Synthesis of Campylobacter jejuni capsular oligosaccharides and identification of a potential O -antigen against campylobacteriosis DOI
Jianjun Wang, Xuemei Yang, Zirong Huang

et al.

Science Advances, Journal Year: 2025, Volume and Issue: 11(15)

Published: April 9, 2025

The vaccines against campylobacteriosis are urgently needed because of the rising multidrug resistance pathogenic Campylobacter jejuni . capsular polysaccharides these bacteria, containing unique 6-deoxy-β- d - ido -heptopyranosyl or l glycero -β- residues, have emerged as attractive antigens. Expeditious assembly oligosaccharides derived from glycans is challenging β- -idopyranosidic linkages formidable to directly construct. Furthermore, whether synthetic C. could induce sufficient immunogenicity potential antigens remains unexplored. Here, we report a protocol for forming bonds using α- -6-deoxy- -heptopyranosyl, -idopyranosyl, and -/ -α- ortho -hexynylbenzoates glycosylating agents under gold(I) catalysis. To demonstrate versatility methods, concise synthesis conjugatable di-/tetra-/hexa-/octasaccharides, having backbone [→3)-6-deoxy-β- -heptopyranosyl-(1→4)-2-acetamido-2-deoxy-β- -glucopyranosyl-(1→], has been achieved. assessment glycoconjugates, prepared by conjugating synthesized cross-reactive material 197, reveals disaccharide O -antigen developing campylobacteriosis. This work should facilitate development infections.

Language: Английский

Triflic Acid‐Catalyzed Dehydrative Amination of 2‐Arylethanols with Weak N‐Nucleophiles in Hexafluoroisopropanol DOI Creative Commons
Max Van Hoof, Robert J. Mayer, Joseph Moran

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 21, 2024

Abstract The catalytic deoxyamination of readily available 2‐arylethanols offers an appealing, simple, and straightforward means accessing β‐(hetero)arylethylamines biological interest. Yet, it currently represents a great challenge to synthetic chemistry. In most cases, the alcohol has be either pre‐activated in situ or converted into reactive carbonyl intermediate, limiting substrate scope for some methods. Examples direct dehydrative amination are thus still scarce. Here, we describe protocol based on synergy triflic acid hexafluoroisopropanol, which enables stereospecific broad array 2‐arylethanols, does not require any pre‐activation alcohol. This approach yields high value‐added products incorporating sulfonamide, amide, urea, aniline functionalities. addition, this was applied sulfidation 2‐arylethanols. Mechanistic experiments DFT computations indicate formation phenonium ions as key intermediates reaction.

Language: Английский

Citations

5
Strong Hydrogen Bond Donating Solvents Accelerate the Passerini Three-Component Reaction DOI Creative Commons
Claudio Ferdeghini, Minghui Wu, Prabhat Ranjan

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: April 3, 2025

We report enhanced reaction rates of the Passerini (P-3CR) using 1,1,1,3,3,3-hexafluoroisopropanol (HFIP) as a cosolvent. Although alcoholic solvents typically increase energy barrier rate-determining step for P-3CR, we observed significant rate enhancements even when employing strong hydrogen bond donating (HBD) alcohols cosolvents. This enhancement was most aprotic organic solvents, with exception accepting (HBA) such DMF. Experimental kinetic studies and DFT calculations provided mechanistic rationale our observations. An investigation substrate scope showed that this generally resulted in (slight) overall yield P-3CR.

Language: Английский

Citations

0
Synthesis of Campylobacter jejuni capsular oligosaccharides and identification of a potential O -antigen against campylobacteriosis DOI
Jianjun Wang, Xuemei Yang, Zirong Huang

et al.

Science Advances, Journal Year: 2025, Volume and Issue: 11(15)

Published: April 9, 2025

The vaccines against campylobacteriosis are urgently needed because of the rising multidrug resistance pathogenic Campylobacter jejuni . capsular polysaccharides these bacteria, containing unique 6-deoxy-β- d - ido -heptopyranosyl or l glycero -β- residues, have emerged as attractive antigens. Expeditious assembly oligosaccharides derived from glycans is challenging β- -idopyranosidic linkages formidable to directly construct. Furthermore, whether synthetic C. could induce sufficient immunogenicity potential antigens remains unexplored. Here, we report a protocol for forming bonds using α- -6-deoxy- -heptopyranosyl, -idopyranosyl, and -/ -α- ortho -hexynylbenzoates glycosylating agents under gold(I) catalysis. To demonstrate versatility methods, concise synthesis conjugatable di-/tetra-/hexa-/octasaccharides, having backbone [→3)-6-deoxy-β- -heptopyranosyl-(1→4)-2-acetamido-2-deoxy-β- -glucopyranosyl-(1→], has been achieved. assessment glycoconjugates, prepared by conjugating synthesized cross-reactive material 197, reveals disaccharide O -antigen developing campylobacteriosis. This work should facilitate development infections.

Language: Английский

Citations

0