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A BBE-like Oxidase, AsmF, Dictates the Formation of Naphthalenic Hydroxyl Groups in Ansaseomycin Biosynthesis

  • Shuang He Liu
    Shuang He Liu
    State Key Laboratory of Pharmaceutical Biotechnology, Institute of Functional Biomolecules, Chemistry and Biomedicine Innovation Center, School of Life Sciences, Nanjing University, Nanjing 210023, China
  • Yuan Yuan Wei
    Yuan Yuan Wei
    State Key Laboratory of Pharmaceutical Biotechnology, Institute of Functional Biomolecules, Chemistry and Biomedicine Innovation Center, School of Life Sciences, Nanjing University, Nanjing 210023, China
  • Yin Nan Xing
    Yin Nan Xing
    State Key Laboratory of Pharmaceutical Biotechnology, Institute of Functional Biomolecules, Chemistry and Biomedicine Innovation Center, School of Life Sciences, Nanjing University, Nanjing 210023, China
    More by Yin Nan Xing
  • Yu Chen
    Yu Chen
    State Key Laboratory of Coordination Chemistry, Jiangsu Key Laboratory of Advanced Organic Materials, Chemistry and Biomedicine Innovation Center, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023, China
    More by Yu Chen
  • Wen Wang
    Wen Wang
    State Key Laboratory of Pharmaceutical Biotechnology, Institute of Functional Biomolecules, Chemistry and Biomedicine Innovation Center, School of Life Sciences, Nanjing University, Nanjing 210023, China
    More by Wen Wang
  • Kai Biao Wang
    Kai Biao Wang
    State Key Laboratory of Pharmaceutical Biotechnology, Institute of Functional Biomolecules, Chemistry and Biomedicine Innovation Center, School of Life Sciences, Nanjing University, Nanjing 210023, China
  • Yong Liang
    Yong Liang
    State Key Laboratory of Coordination Chemistry, Jiangsu Key Laboratory of Advanced Organic Materials, Chemistry and Biomedicine Innovation Center, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023, China
    More by Yong Liang
  • Rui Hua Jiao*
    Rui Hua Jiao
    State Key Laboratory of Pharmaceutical Biotechnology, Institute of Functional Biomolecules, Chemistry and Biomedicine Innovation Center, School of Life Sciences, Nanjing University, Nanjing 210023, China
    *Email: [email protected] (R.H.J.).
    More by Rui Hua Jiao
  • Bo Zhang*
    Bo Zhang
    State Key Laboratory of Pharmaceutical Biotechnology, Institute of Functional Biomolecules, Chemistry and Biomedicine Innovation Center, School of Life Sciences, Nanjing University, Nanjing 210023, China
    *Email: [email protected] (B.Z.).
    More by Bo Zhang
  • , and 
  • Hui Ming Ge*
    Hui Ming Ge
    State Key Laboratory of Pharmaceutical Biotechnology, Institute of Functional Biomolecules, Chemistry and Biomedicine Innovation Center, School of Life Sciences, Nanjing University, Nanjing 210023, China
    *Email: [email protected] (H.M.G.).
    More by Hui Ming Ge
Cite this: Org. Lett. 2021, 23, 9, 3724–3728
Publication Date (Web):April 20, 2021
https://doi.org/10.1021/acs.orglett.1c01101
Copyright © 2021 American Chemical Society

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    Abstract

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    Ansaseomycins are ansamycin-type natural products produced through expression of the asm gene cluster in a heterologous host. A rare berberine bridge enzyme (BBE) like oxidase, AsmF, is encoded in the asm gene cluster. Deletion of asmF led to the accumulation of a series of structurally diverse compounds, all of which lacked the 23-hydroxyl group in naphthalenic motif. Our work demonstrated that AsmF dictated the formation of the naphthalenic hydroxyl group in ansaseomycin biosynthesis.

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    Cited By

    This article is cited by 6 publications.

    1. Shiyuan Wang, Min Wang, Chengbao Duan, Yongpeng Yao, Jinwei Ren, Ling Liu, Yuanyuan Pan, Gang Liu. A Berberine Bridge Enzyme-like Oxidase Mediates the Cage-like Acresorbicillinol C Biosynthesis. Organic Letters 2024, 26 (3) , 642-646. https://doi.org/10.1021/acs.orglett.3c03966
    2. Zhi Kai Guo, Yong Chao Wang, Ying Zi Tan, Ailiman Abulaizi, Zi Jun Xiong, Shi Qing Zhang, Yang Yang, La Ying Yang, Jing Shi. Nagimycins A and B, Antibacterial Ansamycin-Related Macrolactams from Streptomyces sp. NA07423. Organic Letters 2023, 25 (22) , 4203-4207. https://doi.org/10.1021/acs.orglett.3c01539
    3. Jin-Mei Zhang, Xuan Liu, Qian Wei, Chuanteng Ma, Dehai Li, Yi Zou. Berberine bridge enzyme-like oxidase-catalysed double bond isomerization acts as the pathway switch in cytochalasin synthesis. Nature Communications 2022, 13 (1) https://doi.org/10.1038/s41467-021-27931-z
    4. Wenwen Yi, Asif Wares Newaz, Kuo Yong, Mingzhu Ma, Xiao-Yuan Lian, Zhizhen Zhang. New Hygrocins K–U and Streptophenylpropanamide A and Bioactive Compounds from the Marine-Associated Streptomyces sp. ZZ1956. Antibiotics 2022, 11 (11) , 1455. https://doi.org/10.3390/antibiotics11111455
    5. Natalia Skrzypczak, Piotr Przybylski. Modifications, biological origin and antibacterial activity of naphthalenoid ansamycins. Natural Product Reports 2022, 39 (9) , 1653-1677. https://doi.org/10.1039/D2NP00002D
    6. Ting‐Yan Han, Kai Zhang, Gong‐Li Tang, Qiang Zhou. Characterizing Post‐PKS Modifications of 16‐Demethyl ‐rifamycin Revealed Two Dehydrogenases Diverting the Aromatization Mode of Naphthalenic Ring in Ansamycin Biosynthesis. Chinese Journal of Chemistry 2022, 40 (13) , 1553-1558. https://doi.org/10.1002/cjoc.202200098

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