Site‐selective construction of N‐linked glycopeptides through photoredox catalysis DOI

Bingcheng Wei,

Ping Huang, Xinyao Wang

et al.

Angewandte Chemie, Journal Year: 2024, Volume and Issue: 137(3)

Published: Oct. 18, 2024

Abstract The glycosylation of peptides and proteins can significantly impact their intrinsic properties, such as conformation, stability, antigenicity, immunogenicity. Current methods for preparing N‐linked glycopeptides typically rely on amide bond formation, which be limited by the presence reactive functional groups like acids amines. Late‐stage functionalization offers a promising approach to obtaining glycopeptides. In this study, we demonstrate preparation through photoredox‐catalyzed site‐selective Giese addition between N‐glycosyl oxamic acid containing dehydroalanine (Dha) under visible light conditions. Unlike traditional that coupling aspartic glycosylamine, utilizes conjugation N‐glycosylated carbamoyl radicals with Dha, facilitating straightforward modification complex peptides.

Language: Английский

Chemoenzymatic Synthesis of Common Legionaminic Acid−Containing Pentasaccharide of Capsular Polysaccharides from Acinetobacter baumanniiK27 and K44† DOI

Jiarong Peng,

Tianhui Hao,

Wenjing Ma

et al.

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 16, 2024

Comprehensive Summary Acinetobacter baumannii infections pose a great threat to public health owing upsurging antibiotic resistance. Capsular polysaccharides (CPS) are major virulence determinants of pathogenic bacteria and have attracted much attention as potential targets for vaccine development. However, the obtainability structurally well‐defined CPS‐related oligosaccharides remains challenging. Herein, we report an efficient chemoenzymatic strategy first total synthesis common CPS pentasaccharide repeating unit K27 K44, containing difficult‐to‐construct α‐linked 5,7‐di‐ N ‐acetyllegionaminic acid (Leg5,7Ac 2 ) residue. The chemical branched tetrasaccharide precursor was accomplished by flexible orthogonal protecting‐group manipulations stereocontrolled glycosylations. Furthermore, enzyme‐catalyzed stereoselective installment legionaminic residue into tetrasaccharide, using one‐pot multienzyme (OPME) system produce sugar nucleotide CMP‐Leg5,7diN 3 subsequent α2,6‐sialyltransferase‐catalyzed glycosylation, achieved synthesize pentasaccharide.

Language: Английский

Citations

0
Generalizing a Ligation Site at the N-Glycosylation Sequon for Chemical Synthesis of N-Linked Glycopeptides and Glycoproteins DOI
Dongfang Li, Can Li, Qiushi Chen

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(42), P. 29017 - 29027

Published: Oct. 11, 2024

Chemical synthesis can generate homogeneous glycoproteins with well-defined and modifiable glycan structures at designated sites. The precision flexibility of the chemical synthetic approach provide a solution to heterogeneity problem glycopeptides/glycoproteins obtained through biological approaches. In this study, we reported that conserved

Language: Английский

Citations

0
Site‐selective construction of N‐linked glycopeptides through photoredox catalysis DOI

Bingcheng Wei,

Ping Huang, Xinyao Wang

et al.

Angewandte Chemie, Journal Year: 2024, Volume and Issue: 137(3)

Published: Oct. 18, 2024

Abstract The glycosylation of peptides and proteins can significantly impact their intrinsic properties, such as conformation, stability, antigenicity, immunogenicity. Current methods for preparing N‐linked glycopeptides typically rely on amide bond formation, which be limited by the presence reactive functional groups like acids amines. Late‐stage functionalization offers a promising approach to obtaining glycopeptides. In this study, we demonstrate preparation through photoredox‐catalyzed site‐selective Giese addition between N‐glycosyl oxamic acid containing dehydroalanine (Dha) under visible light conditions. Unlike traditional that coupling aspartic glycosylamine, utilizes conjugation N‐glycosylated carbamoyl radicals with Dha, facilitating straightforward modification complex peptides.

Language: Английский

Citations

0