CAS: 1065008-98-1—Key glycosyl oxazolines in glycoscience and glycoengineering research

α-Man-(1->3)-β-Glcp-(1->4)-GlcpNAc is an oligosaccharide oxazoline derivative with a clear structure and a specific connection method. As an important member of the Glycan Oxazoline family, this compound shows unique value in the fields of basic glycobiology research and glycoprotein engineering applications. It is a core chemical entity for exploring glycosylation mechanisms and developing enzymatic synthesis tools.

Chemical Information

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

Common name: Trisaccharide oxazoline (Man-Glc-GlcNAc Oxazoline)

Chemical formula: C20H33NO15

Molecular weight: 527.48 g/mol

CAS number: 1065008-98-1

Structural features

This molecule is an oxazoline derivative with a trisaccharide structure. Its core characteristics are:

Oxazoline ring structure: On the N-acetylglucosamine (GlcNAc) unit at the reducing end, a 1,2-oxazoline ring is formed. This ring structure mimics the transition state or oxonium ion intermediate in the glycosyltransferase catalyzed reaction, making it an efficient substrate or inhibitor for endoglycosyltransferases/glycosyltransferases.

Precise glycosidic linkage: The sequence contains α-(1->3)-linked mannose (Man) and β-(1->4)-linked glucose (Glc), which are then connected to oxazoline-cyclized GlcNAc through β-(1->4) bonds. This specific connection pattern corresponds to the N-glycan core or branch structure of many natural glycoproteins and is of high biological relevance.

Balance of reactivity and stability: The introduction of the oxazoline ring gives the molecule specific reactivity, especially in enzymatic glycosylation. It can be efficiently recognized by certain glycosidases (such as Endo-M, Endo-A, etc.) and used for sugar chain transfer. At the same time, its chemical stability is better than that of directly activated glycosyl donors, making it easier to store and operate.

Main applications and value

Key substrate for enzymatic glycoprotein synthesis and remodeling

In the technology of chemoenzymatic synthesis of uniform glycoproteins, this type of oligosaccharide oxazoline is the core "glycosyl donor". It can be utilized by endo-β-N-acetylglucosaminidase (ENGase) enzymes to efficiently and specifically transfer the entire oligosaccharide chain to the specific glycosylation site (such as GlcNAc-asparagine) of the target protein or peptide chain through a transglycosylation reaction, thereby achieving the synthesis of complex glycoproteins or the precise reshaping of existing glycoprotein sugar chains.

Tool molecules for glycosyltransferase mechanism research and inhibitor development

Since its structure mimics the catalytic transition state of enzymes, this compound is a valuable probe for studying the mechanism of action of related endoglycosidases and glycosyltransferases. It can be used for enzyme active site analysis and kinetic studies, and can be used as a lead structure for the design of efficient and specific enzyme inhibitors, providing a chemical basis for the development of treatment strategies for glycosylation-related diseases.

Universal building blocks for the synthesis of complex oligosaccharides and glycoconjugates

As an oligosaccharide oxazoline with a well-defined structure, it is an excellent starting module or intermediate for the top-down synthesis of more complex, longer-chain oligosaccharides or polysaccharides. Through enzymatic or chemical means, the sugar chain can be further extended to construct a precise sugar structure with biological significance, which can be used to prepare sugar chips, vaccine candidates (such as vaccines based on sugar antigens), or as molecular probes to study sugar-protein interactions.

Standardized reagents for glycobiology and glycomics research

When analyzing glycoprotein structure, identifying sugar-binding proteins, or studying sugar-mediated biorecognition processes, this highly pure, structurally defined oligosaccharide oxazoline can serve as an important reference standard or competitive ligand to help resolve the precise relationship between a specific sugar chain structure and its biological function.

Conclusion

α-Man-(1->3)-β-Glcp-(1->4)-GlcpNAc As a type of Glycan Oxazoline with distinctive characteristics, it transcends the role of ordinary oligosaccharides and is an active bridge molecule connecting glycochemistry and glycobiology. It constitutes an indispensable research tool and innovation cornerstone in promoting precise glycoprotein synthesis, analyzing the mechanism of glycosylation enzymes, and developing new technologies targeting sugar, and continues to contribute to breakthroughs and development in the cutting-edge field of glycoscience.

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