Recent Advances of 2‐Nitroglycals as Powerful Glycosyl Donors

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(18)

Published: March 2, 2024

Abstract 2‐Nitroglycals are important synthons for biological active 2‐aminoglycosides, glycoconjugates and natural products synthesis. Herein, we summarized the recent advances of 2‐nitroglycals including its synthetic methods applications. Using 2‐nitroglycals, nitro‐polyol derivatives, sugar‐furan sugar‐pyrrole molecules, 2,3‐diaminoglycosides 2‐amino‐1,3‐dithioglycosides were obtained via Michael–type addition, retro‐Henry‐type reaction, C1/C3‐Ferrier rearrangement [3+2] N ‐heterocyclic addition. Most these conversions achieved mild organo‐catalysis glycosylation methods.

Language: Английский

Synthesis and immunological study of tetrasaccharide repeating units of capsular polysaccharide of Group B Streptococcus serotype VIII and their protein conjugates

Journal of Carbohydrate Chemistry, Journal Year: 2024, Volume and Issue: unknown, P. 1 - 33

Published: Oct. 9, 2024

This study reports the efficient synthesis of three tetrasaccharide derivatives Group B Streptococcus (GBS) serotype VIII capsular polysaccharide with alternative glycan sequences and spacer chains through a convergent chemical glycosylation manner or one-pot three-enzyme assembly protocol. Using bifunctional glutarate ester as linker, these synthesized oligosaccharides were efficiently conjugated recombinant ScpA193 protein, generating resultant oligosaccharide-ScpA193 conjugates desirable carbohydrate loading. ELISA analysis antisera obtained from mice inoculated synthetic glycoconjugates showed elicitation strong oligosaccharide-specific immunoglobulin G (IgG) antibodies, suggesting potential for use in development GBS vaccines.

Language: Английский