C-Glycan Cluster Synthesis Service
Efficient Click Chemistry Techniques for C-Glycan Cluster Synthesis at CD BioGlyco
Click Chemistry is a method widely used in organic synthesis. CD BioGlyco uses click chemistry technology to provide mature Glycocluster Synthesis services. We use diversified click technologies to efficiently introduce C-bonds to sugar groups to synthesize C-sugar clusters. Constructing C-glycan clusters with specific structures and functions study their interactions with biological molecules (such as proteins, and cell surface receptors), thereby revealing the mechanisms of biological processes and signal transduction. Our synthesis process includes but is not limited to the following.
- Synthesis design and customization: Based on client needs, we provide C-glycan cluster synthesis design and customization service. We determine the structure of the C-glycan cluster that needs to be synthesized, analyze the glycosyl units, and design a suitable synthesis route according to the required structure and functions.
- Synthesis of starting materials: We synthesize starting materials through appropriate organic synthesis steps and conditions. The starting materials are usually sugar molecules containing protective groups, such as glycosides containing protected hydroxyl groups.
- Introduction of alkynylated sugar molecules: We couple the synthetic starting materials with alkynylated sugar molecules to generate C-alkynylated sugar molecules. This reaction usually uses a palladium complex as a catalyst and the coupling is performed under alkaline conditions.
- Click coupling: We click-react the synthesized sugar molecule with a substrate bearing an activating group, such as an azide. This reaction is called azide-alkyne cycloaddition and is usually promoted using a copper catalyst and auxiliary ligands such as triphenylphosphine. Click reactions are highly specific and perform selective bonding in complex molecular environments. It targets the reaction between the C-alkynyl group on the sugar moiety and the activated group (such as azide) to avoid non-specific reactions with other biological macromolecules or complex mixtures.
- Repeated click coupling: We select different glycosyl units for repeated click coupling to gradually synthesize the C-glycan cluster.
- Deprotection: After the synthesis of the C-glycan cluster is completed, we use appropriate conditions to remove the protecting group.
- Purification and characterization: Finally, we purify and characterize the synthesized C-glycan cluster to ensure that a high-quality and high-purity target C-glycan cluster is obtained. In addition, we also perform activity evaluation of the C-glycan cluster to help clients understand its functions and potential applications.
Publication
Technology: Cu(I)-catalyzed azide-alkyne cycloaddition reaction
Journal: New Journal of Chemistry
IF: 3.925
Published: 2016
Results: The authors selected C60-fullerene and β-cyclodextrin as core molecules, and synthesized multivalent C-glycosides through a Cu(I)-catalyzed azide-alkyne cycloaddition reaction. The authors then designed these compounds as molecular probes to study the molecular mechanism of multivalent constructs inhibiting glycosidases. The results showed that the multivalent binding models based on the two structures achieved inhibitory effects, which can be used to design effective multivalent glycosidase inhibitors.
Fig.1 Schematic representation of monovalent and multivalent glycomimetics. (Stauffert, et al., 2016)
Applications
- Glycobiology research: C-glycan cluster is a type of glycosyl aggregate connected by C-glycosyl chemical bonds. Click chemistry technology is used to prepare C-glycan clusters with different sizes, topological structures, and glycosyl compositions to study their functions in glycoprotein interactions, cell signal transduction, and pathogen recognition.
- Vaccine development: C-glycan cluster is used to synthesize vaccine candidates that mimic the arrangement of C-glycosylated sugar groups on the surface of pathogens. These C-glycan clusters stimulate the immune system to produce specific antibodies and cellular immune responses, thereby protecting the body from infection.
- Drug discovery: Using click chemistry technology to synthesize drug compounds with different C-glycan clusters, their interactions with sugar receptors are evaluated to develop new drugs.
Advantages
- CD BioGlyco has advanced laboratory instrumentation and technology to support the complex C-glycan cluster synthesis process and analytical testing to ensure high-quality synthesis products.
- CD BioGlyco uses various analytical techniques to conduct structural verification and purity testing of the C-glycan cluster, such as nuclear magnetic resonance (NMR), mass spectrometry, etc. This ensures that the purity and structure of the synthetic products meet client requirements.
- CD BioGlyco provides different types of GlycoCLICK™-based glycan cluster synthesis services, such as C-glycan cluster, S-Glycan Cluster, O-Glycan Cluster, Heteropolysaccharide Cluster, to meet the diverse needs of clients.
The synthesis of the C-glycan cluster is a highly specialized process. CD BioGlyco has rich professional knowledge and technical capabilities in the fields of organic synthesis and glycochemistry. We provide high-level GlycoCLICK™-based C-glycan cluster synthesis services. Please feel free to contact us if you would like to inquire about specific content.
Reference
- Stauffert, F.; et al. Understanding multivalent effects in glycosidase inhibition using C-glycoside click clusters as molecular probes. New Journal of Chemistry. 2016, 40(9): 7421-7430.
For research use only. Not intended for any clinical use.
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