CAS: 1065008-97-0—The core building block of glycoprotein engineering and glycosylation research

2-methyl-polymannosyl oxazole (GlycanOxazoline) is a key derivative molecule in the fields of glycochemistry and glycobiology. As an efficient glycosylation tool, it is known as a revolutionary building block for glycoprotein synthesis and modification. It is not only an important intermediate in the construction of complex glycoconjugates, but also an indispensable core raw material for modern biomedicine, especially the development of therapeutic glycoproteins, enzymatic glycosylation engineering, and research on sugar-related diseases. Its unique structure gives it high efficiency and specificity in enzymatic reactions, providing a powerful platform for the precise introduction of uniform sugar chains and promoting progress from basic science to innovative therapies.

Chemical Information

Chemical name: 2-methyl-[α-D-mannopyranosyl-(1->3)-[α-D-mannopyranosyl-(1->6)]-α-D-mannopyranosyl-(1->6)-[α-D -mannopyranosyl-(1->3)]-β-D-glucopyranosyl-(1->4)-1,2-dideoxy-α-D-glucopyrano]-[2,1-d]oxazoline

Common name: Glycan Oxazoline derivatives

Chemical formula: C38H63NO30

Molecular weight: 1013.90 g/mol

CAS number: 1065008-97-0

Structural features

This compound belongs to the Glycan Oxazoline category. Its structure is complex and exquisite, and it has the following outstanding characteristics:

Oxazoline core: The molecule contains a [2,1-d]oxazoline ring, which is derived from the 1,2-dideoxy-α-D-glucopyrano moiety. As a glycosyl donor, this oxygen-nitrogen heterocyclic structure is highly reactive in enzymatic reactions and can be efficiently transferred to acceptors (such as proteins or peptide chains) through glycosyltransferases to form stable glycosidic bonds. Compared with traditional glycosylation methods, this design avoids the need for active group protection and simplifies the synthesis process.

Multi-branched mannose chain: The structure contains four α-D-mannopyranosyl units connected by specific α-(1->3) and α-(1->6) glycosidic bonds to form a highly branched oligosaccharide chain. This arrangement simulates the common high-mannose N-glycan structure in natural glycoproteins (such as Man4GlcNAc analogs), providing an accurate chemical model for studying the biological functions of sugar chains.

Enhanced stability and specificity: The C-N bond of the oxygen nitrogen heterocycle gives the molecule chemical stability under mild enzymatic conditions and reduces side reactions. At the same time, the three-dimensional configuration of the branched mannose chain (α-linked) ensures precise recognition with glycosyltransferases (such as endoglycosidase ENGase) to achieve site-specific glycosylation, thereby maintaining high fidelity in complex assembly.

Flexible glycosylation site: connected to the oxynitrogen heterocycle core through β-D-glucopyranyl-(1->4), this molecule can be used as a modular building block to further expand the complexity of the sugar chain or couple with other biomolecules, and is suitable for diversified sugar engineering strategies.

Main applications and advantages

Core tools for therapeutic glycoprotein production

In biopharmaceuticals, glycosylation modifications significantly affect protein stability, immunogenicity, and pharmacokinetics. This Glycan Oxazoline derivative serves as a high-quality substrate for enzymatic glycosylation and can be used to reconstruct or modify the sugar chains of therapeutic antibodies, enzymes and hormones. Through the endoglycosidase-mediated transglycosylation reaction, uniform high-mannose chains can be directly introduced into specific protein sites, overcoming the limitations of glycosylation heterogeneity in traditional cell expression systems and improving drug batch consistency and efficacy. For example, in cancer immunotherapy, optimizing the glycans in the Fc region of an antibody can enhance effector function, and this molecule provides a chemically precise solution for this.

Advanced probes for glycobiology and enzymology research

As a well-defined oligosaccharide oxynitrogen heterocycle, this compound is an ideal tool for exploring glycosyltransferase mechanisms, sugar-protein interactions, and sugar chain metabolic pathways. Its branched mannose structure can be used to study lectin recognition, pathogen-host interactions (such as viral glycoprotein binding to immune cells), and endoplasmic reticulum-related degradation processes. In enzymatic screening, it helps identify new glycoengineering enzymes and promotes customized design of sugar chains in synthetic biology.

Platform for diagnosis and drug development of sugar-related diseases

Aberrant glycosylation is closely associated with a variety of diseases such as cancer, neurodegenerative diseases, and immune disorders. Glycoconjugates derived from this molecule can be used as standards or probes for the development of diagnostic methods based on glycoprofiling, such as liquid chromatography-mass spectrometry detection or microarray technology. In addition, in vaccine development, glycoantigen mimics can induce specific immune responses, and this oxonitrogen heterocyclic building block can be used to synthesize sugar vaccine candidate molecules, providing new strategies for targeting fungal or bacterial infections.

Innovative building blocks of synthetic chemistry and materials science

In chemical synthesis, the stability of this compound allows it to be used as a key intermediate in multi-step reactions for the construction of complex sugar polymers, dendrimers or functionalized nanomaterials. The polyhydroxyl properties of its sugar chains can also be derived into biocompatible coatings, which can be used in drug delivery systems or tissue engineering scaffolds to enhance targeting and biological functions.

Conclusion

2-methyl-polymannosyl oxynitrogen heterocycle is not only a chemical entity, but also a bridge between glycoscience and therapeutic applications. From decoding the glycosylation code to designing next-generation biologics, its value is increasingly evident in basic research and translational medicine. As glycoengineering technology evolves, this molecule will continue to empower precision medicine and open up new paths for infectious disease prevention and control, cancer treatment and regenerative medicine.

The above information is provided by the editor of KASONS and is for scientific research only.