Ribosomal Synthesis of Backbone-Macrocyclic Peptides Containing γ-Amino Acids

Authors

  • Yukinori Ohshiro,

    1. Department of Advanced Interdisciplinary Studies, Graduate School of Engineering, The University of Tokyo, 4-6-1, Komaba, Meguro, Tokyo 153-8904 (Japan)
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  • Dr. Eiji Nakajima,

    1. Department of Chemistry and Biotechnology, Graduate School of Engineering, The University of Tokyo, 7-3-1, Hongo, Bunkyo, Tokyo 113-8656 (Japan)
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  • Dr. Yuki Goto,

    1. Department of Chemistry, Graduate School of Science, The University of Tokyo, 7-3-1, Hongo, Bunkyo, Tokyo 113-0033 (Japan), Fax: (+81) 3-5841-8372
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  • Dr. Shinichiro Fuse,

    1. Department of Applied Chemistry, Tokyo Institute of Technology, 2-12-1, Ookayama, Meguro, Tokyo 152-8552 (Japan)
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  • Prof. Dr. Takashi Takahashi,

    1. Department of Applied Chemistry, Tokyo Institute of Technology, 2-12-1, Ookayama, Meguro, Tokyo 152-8552 (Japan)
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  • Prof. Dr. Takayuki Doi,

    1. Graduate School of Pharmaceutical Sciences, Tohoku University, 6-3, Aza-aoba, Aramaki, Aoba, Sendai, Miyagi 980-8578 (Japan)
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  • Prof. Dr. Hiroaki Suga

    Corresponding author
    1. Department of Chemistry, Graduate School of Science, The University of Tokyo, 7-3-1, Hongo, Bunkyo, Tokyo 113-0033 (Japan), Fax: (+81) 3-5841-8372
    2. Department of Advanced Interdisciplinary Studies, Graduate School of Engineering, The University of Tokyo, 4-6-1, Komaba, Meguro, Tokyo 153-8904 (Japan)
    3. Department of Chemistry and Biotechnology, Graduate School of Engineering, The University of Tokyo, 7-3-1, Hongo, Bunkyo, Tokyo 113-8656 (Japan)
    4. WCU Department of Molecular Medicine and Biopharmaceutical Sciences, Seoul National University, Seoul 151-742 (Korea)
    • Department of Chemistry, Graduate School of Science, The University of Tokyo, 7-3-1, Hongo, Bunkyo, Tokyo 113-0033 (Japan), Fax: (+81) 3-5841-8372
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Abstract

original image

Mine's in the middle: We report here a novel methodology for the ribosomal synthesis of backbone-macrocyclic peptides containing γ-amino acids under the reprogrammed genetic code. Integration of reprogrammed initiation by using exotic dipeptides with C-terminal diketopiperadine-thioester formation has successfully afforded backbone-cyclized peptides with γ-amino acids at an internal position.

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