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Quinomycins with an unusual N-methyl-3-methylsulfinyl-alanine residue from a Streptomyces sp

The Journal of Antibiotics (2024)Cite this article

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Abstract

Four new echinomycin congeners, quinomycins M−P (1−4) were isolated from the cultures of the soil-derived Streptomyces sp. CPCC205575. The planar structures were determined by comprehensive analyses of NMR and HRESIMS/MS data. The absolute configurations were elucidated by the advanced Marfey’s method combined with biosynthetic gene analysis. Compounds 1−4 represent the first examples of quinomycin-type natural products with the sulfur atom at the N,S-dimethylcysteine residue oxidized as a sulfoxide group forming the unusual N-methyl-3-methylsulfinyl-alanine residue. Bioassay results revealed that the oxidation of the sulfur atom at the Cys or Cys′ residues led to dramatic decrease of cytotoxicity and antimicrobial activity.

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Acknowledgements

This work was financially supported by the National Natural Science Foundation of China (Grant no. 82273830) and CAMS Innovation Fund for Medical Sciences (CIFMS, 2021-I2M-1-055).

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Authors and Affiliations

  1. Institute of Medicinal Biotechnology, Chinese Academy of Medical Sciences and Peking Union Medical College, 100050, Beijing, PR China

    Anqi Wang, Shasha Li, Yuanjuan Wei, Guiyang Wang, Wenjing Shi, Yue Shang, Liyan Yu, Shuzhen Chen, Yan Li & Maoluo Gan

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Correspondence to Shuzhen Chen, Yan Li or Maoluo Gan.

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Wang, A., Li, S., Wei, Y. et al. Quinomycins with an unusual N-methyl-3-methylsulfinyl-alanine residue from a Streptomyces sp. J Antibiot (2024). https://doi.org/10.1038/s41429-024-00736-0

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