A Potentially Valuable Advance in the Synthesis of Carbohydrate-Based Anticancer Vaccines through Extended Cycloaddition Chemistry

2006/09/09 by Qian Wan, Jiehao Chen, Gong Chen +1 · 97 citations
Biochemistry, Genetics and Molecular Biology · Chemistry · #Azide #Biochemistry #Carbohydrate #Carbohydrate Chemistry and Synthesis #Catalysis #Chemistry #Click Chemistry and Applications #Click chemistry #Combinatorial chemistry #Cycloaddition #Glycosylation and Glycoproteins Research #Oligosaccharide #Organic chemistry #Peptide

paper · doi:10.1021/jo061406i

published in The Journal of Organic Chemistry 71(21), 8244-8249 (American Chemical Society)

openalex publication_date 2006/09/09 · openalex created_date 2025/10/10 · openalex updated_date 2026/08/01

Abstract

An advance in the long-term problem of joining complex oligosaccharides to polypeptides and even proteins is described herein. The key method involves equipping the oligosaccharide sector with an azide and the polypeptide with pendant alkynyl functionality. The two sectors are joined through a "click-like" cycloaddition. The method encompasses oligosaccharide constructs with several azide linkages which undergo concurrent cycloaddition to peptide-based acetylenes. This technology could well prove to be useful in the construction of fully synthetic vaccines.

Citations

• Activity-Based Protein Profiling in Vivo Using a Copper(I)-Catalyzed Azide-Alkyne [3 + 2] Cycloaddition

Cited by

• Cu(I)-Catalyzed Click Chemistry in Glycoscience and Their Diverse Applications
• Efficient chemoenzymatic synthesis of biotinylated human serum albumin-sialoglycoside conjugates containing O-acetylated sialic acids. [europepmc]
• Click chemistry in peptide-based drug design. [europepmc]
• Isocyanide-based multicomponent reactions towards cyclic constrained peptidomimetics. [europepmc]
• Drude Polarizable Force Field Parametrization of Carboxylate and N -Acetyl Amine Carbohydrate Derivatives. [europepmc]
• Synthesis of C -linked α-Gal and α-GalNAc-1'-hydroxyalkanes by way of C2 functionality transfer. [europepmc]
• Extending the in vivo persistence of synthetic glycoconjugates using a serum-protein binder. [europepmc]

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