| 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
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| 通讯作者 | Bai, LQ (reprint author), Shanghai Jiao Tong Univ, Sch Life Sci & Biotechnol, State Key Lab Microbial Metab, Shanghai 200240, Peoples R China |
| 2011-12-23 | |
| 发表期刊 | CHEMISTRY & BIOLOGY
 |
| ISSN | 1074-5521 |
| 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 |
| 学科领域 | Biochemistry & Molecular Biology |
| DOI | 10.1016/j.chembiol.2011.11.007 |
| 收录类别 | SCI |
| 语种 | 英语 |
| WOS记录号 | WOS:000298893900010 |
| 引用统计 | |
| 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 |
| 推荐引用方式 GB/T 7714 | 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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