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GlycoCLICK™-based Chemical Synthesis Service

GlycoCLICK™-based Chemical Synthesis Service at CD BioGlyco

Click reaction is a commonly used chemical reaction technique that is applied to the synthesis and modification of sugars. This technology is based on the high selectivity of substrates and the rapidity of the reaction, which introduces various functional groups on sugar molecules. CD BioGlyco has strong technical teams that synthesize various sugar compounds via GlycoCLICK™ technology, such as oligosaccharides, glycopeptides, sugar clusters, and glycosides. We introduce different functional groups to tailor the properties and applications of sugar molecules by using this technology.

Synthetic route design service

We determine the structure and specification requirements of the compounds to be synthesized according to the client's needs. We design the synthesis route as required and determine the required starting materials and intermediates.

Starting material preparation service

According to the designed synthetic route, we introduce the required functional groups into the starting materials, which are usually relatively simple sugar-based structures, such as glucose or galactose.

Click reaction-based synthesis service

We use GlycoCLICK™ technology to perform a click reaction between the starting material and the corresponding click reagent (such as an alkyne or azide compound) to form a connection of sugar chains or sugar clusters. We apply various types of click reactions to synthesize sugar compounds.

Copper-catalyzed azide-alkyne cycloaddition (CuAAC): It is one of the most commonly used click reaction types and is used to connect molecules containing azido groups in sugars with molecules containing alkynyl groups in sugars. This reaction requires the presence of a copper catalyst and is carried out under alkaline conditions.
trans-Cyclooctene (TCO)-TCO reaction: TCO is a click reaction group containing a cyclopropenyl group, which undergoes rapid cycloaddition reactions with other molecules containing TCO groups, which is used for click synthesis and labeling of sugars.
Tetrazine-trans-cyclooctene (Tz-TCO) reaction: Efficient click ligation is achieved by reacting molecules containing tetrazine and TCO groups.

These click reaction types are characterized by rapidity, high selectivity, and high yield, and are widely used in glycochemistry. We provide many types of GlycoCLICK™-based chemical synthesis services, including but not limited to the following.

GlycoCLICK™-based Oligosaccharide Synthesis

CD BioGlyco uses various types of click chemical reaction strategies to synthesize diverse oligosaccharides, such as C-disaccharide, S-disaccharide, and O-disaccharide.

GlycoCLICK™-based Glycopolymer Synthesis

Carbohydrate-containing synthetic polymers are a popular class of biomaterials. CD BioGlyco uses click chemistry technology to insert carbohydrate molecules into the polymer backbone to form glycopolymers or block copolymers.

GlycoCLICK™-based Glycolipid Synthesis

GlycoCLICK™ is an innovative click chemistry technology. CD BioGlyco uses it to efficiently connect sugar groups with fatty acids or other lipid molecules to form glycolipid compounds.

GlycoCLICK™-based Glycopeptide Synthesis

CD BioGlyco offers professional GlycoCLICK™-based glycopeptide synthesis service, we customize the synthesis of peptide compounds with specific glycosyl groups for clients, which is of great significance to glycobiology in the research and application fields.

GlycoCLICK™-based Glycoside Synthesis

GlycoCLICK™ technology provides diversity and flexibility in synthesis strategies. CD BioGlyco offers various types of glycoside synthesis services and we select different sugar groups and substrate molecules to obtain the desired glycoside structure. For example, we synthesize glycosides with triazole bridges through click chemistry. Triazole glycosides and their derivatives usually have antibacterial, anti-inflammatory, and antiviral activities.

GlycoCLICK™-based Glycocluster Synthesis

Glycoclusters are a unique structure formed by multiple sugar molecules linked through chemical bonds, which has important applications in biomedical research and drug development. We provide mature GlycoCLICK™-based synthesis for multiple types of glycoclusters, such as C-Glycan Cluster, S-Glycan Cluster, O-Glycan Cluster, and Heteropolysaccharide Cluster Synthesis Service.

GlycoCLICK-based Glycodendrimer Synthesis

Glycodendrimers have multiple branches and hierarchical structures that mimic the complex structure of natural glycolipids or glycoproteins. We customize combinations of different branches and sugar groups to synthesize the desired glycodendrimer structure.

GlycoCLICK™-based Macrocycle Synthesis

GlycoCLICK™ is a novel glycosyl chemistry-based technology that has unique advantages in macrocycle synthesis. CD BioGlyco connects the functional groups of sugars to other molecules through simple and efficient click reactions to synthesize various complex macrocyclic compounds, such as Unnatural Heparin and Chondroitin.

