CAS: 160067-63-0—Precision building blocks for glycopeptide synthesis and glycosylation studies

Today, with the rapid development of glycobiology and peptide drug research and development, precise control of glycosylation modification has become the key to improving protein stability and function. O-(2-Acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranosyl)-N-FMoc-L-serine, as a glycopeptide synthetic building block with high purity and clear structure, is providing an indispensable chemical tool for glycoprotein mimics, glycopeptide vaccines and glycosylation mechanism research.

Chemical Information

Chemical name: O-(2-acetylamino-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranosyl)-N-FMoc-L-serine

Common name: Acetyl protected GlcNAc-serine FMoc derivative

Chemical formula: C₃₂H₃₆N₂O₁₃

Molecular weight: 656.63 g/mol

CAS number: 160067-63-0

Category: Glycopeptides

Structural features

This molecular design integrates sophisticated strategies from the fields of glycochemistry and peptide synthesis:

Selective glycosylation site: The serine side chain hydroxyl group and fully acetylated GlcNAc (N-acetylglucosamine) are connected through a stable β-glycosidic bond, simulating the core structure of natural O-linked glycosylation modification.

Dual protecting group strategy:

Sugar ring protection: The 3, 4, and 6 hydroxyl groups are protected by acetyl groups to ensure that the sugar groups maintain structural integrity during subsequent peptide chain extension.

Amino protection: The α-amino group of serine is protected by FMoc (fluorenylmethoxycarbonyl), which is perfectly compatible with the solid-phase peptide synthesis (SPPS) process and can achieve automated and efficient assembly.

Modular design: The molecule has the dual functions of "glycosyl donor" and "amino acid derivative" and can be directly used in a peptide synthesizer to simplify the preparation process of complex glycopeptides.

Main applications and advantages

1. Key intermediates for glycopeptide and glycoprotein drugs

Biomimetic glycopeptide synthesis: Precisely construct O-GlcNAc-modified peptides to study the impact of glycosylation on protein folding, stability and activity, and to assist the development of related drugs for diabetes, neurodegenerative diseases and other diseases.

Glycopeptide vaccine development: The synthesis of tumor-associated carbohydrate antigens (such as Tn antigen) often relies on such building blocks to provide uniform and well-defined antigen fragments for the new generation of glycoconjugate vaccines.

2. Glycosylation mechanism and enzymology research tools

Glycosyltransferase substrate: As a starting template for enzymatic sugar chain extension, it is used to explore glycosyltransferase specificity and kinetic parameters.

Design of glycosidase inhibitors: The modified glycopeptide structure can simulate the enzyme substrate transition state, providing a basic framework for the development of inhibitors against pathogenic bacterial glycosidases.

3. Chemical synthesis process optimization

Efficient coupling: FMoc protecting group can be quickly removed under alkaline conditions, while acetyl sugar protecting group can be selectively removed after peptide chain synthesis, and is compatible with multi-step synthesis routes.

Conclusion

From decoding the biological code of glycosylation to developing next-generation glycosylation drugs, O-(2-Acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranosyl)-N-FMoc-L-serine represents a high degree of sophistication in the fusion of chemical synthesis and glycobiology. Whether you’re exploring the mysteries of sugar-protein interactions or building glycopeptide therapeutics with clinical potential, this molecule will become a trustworthy “smart building block” in your lab.

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