Mannoseserine—advanced building block for glycosylation research and glycopeptide drug development 118358-80-8

Today, with the rapid development of glycobiology and glycodrug research and development, precise control of protein glycosylation modification has become the key to understanding life processes and developing new therapies. Mannoseserine (Tetra-O-acetyl-α-Mannosyl-Fmocserine, CAS No. 118358-80-8), as a type of glycosylated amino acid building block with clear structure and excellent reaction characteristics, is providing an indispensable chemical tool for this frontier field.

Chemical Information

Chemical name: Tetra-O-acetyl-α-Mannosyl-Fmocserine

Common name: Mannoseserine (Fmoc protected)

Chemical formula: C₃₂H₃₅NO₁₄

Molecular weight: 657.62 g/mol

CAS number: 118358-80-8

Category: Glycopeptides

Structural features

The design of this molecule elegantly combines the needs of glycochemistry with peptide synthesis chemistry:

Clear glycosyl linkage: Mannose is specifically linked to the hydroxyl group of the serine side chain through an α-glycosidic bond, providing a precise starting point for constructing a specific configuration of O-linked glycosylation structures.

Dual protection strategy: All hydroxyl groups on the mannose ring are protected by acetyl groups (Ac), ensuring the stability of the sugar moiety under the acidic conditions of subsequent solid-phase peptide synthesis (SPPS) and preventing unnecessary side reactions. The α-amino group of serine is protected by fluorenylmethoxycarbonyl (Fmoc), which can be removed under mild alkali treatment conditions and is fully compatible with the standard Fmoc solid-phase peptide synthesis process.

Excellent synthetic applicability: This combination of protecting groups enables the building block to be directly used in an automated peptide synthesizer to efficiently and sequentially introduce glycosylated amino acids into designated positions of the target peptide chain. It is an ideal building block for controllable synthesis of complex glycopeptides.

Main applications and value

Chemical synthesis of glycopeptides and glycoproteins

It is the core raw material for the preparation of structurally uniform and well-defined O-linked glycopeptides through solid-phase synthesis. Researchers can use it to precisely introduce mannosylation modifications at specific sites in the peptide chain for the preparation of standards, probes or bioactive glycopeptide drug candidates for scientific research.

Study on the function and mechanism of glycosylation

Protein glycosylation, especially O-linked glycosylation, profoundly affects protein folding, stability, cellular localization, immunogenicity and biological activity. Model glycopeptides synthesized using such structurally precise building blocks are valuable tools for elucidating how specific glycoforms (e.g., mannosylation) affect protein function and the molecular mechanisms underlying its interaction with receptors such as lectins.

Carbohydrate drugs and vaccine development

In the design of new vaccines (especially vaccines based on antigenic peptides) and carbohydrate-targeted drugs, the glycosylation pattern of the antigenic peptide is an important means to regulate its immunogenicity, targeting and stability. It provides a direct chemical synthesis solution for the rational design and optimization of such glycosylated antigen peptides or therapeutic glycopeptides.

Basic tools of glycobiology

As a high-quality standardized reagent, it greatly facilitates research in the fields of glycobiochemistry and chemical biology, helps explore the role of glycosylation in the occurrence and development of diseases (such as cancer, immune diseases, infectious diseases), and promotes the discovery of relevant diagnostic biomarkers.

Conclusion

Tetra-O-acetyl-α-Mannosyl-Fmocserine is much more than a chemical molecule. It represents a sophisticated interface at the intersection of synthetic chemistry and life sciences, and is an important key to decoding the biological language of glycosylation and ultimately translating it into innovative therapies. From basic scientific research to application development, it provides researchers who are committed to the forefront of glycoscience with powerful capabilities to achieve precise design and synthesis, helping to unlock the unlimited potential of the glycopeptide world.

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