Calix-sugar Synthesis Service
Wholeheartedly Dedicated Calix-sugar Synthesis Service for Clients
CD BioGlyco is skilled in the use of click chemistry to synthesize Multivalent Glycoconjugates with specific affinities, including calix-sugar, Mannosylated Ligand, etc. Multivalent glycoconjugates such as calix-sugar have good functionality and are used to study various carbohydrate events. We offer a custom synthesis service of calix-sugar to support our clients' research in this area.
- Synthesis of calix-sugars
We synthesize calix-sugars by introducing carbohydrate portions mainly at the upper or lower edges of calixarenes. Commonly used scaffolds include calix[4]arene and calix[8]arene. We proceed by utilizing different carbon-carbon and carbon-heteroatom bonding reactions to attach the carbohydrate units to the calixarene scaffolds through various tethered chains. There are various types of synthesis methods. We select the appropriate method for the synthesis according to the client's requirements. After synthesis, we analyze the structure of the compounds by electrospray ionization (ESI) mass spectrometry, proton nuclear magnetic resonance (1H NMR), and carbon-13 nuclear magnetic resonance (13C NMR).
- Synthesis methods
In studies of the construction of multivalent structures such as calix-sugars, sugar heterodimer, glycocyclodextrin, etc., it is found that 1,3-dipolar cycloaddition is a very effective tool. This method permits the simultaneous construction of aromatic systems, thus facilitating the formation of aromatic systems. Among them, copper(I)-catalyzed 1,3-dipolar cycloaddition between terminal alkynes and organic azides (CuAAC) is a commonly used strategy. We mainly employ CuAAC to synthesize various calix-sugars. In addition to this, we also synthesize calix-sugars by the following methods.
- Palladium-catalyzed coupling
- Nucleophilic substitution in tosyltetrazoles
- Glycosylation
- S-alkylation
- Mide bond formation
- Thiol–ene coupling
- Mitsunobu reaction
- Wittig olefination
- Isothiocyanate–amine addition
Publication Data
Technology: CuAAC
Journal: The Journal of Organic Chemistry
IF: 4.335
Published: 2008
Results: In the present study, the CuAAC click tool was used to glycosylate calix[4]arene for the synthesis of structurally well-defined calix-sugars. They coupled tetra-azidopropyl-calix[4]arene 2 with ethynyl tetra-O-benzyl-C-galactoside 1a. A triazole-linked tetra-C-galactosyl-calix[4]arene was finally synthesized. Solubility of the reagents, extraction of the product, etc., were explored during the study, and ultimately the reaction was found to be very high yielding up to 90%.
![Fig.1 Synthesis of defined calix-sugar by incorporation of sugar on calix[4]arene.](https://glycoclick.bioglyco.com/wp-content/themes/glycoclick/img/1-1-9-3-calix-sugar-synthesis-service-2.jpg)
Fig.1 Synthesis of structurally defined calix-sugar using CuAAC. (Vecchi, et al., 2008)
Applications
- Based on its chiral and polyhydroxylated nature, calix-sugar represents a promising class of molecular receptors that are used to study physiological processes such as cell signaling.
- Synthesized structurally different calix-sugar are used in molecular recognition studies, mainly for plant lectins, among others.
- Synthesis of highly functionalized calix-sugar plays an important role in drug development and synthesis.
Highlights of Us
- We synthesize structurally complex calix-sugar by incorporating various sugars on calix[4]arene and calix[8]arene.
- The chemistry of our synthesis of calix-sugar is carried out under mild conditions in high yields with good stereoselectivity.
- We synthesize various calix-sugar with the help of advanced modeling and cheminformatics software.
CD BioGlyco has deep scientific knowledge and extensive experience in click chemistry. We bring deeper and more sophisticated expertise and high-quality products to our clients. Please feel free to for more information about calix-sugar synthesis. We will surely provide you with comprehensive and high-quality calix-sugar synthesis services.
References
- Dondoni, A.; Marra, A. Glycopolymer code: Synthesis of glycopolymers and their applications. The Royal Society of Chemistry. 2015: 96-148.
- Vecchi, A.; et al. Microwave-enhanced ionothermal CuAAC for the synthesis of glycoclusters on a calix [4] arene platform. The Journal of Organic Chemistry. 2008, 73(16): 6437-6440.
