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

Yunqin Zhang,

Leilei Wang,

Qingli Zhou

et al.

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(22)

Published: March 3, 2023

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 modular synthesis a tridecasaccharide vulgates through an orthogonal one-pot glycosylation strategy based on glycosyl ortho-(1-phenylvinyl)benzoates, which avoids issues thioglycoside-based synthesis. Our approach also features: 1) 5,7-O-di-tert-butylsilylene-directed stereoselective construction α-Kdo linkage; 2) hydrogen-bond-mediated aglycone delivery formation β-mannosidic bonds; 3) remote anchimeric assistance assembly α-fucosyl 4) several synthetic steps strategic use protecting groups streamline oligosaccharide assembly; 5) convergent [1+6+6] target.

Language: Английский

The Effect of Enteric-Derived Lipopolysaccharides on Obesity DOI Open Access
Kai Wang,

Weiwen Lai,

Tianqi Min

et al.

International Journal of Molecular Sciences, Journal Year: 2024, Volume and Issue: 25(8), P. 4305 - 4305

Published: April 13, 2024

Endotoxin is a general term for toxic substances in Gram-negative bacteria, whose damaging effects are mainly derived from the lipopolysaccharides (LPS) cell walls of and strong pyrogen. Obesity chronic, low-grade inflammatory condition, LPS thought to trigger exacerbate it. The gut flora largest source body, it increasingly believed that altered intestinal microorganisms can play an essential role pathology different diseases. Today, complex axis linking states adiposity has not been well elucidated. This review summarises evidence interconnection between LPS, obesity, flora, further expanding our understanding as mediator disease contributing lessening obesity related metabolic disorders. As providing targets associated with hoped interventions combine address individual differences treatment.

Language: Английский

Citations

8

Adipose triglyceride lipase suppresses noncanonical inflammasome by hydrolyzing LPS DOI
Weitao Li,

Qiannv Liu,

Yan Qian

et al.

Nature Chemical Biology, Journal Year: 2024, Volume and Issue: 20(11), P. 1434 - 1442

Published: Feb. 27, 2024

Language: Английский

Citations

7

Chemical Synthesis and Antigenic Evaluation of Inner Core Oligosaccharides from Acinetobacter baumannii Lipopolysaccharide DOI

Xian‐Yang Zhou,

Lingxin Li, Zhen Zhang

et al.

Angewandte Chemie International Edition, Journal Year: 2022, Volume and Issue: 61(29)

Published: May 11, 2022

Acinetobacter baumannii is currently posing a serious threat to global health. Lipopolysaccharide (LPS) potent virulence factor of pathogenic Gram-negative bacteria. To explore the antigenic properties A. LPS, four Kdo-containing inner core glycans from strain ATCC 17904 were synthesized. A flexible and divergent method based on use orthogonally substituted α-Kdo-(2→5)-Kdo disaccharides was developed. Selective removal different protecting groups in these key precursors elongation sugar chain via α-stereocontrolled coupling with 5,7-O-di-tert-butylsilylene or 5-O-benzoyl protected Kdo thioglycosides 2-azido-2-deoxyglucosyl thioglycoside allowed efficient assembly target molecules. Glycan microarray analysis sera infected patients revealed that 4,5-branched trimer potential epitope, which attractive for further immunological research develop carbohydrate vaccines against baumannii.

Language: Английский

Citations

28

Dually Amplified Electrochemical Aptasensor for Endotoxin Detection via Target-Assisted Electrochemically Mediated ATRP DOI
Qiong Hu,

Jianwen Wan,

Zhiwen Liang

et al.

Analytical Chemistry, Journal Year: 2023, Volume and Issue: 95(12), P. 5463 - 5469

Published: March 15, 2023

As the entering of bacterial endotoxin into blood can cause various life-threatening pathological conditions, screening and detection low-abundance are great importance to human health. Taking advantage signal amplification by target-assisted electrochemically mediated atom transfer radical polymerization (teATRP), we illustrate herein a simple cost-effective electrochemical aptasensor capable detecting with high sensitivity selectivity. Specifically, aptamer receptor was employed for selective capture endotoxin, which glycan chain then decorated ATRP initiators via covalent coupling between diol sites phenylboronic acid (PBA) group, followed recruitment ferrocene reporters grafting polymer chains through potentiostatic eATRP under ambient temperature. be hundreds while further recruit thousands each initiator-decorated site, teATRP-based strategy allows dual signal. This dually amplified has ability sensitively selectively detect at concentration as low 1.2 fg/mL, its practical applicability been demonstrated using serum samples. Owing simplicity, efficiency, biocompatibility, inexpensiveness strategy, this holds application potential in sensitive many other chain-containing bio-targets.

Language: Английский

Citations

15

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

Yunqin Zhang,

Leilei Wang,

Qingli Zhou

et al.

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(22)

Published: March 3, 2023

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 modular synthesis a tridecasaccharide vulgates through an orthogonal one-pot glycosylation strategy based on glycosyl ortho-(1-phenylvinyl)benzoates, which avoids issues thioglycoside-based synthesis. Our approach also features: 1) 5,7-O-di-tert-butylsilylene-directed stereoselective construction α-Kdo linkage; 2) hydrogen-bond-mediated aglycone delivery formation β-mannosidic bonds; 3) remote anchimeric assistance assembly α-fucosyl 4) several synthetic steps strategic use protecting groups streamline oligosaccharide assembly; 5) convergent [1+6+6] target.

Language: Английский

Citations

14