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Longicatenamides A–D, Two Diastereomeric Pairs of Cyclic Hexapeptides Produced by Combined-culture of Streptomyces sp. KUSC_F05 and Tsukamurella pulmonis TP-B0596

The Journal of Antibiotics volume 74, pages 307–316 (2021)Cite this article

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Abstract

Longicatenamides A–D, two diastereomeric pairs of new cyclic hexapeptides, were isolated from the combined-culture of Streptomyces sp. KUSC_F05 and Tsukamurella pulmonis TP-B0596. Their planar structures were determined by spectroscopic analysis including extensive 2D NMR and MS analysis. The absolute configurations of their component amino acids were determined by the use of highly sensitive reagents we recently developed; the highly sensitive-advanced Marfey’s method (HS-advanced Marfey’s method), which led us to reduce the sample loss and prevent incorrect structural determination. Particularly, the Cβ-stereochemistry of hyGlu in longicatenamides A and C was assigned without any use of Cβ-Marfey’s methods. Longicatenamide A exhibited weak but preferential antimicrobial activity against Bacillus subtilis.

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Acknowledgements

This work was financially supported in part by a Grant-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science and Technology, Japan [17H06401 (H.K.), 18K14396 (T.K.), and 19H02840 (H.K.)], the Platform Project for Supporting Drug Discovery and Life Science Research from the Japan Agency for Medical Research and Development (AMED) [20am01092j0004 (H.K.)], Japan, and the Tokyo Biochemical Research Foundation (T.K.).

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Author notes

  1. Shan Lu

    Present address: Department of Chemistry, Biology and Marine Science, Faculty of Science, University of the Ryukyus, Okinawa, 903-0213, Japan

  2. These authors contributed equally: Yulu Jiang, Takumi Matsumoto

Authors and Affiliations

  1. Department of System Chemotherapy and Molecular Sciences, Division of Bioinformatics and Chemical Genomics, Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo-ku, Kyoto, 606-8501, Japan

    Yulu Jiang, Takumi Matsumoto, Takefumi Kuranaga, Shan Lu, Weicheng Wang & Hideaki Kakeya

  2. Department of Biotechnology, Graduate School of Agricultural and Life Sciences, The University of Tokyo, Bunkyo-ku, Tokyo, 113-8657, Japan

    Hiroyasu Onaka

  3. Collaborative Research Institute for Innovative Microbiology, The University of Tokyo, Bunkyo-ku, Tokyo, 113-8657, Japan

    Hiroyasu Onaka

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  1. Yulu Jiang
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Correspondence to Hideaki Kakeya.

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Jiang, Y., Matsumoto, T., Kuranaga, T. et al. Longicatenamides A–D, Two Diastereomeric Pairs of Cyclic Hexapeptides Produced by Combined-culture of Streptomyces sp. KUSC_F05 and Tsukamurella pulmonis TP-B0596. J Antibiot 74, 307–316 (2021). https://doi.org/10.1038/s41429-020-00400-3

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