherine A. Hicks
    Katherine A. Hicks
    Department of Chemistry, The State University of New York Cortland, Cortland, New York 13045, United States
  • Saad Naseem
    Saad Naseem
    Department of Chemistry, Texas A&M University, College Station, Texas 77843, United States
    More by Saad Naseem
  • Yang Zhang
    Yang Zhang
    Department of Chemistry and Chemical Biology, Cornell University, Ithaca, New York 14853, United States
    More by Yang Zhang
  • Dmytro Fedoseyenko
    Dmytro Fedoseyenko
    Department of Chemistry, Texas A&M University, College Station, Texas 77843, United States
  • Steven E. Ealick*
    Steven E. Ealick
    Department of Chemistry and Chemical Biology, Cornell University, Ithaca, New York 14853, United States
    *Department of Chemistry and Chemical Biology, Cornell University, Ithaca, NY 14853. E-mail: [email protected]
  • , and 
  • Tadhg P. Begley*
    Tadhg P. Begley
    Department of Chemistry, Texas A&M University, College Station, Texas 77843, United States
    *Department of Chemistry, Texas A&M University, College Station, TX 77843. E-mail: [email protected]
Cite this: Biochemistry 2019, 58, 14, 1837–1840
Publication Date (Web):March 11, 2019
https://doi.org/10.1021/acs.biochem.9b00105
Copyright © 2019 American Chemical Society

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    Abstract

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    Menaquinone (MK, vitamin K) is a lipid-soluble quinone that participates in the bacterial electron transport chain. In mammalian cells, vitamin K functions as an essential vitamin for the activation of several proteins involved in blood clotting and bone metabolism. MqnA is the first enzyme on the futalosine-dependent pathway to menaquinone and catalyzes the aromatization of chorismate by water loss. Here we report biochemical and structural studies of MqnA. These studies suggest that the dehydration reaction proceeds by a variant of the E1cb mechanism in which deprotonation is slower than water loss and that the enol carboxylate of the substrate is serving as the base.

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.biochem.9b00105.

    • Detailed procedures for overexpression and purification of MqnA, enzymatic assays, kinetics, H/D exchange, crystallization, and structure determination (PDF)

    Accession Codes

    UniProtKB/TrEMBL entry Q9RXE3, Protein Data Bank entry 6O9A.

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    Most electronic Supporting Information files are available without a subscription to ACS Web Editions. Such files may be downloaded by article for research use (if there is a public use license linked to the relevant article, that license may permit other uses). Permission may be obtained from ACS for other uses through requests via the RightsLink permission system: http://pubs.acs.org/page/copyright/permissions.html.

    Cited By

    This article is cited by 10 publications.

    1. Lihua Dong, Yongjun Liu. Exploring the Substrate-Assisted Dehydration of Chorismate Catalyzed by Dehydratase MqnA from QM/MM Calculations: The Role of Pocket Residues and the Hydrolysis Mechanism of N17D Mutant. Journal of Chemical Information and Modeling 2023, 63 (23) , 7499-7507. https://doi.org/10.1021/acs.jcim.3c01074
    2. Qihao Wu, Bailey A. Bell, Jia-Xuan Yan, Marc G. Chevrette, Nathan J. Brittin, Yanlong Zhu, Shaurya Chanana, Mitasree Maity, Doug R. Braun, Amelia M. Wheaton, Ilia A. Guzei, Ying Ge, Scott R. Rajski, Michael G. Thomas, Tim S. Bugni. Metabolomics and Genomics Enable the Discovery of a New Class of Nonribosomal Peptidic Metallophores from a Marine Micromonospora. Journal of the American Chemical Society 2023, 145 (1) , 58-69. https://doi.org/10.1021/jacs.2c06410
    3. PalfeyBruce A.Associate Professor, Biological Chemistry & Associate Director, Program in Chemical BiologySwitzerRebecca L.Assistant Professor of ChemistryRumin Zhang, VP, Head of Biochemistry, Volastra Therapeutics, Lauren Parr, PhD Candidate, Department of Chemistry, University of Iowa. Kinetics of Enzyme Catalysis. 2022https://doi.org/10.1021/acsinfocus.7e5015
    4. Hannah R. Manion-Sommerhalter, Dmytro Fedoseyenko, Sumedh Joshi, Tadhg P. Begley. Menaquinone Biosynthesis: The Mechanism of 5,8-Dihydroxy-2-naphthoate Synthase (MqnD). Biochemistry 2021, 60 (25) , 1947-1951. https://doi.org/10.1021/acs.biochem.1c00257
    5. Vikram V. Shende, Katherine D. Bauman, Bradley S. Moore. The shikimate pathway: gateway to metabolic diversity. Natural Product Reports 2024, 41 (4) , 604-648. https://doi.org/10.1039/D3NP00037K
    6. Feng Shi, Delbert Almerick T Boncan, Hin Ting Wan, Ting Fung Chan, Eric L. Zhang, Keng Po Lai, Chris Kong-Chu Wong. Hepatic metabolism gene expression and gut microbes in offspring, subjected to in-utero PFOS exposure and postnatal diet challenges. Chemosphere 2022, 308 , 136196. https://doi.org/10.1016/j.chemosphere.2022.136196
    7. Archna Prasad, Constanze Breithaupt, Duc-Anh Nguyen, Hauke Lilie, Jörg Ziegler, Milton T. Stubbs. Mechanism of chorismate dehydratase MqnA, the first enzyme of the futalosine pathway, proceeds via substrate-assisted catalysis. Journal of Biological Chemistry 2022, 298 (12) , 102601. https://doi.org/10.1016/j.jbc.2022.102601
    8. Panxing Sun, Feng Li, Yiwu Zong, Hao Song. Advances in the synthesis of menaquinone using microbial cell factories. Chinese Science Bulletin 2022, 67 (34) , 4055-4067. https://doi.org/10.1360/TB-2022-0532
    9. Zimeng Zhang, Linxia Liu, Chuan Liu, Yumei Sun, Dawei Zhang. New aspects of microbial vitamin K2 production by expanding the product spectrum. Microbial Cell Factories 2021, 20 (1) https://doi.org/10.1186/s12934-021-01574-7
    10. Florian Hubrich, Michael Müller, Jennifer N. Andexer. Chorismate- and isochorismate converting enzymes: versatile catalysts acting on an important metabolic node. Chemical Communications 2021, 57 (20) , 2441-2463. https://doi.org/10.1039/D0CC08078K

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