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题名: Dual Carbamoylations on the Polyketide and Glycosyl Moiety by Asm21 Result in Extended Ansamitocin Biosynthesis
作者: null(李艳)1; Zhao, Peiji2; Kang, Qianjin1; Ma, Juan2; Bai, Linquan1; Deng, Zixin1
刊名: CHEMISTRY & BIOLOGY
关键词: ANTITUMOR AGENT ANSAMITOCIN ; BETA-LACTAM ANTIBIOTICS ; ACTINOSYNNEMA-PRETIOSUM ; GENE-CLUSTER ; DNA GYRASE ; CONCANAMYCIN-A ; STREPTOMYCES ; NOVOBIOCIN ; CARBAMOYLTRANSFERASE ; INHIBITORS
英文摘要: 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.
出版日期: 2011-12-23
卷号: 18, 期号:12, 页码:1571-1580
语种: 英语
收录类别: SCI
学科分类: Biochemistry & Molecular Biology
ISSN号: 1074-5521
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内容类型: 期刊论文
URI标识: http://ir.kib.ac.cn/handle/151853/14553
Appears in Collections:植物化学与西部植物资源持续利用国家重点实验室_期刊论文

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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

Recommended Citation:
Li, Y; Zhao, PJ; Kang, QJ; Ma, J; Bai, LQ; Deng, ZX.Dual Carbamoylations on the Polyketide and Glycosyl Moiety by Asm21 Result in Extended Ansamitocin Biosynthesis,CHEMISTRY & BIOLOGY,2011,18(12):1571-1580
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