Application of Ugi Reaction and Polysaccharide Conjugation

The Ugi reaction is a multi-component reaction that allows the synthesis of a range of molecules in a single reaction. It achieves the synthesis of diverse compounds by introducing several different chemicals in a single reaction. The reaction was invented by German chemist Ivar Karl Ugi in 1959. This reaction usually involves an acid catalyst, an acyl reagent, an amine, and a tertiary amine or an imine. These components would form a multi-component system, and complete the reaction. In polysaccharide conjugation, the Ugi reaction can be used to introduce a variety of functional groups, resulting in a difference in the structure of polysaccharide conjugates or changing the properties and functions of the polysaccharide. In polysaccharide conjugation, polysaccharides may play the role of amines and also act as carriers for acid catalysts. This approach improves polysaccharide stability, water solubility, and bioactivity. In addition, it improves biological activity and provides a valuable tool for glycol-drug research.

Ugi Reaction-based Polysaccharide Conjugation Services at CD BioGlyco

CD BioGlyco offers polysaccharide conjugation service based on the Ugi reaction, which enables the conjugation of different functional groups by organic reactions of multiple functional groups, thereby introducing diverse functional groups on polysaccharide molecules. The specific services we offer include the following:

• We introduce monomers containing Ugi-reactive functional groups on polysaccharide molecules and then perform the conjugation of polysaccharides and other reactants under Ugi reaction conditions. The produces polysaccharide conjugate with high product purity and fewer side reactions
• A variety of monomers containing Ugi-reactive functional groups react with polysaccharides under Ugi-reactive conditions to produce a variety of additional products. For example, monomers containing different Ugi-reactive functional groups can be reacted with polysaccharides in the Ugi reaction to obtain a plurality of products.
• We introduce Ugi reaction precursors on polysaccharide molecules, which are then subjected to the Ugi reaction conditions for conjugation with other reactants. With higher structural diversity, various types of polysaccharide conjugates can be synthesized by selecting different reaction precursors.

Fig.1 The flowchart of Ugi reaction-based polysaccharide conjugation. (CD BioGlyco)

Applications

• Research on cell signaling
• Preparation of polysaccharide-based vaccines
• Research related to the chemical analysis of glycans

Advantages of Us

• Great applicability
• Mild reaction conditions
• First-class service

CD BioGlyco has established a state-of-the-art Glyco™ Vaccine Development Platform, providing clients with Ugi reaction-based Polysaccharide Conjugation service. We perform efficient reactions to selectively conjugate multiple functional groups according to your needs and customize your target compounds using a wide range of polysaccharide molecules. If you have a demand in this field, please contact us and we will be delighted to provide you with the best service.

Reference:

1. Reguera, L.; et al. Multicomponent reactions in ligation and bioconjugation chemistry. Accounts of Chemical Research. 2018, 51(6): 1475-1486.