Hydrazone Ligation

The reaction of hydrazine or hydrazide-containing compounds with an aldehyde or ketone forms hydrazone bonds. Such bonds are a type of Schiff base. Compared to a standard Schiff base, they are less acid-labile. However, they are more labile than oxime bonds. In addition, the hydrazone bond formed from an aldehyde or a ketone impacts the degree of lability to acid. Also, hydrazone bonds formed from aromatic aldehydes are more stable than hydrazone bonds formed from aliphatic aldehydes.

Fig.1 Formation of hydrazone bonds. (Kale & Torchilin, 2023)

Hydrazone Ligation-based Cell Surface Chemical Conjugation Glycoengineering Service at CD BioGlyco

Hydrazone ligation is one of the important methods for the chemical conjugation of Cell Surface Glycoengineering. Scientists at CD BioGlyco have unique R&D expertise and rich experience in cell surface glycoengineering. To assist our client's specific objectives, we offer personalized according to the client's specific needs promptly.

• Conjugation of natural polysaccharides and synthetic carbohydrates
• Conjugation of glycan-protein
• Conjugation to nanoparticle carriers
• Labeling and modification of conjugates

Protein modification and labeling are common techniques for studying protein structure and interactions. Cross-linking is the process of chemically joining two or more molecules through covalent bonds. Modification involves attaching or cleaving chemical groups to change the solubility or other properties of the original molecule. Labeling generally refers to any form of cross-linking or modification whose purpose is to attach a chemical group (such as a fluorescent molecule) to aid detection.

• The purification of glycoconjugates

From conjugation to purification, we ensure the generation of high-quality conjugates, free of unincorporated labels.

• Glycoconjugates characterization
• Level of chemical derivatization; Colorimetric methods, mass spectrometry (MS), and Nuclear magnetic resonance spectroscopy (NMR spectroscopy).
• Check conjugate formation: Sodium dodecyl-sulfate polyacrylamide gel electrophoresis (SDS-PAGE), high-performance liquid chromatography (HPLC), MS.
• Quantify different saccharide types: Colorimetric methods, high-performance anion-exchange chromatography with pulsed amperometric detection (HPAEC-PAD), and gas chromatography-mass spectrometry (GC-MS).
• Determination of glycosylated sites of protein carriers: MS.
• Identification of polysaccharide structural integrity: By immunoassays or NMR spectroscopy.

Fig.2. Hydrazone ligation-based cell surface chemical conjugation glycoengineering. (CD BioGlyco)

Applications

• The applications of hydrazones include their biological activities, their utility as valuable synthetic intermediates, the multifunctionalization of biological scaffolds, and the preparation of protein conjugates.
• Hydrazone ligation reaction is employed in numerous scientific fields as a simple and versatile conjugation strategy, which is applied in fields as diverse as polymer chemistry, biomaterials and hydrogels, dynamic combinatorial chemistry, organic synthesis, and chemical biology.

Advantages

• Hydrazone ligation reaction preferably be stable across a broad range of biological environments and small in size to minimize its steric hindrance.
• Hydrazone ligation reactions proceed with high selectivity and specificity, moreover, the conjugation can be conducted in living systems without interfering with biological processes or metabolites.
• Hydrazone ligation reaction is a straightforward condensation, which is reversible and the conjugates can undergo hydrolysis in aqueous media.
• Our bioconjugation technology is engineered to allow rapid and quantifiable conjugation of all classes of biomolecules including antibodies, proteins, peptides, and oligonucleotides.

CD BioGlyco provides high-quality Cell Surface Chemical Conjugation Glycoengineering Services for clients and we have accumulated a lot of experience in Cell Surface Glycoengineering Technology. If you are interested in our services, please feel free to contact us.

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