Dual Carbamoylations on the Polyketide and Glycosyl Moiety by Asm21 Result in Extended Ansamitocin Biosynthesis
Li, Yan1; Zhao, Peiji2; Kang, Qianjin1; Ma, Juan2; Bai, Linquan1; Deng, Zixin1
2011-12-23
发表期刊CHEMISTRY & BIOLOGY
ISSN1074-5521
卷号18期号:12页码:1571-1580
摘要Carbamoylation is one of the post-PKS modifications in ansamitocin biosynthesis. A novel ansamitocinoside with carbamoyl substitution at the C-4 hydroxyl group of the N-beta-D-glucosyl moiety was identified from the ansamitocin producer, Actinosynnema pretiosum. Through biotransformation, the carbamoyltransferase gene asm21 was suggested to be responsible for the carbamoylation of the glucosyl moiety. Three new derivatives without the backbone carbamoyl group were isolated from an asm21 mutant and characterized by NMR spectroscopy. Among them, 18-O-methyl-19-chloroproansamitocin was the major product and the preferred substrate for macrolactam C-7 carbamoylation by Asm21. However, Asm21 exhibited higher catalytic efficiency toward the glucosyl moiety. Furthermore, the dual carbamoylations and N-glycosylation were precisely demonstrated in vivo. This work represents the first biochemical characterization of an O-carbamoyltransferase performing dual actions on both a polyketide backbone and a glycosyl moiety during ansamitocin biosynthesis.
关键词Antitumor Agent Ansamitocin Beta-lactam Antibiotics Actinosynnema-pretiosum Gene-cluster Dna Gyrase Concanamycin-a Streptomyces Novobiocin Carbamoyltransferase Inhibitors
资助信息National Natural Science Foundation of China; Ministry of Science and Technology; Ministry of Education; Shanghai Municipality
学科领域Biochemistry & Molecular Biology
DOI10.1016/j.chembiol.2011.11.007
收录类别SCI
语种英语
WOS研究方向Biochemistry & Molecular Biology
WOS类目Biochemistry & Molecular Biology
WOS记录号WOS:000298893900010
引用统计
被引频次:5[WOS]   [WOS记录]     [WOS相关记录]
文献类型期刊论文
条目标识符http://ir.kib.ac.cn/handle/151853/14553
专题植物化学与西部植物资源持续利用国家重点实验室
作者单位1.Shanghai Jiao Tong Univ, Sch Life Sci & Biotechnol, State Key Lab Microbial Metab, Shanghai 200240, Peoples R China
2.Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources W China, Kunming 650204, Peoples R China
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Li, Yan,Zhao, Peiji,Kang, Qianjin,et al. Dual Carbamoylations on the Polyketide and Glycosyl Moiety by Asm21 Result in Extended Ansamitocin Biosynthesis[J]. CHEMISTRY & BIOLOGY,2011,18(12):1571-1580.
APA Li, Yan,Zhao, Peiji,Kang, Qianjin,Ma, Juan,Bai, Linquan,&Deng, Zixin.(2011).Dual Carbamoylations on the Polyketide and Glycosyl Moiety by Asm21 Result in Extended Ansamitocin Biosynthesis.CHEMISTRY & BIOLOGY,18(12),1571-1580.
MLA Li, Yan,et al."Dual Carbamoylations on the Polyketide and Glycosyl Moiety by Asm21 Result in Extended Ansamitocin Biosynthesis".CHEMISTRY & BIOLOGY 18.12(2011):1571-1580.
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