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Engineer P. multocida Heparosan Synthase 2 (PmHS2) for Size-Controlled Synthesis of Longer Heparosan Oligosaccharides
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    Engineer P. multocida Heparosan Synthase 2 (PmHS2) for Size-Controlled Synthesis of Longer Heparosan Oligosaccharides
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    • Lan Na
      Lan Na
      Department of Chemistry, University of California, One Shields Avenue, Davis, California 95616, United States
      More by Lan Na
    • Hai Yu*
      Hai Yu
      Department of Chemistry, University of California, One Shields Avenue, Davis, California 95616, United States
      *E-mail: [email protected] (H. Yu).
      More by Hai Yu
    • John B. McArthur
      John B. McArthur
      Department of Chemistry, University of California, One Shields Avenue, Davis, California 95616, United States
    • Tamashree Ghosh
      Tamashree Ghosh
      Department of Chemistry, University of California, One Shields Avenue, Davis, California 95616, United States
    • Thomas Asbell
      Thomas Asbell
      Department of Chemistry, University of California, One Shields Avenue, Davis, California 95616, United States
    • Xi Chen*
      Xi Chen
      Department of Chemistry, University of California, One Shields Avenue, Davis, California 95616, United States
      *E-mail: [email protected] (X. Chen).
      More by Xi Chen
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    ACS Catalysis

    Cite this: ACS Catal. 2020, 10, 11, 6113–6118
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    https://doi.org/10.1021/acscatal.0c01231
    Published May 11, 2020
    Copyright © 2020 American Chemical Society

    Abstract

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    Pasteurella multocida heparosan synthase 2 (PmHS2) is a dual-function polysaccharide synthase having both α1–4-N-acetylglucosaminyltransferase (α1–4-GlcNAcT) and β1–4-glucuronyltransferase (β1–4-GlcAT) activities located in two separate catalytic domains. We found that removing PmHS2 N-terminal 80-amino acid residues improved enzyme stability and expression level while retaining its substrate promiscuity. We also identified the reverse glycosylation activities of PmHS2, which complicated its application in size-controlled synthesis of oligosaccharides longer than hexasaccharide. Engineered Δ80PmHS2 single-function-glycosyltransferase mutants Δ80PmHS2_D291N (α1–4-GlcNAcT lacking both forward and reverse β1–4-GlcAT activities) and Δ80PmHS2_D569N (β1–4-GlcAT lacking both forward and reverse α1–4-GlcNAcT activities) were designed and showed to minimize side product formation. They were successfully used in a sequential one-pot multienzyme (OPME) platform for size-controlled high-yield production of oligosaccharides up to decasaccharide. The study draws attention to the consideration of reverse glycosylation activities of glycosyltransferases, including polysaccharide synthases, when applying them in the synthesis of oligosaccharides and polysaccharides. The mutagenesis strategy has the potential to be extended to other multifunctional polysaccharide synthases with reverse glycosylation activities to generate catalysts with improved synthetic efficiency.

    Copyright © 2020 American Chemical Society

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    Supporting Information

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    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acscatal.0c01231.

    • Supporting figures and experimental details for cloning and characterization of Δ80PmHS2 and mutants; detailed synthetic procedures, nuclear magnetic resonance (NMR) spectroscopy and high-resolution mass spectrometry (HRMS) data, and NMR spectra of products (PDF)

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    Cited By

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    This article is cited by 18 publications.

