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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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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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.
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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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DOI: https://doi.org/10.1038/nchembio.418
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