GlycoCLICK™-based Multivalent Glycoconjugate Synthesis

Multivalent glyconjugates have broad application prospects in the fields of vaccine development, drug delivery systems, cell recognition, and immune regulation. We provide an efficient synthesis of various types of GlycoCLICK™-based multivalent glycoconjugate synthesis services. For example, Mannosylated Ligand, Sugar Heterodimer, Calix-sugar, and Glycocyclodextrin Synthesis services.

GlycoCLICK™-based Glycoprotein Synthesis

Glycoproteins have wide application value in biology and drug development. CD BioGlyco provides high-quality GlycoCLICK™-based glycoprotein synthesis service to meet clients' needs for glycoproteins, thereby helping them carry out research work.

Extension chain synthesis service

After the click reaction, we continue to expand the sugar chain to increase the number of sugar units according to client needs, which is accomplished by introducing new click reagents into the click reaction or by other synthetic methods.

Separation and purification service

We use techniques such as column chromatography, gel filtration, or reversed-phase high-performance liquid chromatography (HPLC) to separate and purify the synthesized products. Impurities are removed through the purification process to obtain high-purity target products.

Characterization and analysis service

We conduct structural characterization and analysis of the synthesized products, and use various analytical techniques, such as mass spectrometry, nuclear magnetic resonance, infrared spectroscopy, etc., to verify the structure and purity of the products.

Large-scale synthesis service

We also provide various types of large-scale GlycoCLICK™-based chemical synthesis services. At the same time, we provide custom synthesis services according to specific synthesis goals.

Fig.1 GlycoCLICK™-based chemical synthesis service. (CD BioGlyco)

Publication

Technology: Cu(I)-catalyzed click dipolar cycloaddition reaction

Journal: Journal of Enzyme Inhibition and Medicinal Chemistry

IF: 5.756

Published: 2021

Results: The authors synthesized a series of molecular hybrids of thienopyrimidine-linked triazole glycosides via a Cu(I)-catalyzed click dipolar cycloaddition reaction and studied their cytotoxicity against two cancer cell lines in vitro. The results showed that triazole glycosides 16 and 18 had significant cytotoxic activity against the HCT-116 cell line, while all studied derivatives showed excellent activity against the MCF-7 cell line, which may provide a promising template for the anti-cancer field.

Fig.2 Synthesis of triazole glycosides. (Khattab, et al., 2021)

Applications

Drug R&D: Sugar molecules play a key role in many biological processes, such as cell recognition, signal transduction, etc. GlycoCLICK™-based chemical synthesis service is applied to synthesize sugar molecule derivatives for drug development and screening, including agonists or inhibitors of sugar receptors.
Vaccine research: Sugar molecules are an important part of the surface of many pathogens. The use of click technology to synthesize sugar molecules will help research and develop vaccines against specific pathogens, thereby enhancing the immune system's defense against pathogens.
Biomaterials: The use of click technology to synthesize sugar chain derivatives will help develop functional materials for the field of biomaterials, such as biomimetic surface coatings, tissue engineering scaffolds, etc., to achieve better cell compatibility and bioactivity.

Advantages

Efficient process development: CD BioGlyco quickly develops reliable process routes suitable for different sugar structures and continuously improves synthesis efficiency.
Advanced technical means: CD BioGlyco uses the latest click chemistry technology to achieve high selectivity and high yield of sugar molecule synthesis. At the same time, we use advanced analytical technology to conduct comprehensive analysis and characterization of synthetic products.
Flexible production scale: We provide small-scale or large-scale GlycoCLICK™-based chemical synthesis services according to client needs.

CD BioGlyco has in-depth knowledge and experience in the field of glycochemistry. We use mature GlycoCLICK™-based chemical synthesis technology to synthesize various types of sugar molecules. At the same time, we provide a one-stop comprehensive service from synthesis design, synthesis preparation, and purification to analysis and verification. In addition, we also provide GlycoCLICK™-based Modification Service and Labeling Service. Please feel free to contact us if you are interested in our GlycoCLICK™-based synthesis services, and we look forward to cooperating with you.

Reference

Khattab, R.R.; et al. Click chemistry based synthesis, cytotoxic activity and molecular docking of novel triazole-thienopyrimidine hybrid glycosides targeting EGFR. Journal of Enzyme Inhibition and Medicinal Chemistry. 2021, 36(1): 504-516.

For research use only. Not intended for any clinical use.

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