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A copper-containing oxidase catalyzes C-nitrosation in nitrosobenzamide biosynthesis

Nature Chemical Biology volume 6, pages 641–643 (2010)Cite this article

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Abstract

Although C-nitroso aromatic compounds have several bioactivities of medicinal interest, the biosynthetic enzymes involved in C-nitrosation have remained unknown until now. Here, we report the entire biosynthesis pathway of 4-hydroxy-3-nitrosobenzamide in Streptomyces murayamaensis, in which a tyrosinase-like copper-containing monooxygenase is responsible for the C-nitrosation. This finding indicates diverse catalytic functions of tyrosinase-like copper-containing monooxygenases in nature.

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Figure 1
Figure 2: Biosynthesis of 4,3-HNBAm in vivo and in vitro.
Figure 3: Biosynthetic pathway to 4,3-HNBAm.

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Acknowledgements

This work was supported, in part, by a research grant from the New Energy and Industrial Technology Development Organization of Japan, by a Grant-in-Aid for Scientific Research (C) from the Ministry of Education, Culture, Sports, Science and Technology of Japan and by the Targeted Proteins Research Program of the Ministry of Education, Culture, Sports, Science and Technology of Japan.

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Author notes

  1. Sueharu Horinouchi: Deceased 12 July 2009.

Authors and Affiliations

  1. Department of Biotechnology, Graduate School of Agriculture and Life Sciences, University of Tokyo, Tokyo, Japan

    Akio Noguchi, Takeshi Kitamura, Sueharu Horinouchi & Yasuo Ohnishi

  2. Biotechnology Research Center, Toyama Prefectural University, Toyama, Japan

    Hiroyasu Onaka

Authors
  1. Akio Noguchi
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  2. Takeshi Kitamura
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  3. Hiroyasu Onaka
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  4. Sueharu Horinouchi
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  5. Yasuo Ohnishi
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Contributions

A.N. characterized the gene cluster and performed the enzyme assay; T.K. cloned the gene cluster. H.O. supervised the construction of the cosmid library, and S.H. and Y.O. supervised the overall project. Y.O. was responsible for project planning and design, and, with A.N., wrote the manuscript.

Corresponding author

Correspondence to Yasuo Ohnishi.

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The authors declare no competing financial interests.

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Supplementary Methods, Figures 1–7, Tables 1–3 (PDF 4976 kb)

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Noguchi, A., Kitamura, T., Onaka, H. et al. A copper-containing oxidase catalyzes C-nitrosation in nitrosobenzamide biosynthesis. Nat Chem Biol 6, 641–643 (2010). https://doi.org/10.1038/nchembio.418

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