One-Pot Assembly of Mannose-Capped Lipoarabinomannan Motifs up to 101-Mer from the Mycobacterium tuberculosis Cell Wall

doi:10.1021/jacs.3c12815

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	One-Pot Assembly of Mannose-Capped Lipoarabinomannan Motifs up to 101-Mer from the Mycobacterium tuberculosis Cell Wall
	Ma, Yuxin; Zhang, Yunqin; Huang, Yingying; Chen, Zixi; Xian, Qingyun; Su, Rui; Jiang, Qiong; Wang, Xiufang; Xiao, Guozhi
	2024
发表期刊	JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
ISSN	0002-7863
卷号	146 期号:6 页码:4112-4122
摘要	Lipoarabinomannan (LAM) from the Mycobacterium tuberculosis cell envelope represents important targets for the development of new therapeutic agents against tuberculosis, which is a deadly disease that has plagued mankind for a long time. However, the accessibility of long, branched, and complex lipoarabinomannan over 100-mer remains a long-standing challenge. Herein, we report the modular synthesis of mannose-capped lipoarabinomannan 101-mer from the M. tuberculosis cell wall using a one-pot assembly strategy on the basis of glycosyl ortho-(1-phenylvinyl)benzoates (PVB), which not only accelerates the modular synthesis but also precludes the potential problems associated with one-pot glycosylation with thioglycosides. Shorter sequences including 18-mer, 19-mer, and 27-mer are also synthesized for in-depth structure-activity relationship biological studies. Current synthetic routes also highlight the following features: (1) streamlined synthesis of various linear and branched glycans using one-pot orthogonal glycosylation on the combination of glycosyl N-phenyltrifluoroacetimidates, glycosyl ortho-alkynylbenzoates, and glycosyl PVB; (2) highly stereoselective construction of 10 1,2-cis-arabinofuranosyl linkages using 5-O-(2-quinolinecarbonyl)-directing 1,2-cis-arabinofuranosylation via a hydrogen-bond-mediated aglycone delivery strategy; and (3) convergent [(18 + 19) x 2 + 27] one-pot synthesis of the 101-mer LAM polysaccharide. The present work demonstrates that this orthogonal one-pot glycosylation strategy can highly streamline the chemical synthesis of long, branched, and complex polysaccharides.
DOI	10.1021/jacs.3c12815
WOS记录号	WOS:001162255800001
引用统计
文献类型	期刊论文
条目标识符	http://ir.kib.ac.cn/handle/151853/76252
专题	中国科学院昆明植物研究所
推荐引用方式 GB/T 7714	Ma, Yuxin,Zhang, Yunqin,Huang, Yingying,et al. One-Pot Assembly of Mannose-Capped Lipoarabinomannan Motifs up to 101-Mer from the Mycobacterium tuberculosis Cell Wall[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,2024,146(6):4112-4122.
APA	Ma, Yuxin.,Zhang, Yunqin.,Huang, Yingying.,Chen, Zixi.,Xian, Qingyun.,...&Xiao, Guozhi.(2024).One-Pot Assembly of Mannose-Capped Lipoarabinomannan Motifs up to 101-Mer from the Mycobacterium tuberculosis Cell Wall.JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,146(6),4112-4122.
MLA	Ma, Yuxin,et al."One-Pot Assembly of Mannose-Capped Lipoarabinomannan Motifs up to 101-Mer from the Mycobacterium tuberculosis Cell Wall".JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 146.6(2024):4112-4122.

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