An orthogonal and reactivity-based one-pot glycosylation strategy for both glycan and nucleoside synthesis: access to TMG-chitotriomycin, lipochitooligosaccharides and capuramycin
文献类型：期刊论文
| 作者 | He,Haiqing; Xu,Lili; Sun,Roujing; Zhang,Yunqin; Huang,Yingying; Chen,Zixi; Li,Penghua ; Yang,Rui; Xiao,Guozhi
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| 刊名 | CHEMICAL SCIENCE
 |
| 出版日期 | 2021 |
| 卷号 | 12期号:14页码:5143-5151 |
| ISSN号 | 2041-6520 |
| 关键词 | EFFICIENT SYNTHESIS RHIZOBIUM-MELILOTI OLIGOSACCHARIDE GLYCOSIDES VERSATILE DONORS CANCER CHITOOLIGOSACCHARIDES TRICHLOROACETIMIDATE THIOGLYCOSIDES |
| DOI | 10.1039/d0sc06815b |
| 英文摘要 | Both glycans (O-glycosides) and nucleosides (N-glycosides) play important roles in numerous biological processes. Chemical synthesis is a reliable and effective means to solve the attainability issues of these essential biomolecules. However, due to the stereo- and regiochemical issues during glycan assembly, together with problems including the poor solubility and nucleophilicity of nucleobases in nucleoside synthesis, the development of one-pot glycosylation strategies toward efficient synthesis of both glycans and nucleosides remains poor and challenging. Here, we report the first orthogonal and reactivity-based one-pot glycosylation strategy suitable for both glycan and nucleoside synthesis on the basis of glycosyl ortho-(1-phenylvinyl)benzoates. This one-pot glycosylation strategy not only inherits the advantages including no aglycon transfers, no undesired interference of departing species, and no unpleasant odors associated with the previously developed orthogonal one-pot glycosylation strategy based on glycosyl ortho-alkynylbenzoates, but also highly expands the scope (glycans and nucleosides) and increases the number of leaving groups that could be employed for the multistep one-pot synthesis (up to the formation of four different glycosidic bonds). In particular, the current one-pot glycosylation strategy is successfully applied to the total synthesis of a promising tuberculosis drug lead capuramycin and the divergent and formal synthesis of TMG-chitotriomycin with potent and specific inhibition activities toward beta -N-acetylglucosaminidases and important endosymbiotic lipochitooligosaccharides including the Nod factor and the Myc factor, which represents one of the most efficient and straightforward synthetic routes toward these biologically salient molecules. |
| WOS记录号 | WOS:000640322400013 |
| 源URL | [http://ir.kib.ac.cn/handle/151853/73193]  |
| 专题 | 中国科学院昆明植物研究所 |
| 作者单位 | Chinese Acad Sci, Univ Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources West Ch, Kunming 650201, Yunnan, Peoples R China |
| 推荐引用方式 GB/T 7714 | He,Haiqing,Xu,Lili,Sun,Roujing,et al. An orthogonal and reactivity-based one-pot glycosylation strategy for both glycan and nucleoside synthesis: access to TMG-chitotriomycin, lipochitooligosaccharides and capuramycin[J]. CHEMICAL SCIENCE,2021,12(14):5143-5151. |
| APA | He,Haiqing.,Xu,Lili.,Sun,Roujing.,Zhang,Yunqin.,Huang,Yingying.,...&Xiao,Guozhi.(2021).An orthogonal and reactivity-based one-pot glycosylation strategy for both glycan and nucleoside synthesis: access to TMG-chitotriomycin, lipochitooligosaccharides and capuramycin.CHEMICAL SCIENCE,12(14),5143-5151. |
| MLA | He,Haiqing,et al."An orthogonal and reactivity-based one-pot glycosylation strategy for both glycan and nucleoside synthesis: access to TMG-chitotriomycin, lipochitooligosaccharides and capuramycin".CHEMICAL SCIENCE 12.14(2021):5143-5151. |
入库方式： OAI收割
来源：昆明植物研究所
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