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Structural Basis of Low-Molecular-Weight Thiol Glycosylation in Lincomycin A Biosynthesis.
Dai, Yuhan; Cheng, Yiyuan; Ding, Weizhong; Qiao, Hang; Zhang, Derundong; Zhong, Guannan; Xia, Mingyu; Tao, Jiang; Sun, Peng; Fang, Pengfei; Liu, Wen.
Afiliación
  • Dai Y; Henan Institute of Advanced Technology, Zhengzhou University, Zhengzhou 450052, China.
  • Cheng Y; State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Shanghai 200032, China.
  • Ding W; State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Shanghai 200032, China.
  • Qiao H; State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Shanghai 200032, China.
  • Zhang D; Department of Chemistry, University of Science and Technology of China, 96 Jinzhai Road, Hefei, Anhui 230026, China.
  • Zhong G; State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Shanghai 200032, China.
  • Xia M; State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Shanghai 200032, China.
  • Tao J; State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Shanghai 200032, China.
  • Sun P; State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Shanghai 200032, China.
  • Fang P; Department of General Dentistry, Ninth People's Hospital, Shanghai Jiao Tong University School of Medicine, 639 Zhizaoju Road, Shanghai 200011, China.
  • Liu W; School of Pharmacy, Naval Medical University, 325 Guohe Road, Shanghai 200433, China.
ACS Chem Biol ; 18(6): 1271-1277, 2023 06 16.
Article en En | MEDLINE | ID: mdl-37272735
The involvement of low-molecular-weight thiols in the biosynthesis of natural products is rarely reported. During lincomycin A biosynthesis, ergothioneine (EGT) is incorporated in the S-glycosylation catalyzed by LmbT. In contrast to the widely reported glycosylation of nitrogen and oxygen atoms, the glycosylation of sulfur atoms is less studied. In particular, the crystal structure of enzymes that glycosylate thiols on small molecules rather than peptides has not been reported. Here, we report the crystal structures of LmbT in apo form and in complex with GDP and EGT S-conjugated lincosamine. We found that LmbT has a characteristic glycosyltransferase type B fold, which forms a symmetric homotetramer. The substrates are bound deeply in the catalytic cleft. Consistent with the substrate structure, LmbT does not have the large peptide binding groove of the previously reported S-glycosyltransferase. Combined with site-directed mutagenesis, we propose a catalytic mechanism for the unusual EGT-mediated S-glycosylation in natural product biosynthesis.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Lincomicina / Ergotioneína Idioma: En Revista: ACS Chem Biol Año: 2023 Tipo del documento: Article País de afiliación: China Pais de publicación: Estados Unidos
Texto completo
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Imprimir
XML
PubMed Links
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Lincomicina / Ergotioneína Idioma: En Revista: ACS Chem Biol Año: 2023 Tipo del documento: Article País de afiliación: China Pais de publicación: Estados Unidos