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Mar. Drugs 2019, 17(3), 150; https://doi.org/10.3390/md17030150

Discovery of Stealthin Derivatives and Implication of the Amidotransferase FlsN3 in the Biosynthesis of Nitrogen-Containing Fluostatins

1
CAS Key Laboratory of Tropical Marine Bio-resources and Ecology, Guangdong Key Laboratory of Marine Materia Medica, RNAM Center for Marine Microbiology, Institutions of South China Sea Ecology and Environmental Engineering, South China Sea Institute of Oceanology, Chinese Academy of Sciences, 164 West Xingang Road, Guangzhou 510301, China
2
University of Chinese Academy of Sciences, 19 Yuquan Road, Beijing 100049, China
*
Author to whom correspondence should be addressed.
Received: 22 January 2019 / Revised: 15 February 2019 / Accepted: 27 February 2019 / Published: 4 March 2019
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Abstract

Diazobenzofluorene-containing atypical angucyclines exhibit promising biological activities. Here we report the inactivation of an amidotransferase-encoding gene flsN3 in Micromonospora rosaria SCSIO N160, a producer of fluostatins. Bioinformatics analysis indicated that FlsN3 was involved in the diazo formation. Chemical investigation of the flsN3-inactivation mutant resulted in the isolation of a variety of angucycline aromatic polyketides, including four racemic aminobenzo[b]fluorenes stealthins D–G (912) harboring a stealthin C-like core skeleton with an acetone or butanone-like side chain. Their structures were elucidated on the basis of nuclear magnetic resonance (NMR) spectroscopic data and X-ray diffraction analysis. A plausible mechanism for the formation of stealthins D–G (912) was proposed. These results suggested a functional role of FlsN3 in the formation/modification of N–N bond-containing fluostatins. View Full-Text
Keywords: angucyclines; N–N bond; raceme; gene inactivation; biosynthesis; marine; Micromonospora angucyclines; N–N bond; raceme; gene inactivation; biosynthesis; marine; Micromonospora
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Huang, C.; Yang, C.; Fang, Z.; Zhang, L.; Zhang, W.; Zhu, Y.; Zhang, C. Discovery of Stealthin Derivatives and Implication of the Amidotransferase FlsN3 in the Biosynthesis of Nitrogen-Containing Fluostatins. Mar. Drugs 2019, 17, 150.

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