Discovery of glycosylated naphthacemycins and elucidation of the glycosylation

Yu-Hang Gao; Qiu-Yue Nie; Yu Hu; Xinhua Lu; Wensheng Xiang; Xiangjing Wang; Gong-Li Tang

doi:10.1016/j.bbrc.2022.06.095

Discovery of glycosylated naphthacemycins and elucidation of the glycosylation

Biochem Biophys Res Commun. 2022 Sep 24:622:122-128. doi: 10.1016/j.bbrc.2022.06.095. Epub 2022 Jul 9.

Authors

Yu-Hang Gao¹, Qiu-Yue Nie², Yu Hu³, Xinhua Lu⁴, Wensheng Xiang¹, Xiangjing Wang⁵, Gong-Li Tang⁶

Affiliations

¹ Key Laboratory of Agriculture Biological Functional Gene of Heilongjiang Provincial Education Committee, Northeast Agricultural University, No. 600 Changjiang Road, Xiangfang District, Harbin, 150030, PR China.
² State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, PR China. Electronic address: [email protected].
³ State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, PR China.
⁴ New Drug Research and Development Center, North China Pharmaceutical Group Corporation, National Microbial Medicine Engineering and Research Center, Hebei Industry Microbial Metabolic Engineering & Technology Research Center, Key Laboratory New Drug Screening Technology of Shijiazhuang City, Shijiazhuang, 050015, PR China.
⁵ Key Laboratory of Agriculture Biological Functional Gene of Heilongjiang Provincial Education Committee, Northeast Agricultural University, No. 600 Changjiang Road, Xiangfang District, Harbin, 150030, PR China. Electronic address: [email protected].
⁶ State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, PR China; School of Chemistry and Materials Science Hangzhou Institute for Advanced Study, University of Chinese Academy of Sciences, 1 Sub-lane Xiangshan, Hangzhou, 310024, PR China. Electronic address: [email protected].

PMID: 35849953
DOI: 10.1016/j.bbrc.2022.06.095

Abstract

Two glycosylated naphthacemycins (naphthacemycins D₁ and D₂) were identified in Streptomyces sp. N12W1565. These two compounds not only showed antimicrobial potential against bacteria but also exhibited more aqueous solubility than naphthacemycins. Furthermore, the whole genome of Streptomyces sp. N12W1565 has been sequenced, the natY gene, located outside the biosynthetic gene cluster encoding a D-glucose glycosyltransferase, was identified to mediate glycosylation in the phenolic hydroxyl of the naphthacemycin core scaffold. Glycosyltransferase was elucidated in vitro by using a homologous enzyme, which showed potential as a biocatalyst.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Anti-Bacterial Agents / pharmacology
Glycosylation
Glycosyltransferases / genetics
Glycosyltransferases / metabolism
Multigene Family
Streptomyces*

Substances

Anti-Bacterial Agents
Glycosyltransferases