    1. Eduardo Stancanelli, Juno A. Krahn, Elizabeth Viverette, Robert Dutcher, Vijayakanth Pagadala, Mario J. Borgnia, Jian Liu, Lars C. Pedersen. Structural and Functional Analysis of Heparosan Synthase 2 from Pasteurella multocida to Improve the Synthesis of Heparin. ACS Catalysis 2024, 14 (9) , 6577-6588. https://doi.org/10.1021/acscatal.4c00677
    2. Jie Zheng, Han Xu, Bingzhi Li, Muhammad Sohail, Jingjing Bi, Fuming Zhang, Robert J. Linhardt, He Huang, Xing Zhang. Spatially Segregated MOF Bioreactor Enables Versatile Modular Glycoenzyme Assembly for Hierarchical Glycan Library Construction. ACS Applied Materials & Interfaces 2023, 15 (16) , 19807-19816. https://doi.org/10.1021/acsami.2c22094
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    6. Razia Sultana, Masamichi Kamihira. Bioengineered heparin: Advances in production technology. Biotechnology Advances 2024, 77 , 108456. https://doi.org/10.1016/j.biotechadv.2024.108456
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    8. Li-Li Sheng, Yi-Min Cai, Yi Li, Si-Ling Huang, Ju-Zheng Sheng. Advancements in heparosan production through metabolic engineering and improved fermentation. Carbohydrate Polymers 2024, 331 , 121881. https://doi.org/10.1016/j.carbpol.2024.121881
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    10. Maral Tsevelkhoroloo, Vijayalakshmi Dhakshnamoorthy, Young-Soo Hong, Chang-Ro Lee, Soon-Kwang Hong. Bifunctional and monofunctional α-neoagarooligosaccharide hydrolases from Streptomyces coelicolor A3(2). Applied Microbiology and Biotechnology 2023, 107 (12) , 3997-4008. https://doi.org/10.1007/s00253-023-12552-x
    11. Ha T. Le, Min Liu, Catherine L. Grimes. Application of bioanalytical and computational methods in decoding the roles of glycans in host-pathogen interactions. Current Opinion in Chemical Biology 2023, 74 , 102301. https://doi.org/10.1016/j.cbpa.2023.102301
    12. John Hogwood, Barbara Mulloy, Rebeca Lever, Elaine Gray, Clive P. Page. Pharmacology of Heparin and Related Drugs: An Update. Pharmacological Reviews 2023, 75 (2) , 328-379. https://doi.org/10.1124/pharmrev.122.000684
    13. Ganesh Nehru, Senthilkumar Sivaprakasam. Microbial Production of Heparosan. 2023, 1-16. https://doi.org/10.1007/978-3-030-81403-8_13-1
    14. Jian-Qun Deng, Zhen Lu, Juan Liu, Yan Zhao, Xu-Ben Hou, Xue-Ping Guo, Wen-Jie Jiang, Feng-Shan Wang, Ju-Zheng Sheng. Heparosan oligosaccharide synthesis using engineered single-function glycosyltransferases. Catalysis Science & Technology 2022, 12 (12) , 3793-3803. https://doi.org/10.1039/D1CY02061G
    15. Xiaoxiao Yang, Hai Yu, Xiaohong Yang, Anoopjit Singh Kooner, Yue Yuan, Bryant Luu, Xi Chen. One‐pot Multienzyme (OPME) Chemoenzymatic Synthesis of Brain Ganglioside Glycans with Human ST3GAL II Expressed in E. coli. ChemCatChem 2022, 14 (2) https://doi.org/10.1002/cctc.202101498
    16. Xiaohong Yang, Xiaoxiao Yang, Hai Yu, Lan Na, Tamashree Ghosh, John B. McArthur, Tsui-Fen Chou, Patricia Dickson, Xi Chen. A GH89 human α-N-acetylglucosaminidase (hNAGLU) homologue from gut microbe Bacteroides thetaiotaomicron capable of hydrolyzing heparosan oligosaccharides. AMB Express 2021, 11 (1) https://doi.org/10.1186/s13568-021-01253-1
    17. Han Xu, Baoxing Shen, Meng Qiao, Robert J. Linhardt, Xing Zhang. Recent advances on the one-pot synthesis to assemble size-controlled glycans and glycoconjugates and polysaccharides. Carbohydrate Polymers 2021, 258 , 117672. https://doi.org/10.1016/j.carbpol.2021.117672
    18. Lan Na, Riyao Li, Xi Chen. Recent progress in synthesis of carbohydrates with sugar nucleotide-dependent glycosyltransferases. Current Opinion in Chemical Biology 2021, 61 , 81-95. https://doi.org/10.1016/j.cbpa.2020.10.007

    ACS Catalysis

    Cite this: ACS Catal. 2020, 10, 11, 6113–6118
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acscatal.0c01231
    Published May 11, 2020
    Copyright © 2020 American Chemical Society

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