An orthogonal and reactivity-based one-pot glycosylation strategy for both glycan and nucleoside synthesis: access to TMG-chitotriomycin, lipochitooligosaccharides and capuramycin

doi:10.1039/d0sc06815b

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	An orthogonal and reactivity-based one-pot glycosylation strategy for both glycan and nucleoside synthesis: access to TMG-chitotriomycin, lipochitooligosaccharides and capuramycin
	He,Haiqing; Xu,Lili; Sun,Roujing; Zhang,Yunqin; Huang,Yingying; Chen,Zixi; Li,Penghua; Yang,Rui; Xiao,Guozhi
	2021
发表期刊	CHEMICAL SCIENCE
ISSN	2041-6520
卷号	12 期号:14 页码:5143-5151
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.
关键词	EFFICIENT SYNTHESIS RHIZOBIUM-MELILOTI OLIGOSACCHARIDE GLYCOSIDES VERSATILE DONORS CANCER CHITOOLIGOSACCHARIDES TRICHLOROACETIMIDATE THIOGLYCOSIDES
DOI	10.1039/d0sc06815b
WOS记录号	WOS:000640322400013
引用统计
文献类型	期刊论文
条目标识符	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.

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