Modular Synthesis of a Tridecasaccharide Motif of Bacteroides vulgatus Lipopolysaccharides against Inflammatory Bowel Diseases through an Orthogonal One-Pot Glycosylation Strategy

doi:10.1002/anie.202301351

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	Modular Synthesis of a Tridecasaccharide Motif of Bacteroides vulgatus Lipopolysaccharides against Inflammatory Bowel Diseases through an Orthogonal One-Pot Glycosylation Strategy
	Zhang,Yunqin; Wang,Leilei; Zhou,Qingli; Li,Zuoshan; Li,Dan; Yin,Caixia; Wang,Xiufang; Xiao,Guozhi
	2023
发表期刊	ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
ISSN	1521-3773
摘要	Lipopolysaccharides from Bacteroides vulgatus represent interesting targets for the treatment of inflammatory bowel diseases. However, efficient access to long, branched and complex lipopolysaccharides remains challenging. Herein, we report the modular synthesis of a tridecasaccharide from Bacteroides vulgates through an orthogonal one-pot glycosylation strategy based on glycosyl ortho-(1-phenylvinyl)benzoates, which avoids the issues of thioglycoside-based one-pot synthesis. Our approach also features: 1) 5,7-O-di-tert-butylsilylene-directed glycosylation for stereoselective construction of the alpha-Kdo linkage; 2) hydrogen-bond-mediated aglycone delivery for the stereoselective formation of beta-mannosidic bonds; 3) remote anchimeric assistance for stereoselective assembly of the alpha-fucosyl linkage; 4) several orthogonal one-pot synthetic steps and strategic use of orthogonal protecting groups to streamline oligosaccharide assembly; 5) convergent [1+6+6] one-pot synthesis of the target.
关键词	Anti-Inflammatory Activity Lipopolysaccharides Oligosaccharide Synthesis Orthogonal One-Pot Glycosylation Stereoselectivity STEREOSELECTIVE-SYNTHESIS CHEMICAL-SYNTHESIS ACID DONORS ALKYNYLBENZOATES GLYCOSIDES DISCOVERY CATALYSIS GLYCANS FOCUS
学科领域	Chemistry
DOI	10.1002/anie.202301351
收录类别	SCI
WOS记录号	WOS:000955157800001
引用统计
文献类型	期刊论文
条目标识符	http://ir.kib.ac.cn/handle/151853/75551
专题	中国科学院昆明植物研究所
推荐引用方式 GB/T 7714	Zhang,Yunqin,Wang,Leilei,Zhou,Qingli,et al. Modular Synthesis of a Tridecasaccharide Motif of Bacteroides vulgatus Lipopolysaccharides against Inflammatory Bowel Diseases through an Orthogonal One-Pot Glycosylation Strategy[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2023.
APA	Zhang,Yunqin.,Wang,Leilei.,Zhou,Qingli.,Li,Zuoshan.,Li,Dan.,...&Xiao,Guozhi.(2023).Modular Synthesis of a Tridecasaccharide Motif of Bacteroides vulgatus Lipopolysaccharides against Inflammatory Bowel Diseases through an Orthogonal One-Pot Glycosylation Strategy.ANGEWANDTE CHEMIE-INTERNATIONAL EDITION.
MLA	Zhang,Yunqin,et al."Modular Synthesis of a Tridecasaccharide Motif of Bacteroides vulgatus Lipopolysaccharides against Inflammatory Bowel Diseases through an Orthogonal One-Pot Glycosylation Strategy".ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2023).

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