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Multiplexing of Combinatorial Chemistry in Antimycin Biosynthesis: Expansion of Molecular Diversity and Utility

Authors

  • Yan Yan,

    1. State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry (SIOC), Chinese Academy of Sciences (CAS), 345 Lingling Road, Shanghai 200032 (China)
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  • Dr. Jing Chen,

    1. State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry (SIOC), Chinese Academy of Sciences (CAS), 345 Lingling Road, Shanghai 200032 (China)
    2. Graduate School of Pharmaceutical Sciences, University of Tokyo, 7-3-1 Hongo, Bunkyo-ku (Japan)
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  • Lihan Zhang,

    1. Graduate School of Pharmaceutical Sciences, University of Tokyo, 7-3-1 Hongo, Bunkyo-ku (Japan)
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  • Qingfei Zheng,

    1. State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry (SIOC), Chinese Academy of Sciences (CAS), 345 Lingling Road, Shanghai 200032 (China)
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  • Ying Han,

    1. State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry (SIOC), Chinese Academy of Sciences (CAS), 345 Lingling Road, Shanghai 200032 (China)
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  • Hua Zhang,

    1. State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry (SIOC), Chinese Academy of Sciences (CAS), 345 Lingling Road, Shanghai 200032 (China)
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  • Daozhong Zhang,

    1. State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry (SIOC), Chinese Academy of Sciences (CAS), 345 Lingling Road, Shanghai 200032 (China)
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  • Prof. Dr. Takayoshi Awakawa,

    1. Graduate School of Pharmaceutical Sciences, University of Tokyo, 7-3-1 Hongo, Bunkyo-ku (Japan)
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  • Prof. Dr. Ikuro Abe,

    1. Graduate School of Pharmaceutical Sciences, University of Tokyo, 7-3-1 Hongo, Bunkyo-ku (Japan)
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  • Prof. Dr. Wen Liu

    Corresponding author
    1. State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry (SIOC), Chinese Academy of Sciences (CAS), 345 Lingling Road, Shanghai 200032 (China)
    • State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry (SIOC), Chinese Academy of Sciences (CAS), 345 Lingling Road, Shanghai 200032 (China)

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  • We thank Yu Cai at SIOC, CAS, and Prof. Junying Yuan at Harward Medical School for providing HeLa cells and assistance in cell-labeling experiments. This work was supported in part by grants from the NNSF (91213303), STCSM (13XD1404500), and “973 program” (2010CB833200 and 2012CB721100) of China (for W.L.), and by Grants-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science, and Technology of Japan (for I.A.).

Abstract

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Diversity-oriented biosynthesis of a library of antimycin-like compounds (380 altogether) was accomplished by using multiplex combinatorial biosynthesis. The core strategy depends on the use of combinatorial chemistry at different biosynthetic stages. This approach is applicable for the diversification of polyketides, nonribosomal peptides, and the hybrids that share a similar biosynthetic logic.

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