Fucosyl lactone-N-hexose-high purity standard for glycobiology research 116883-09-1

At the intersection of glycoscience and biopharmaceuticals, glycosylation modification, as one of the most important post-translational modifications, directly regulates the structure, function, stability and immunogenicity of proteins. Among them, fucosylation plays a central role in cell recognition, signal transduction, inflammatory response and cancer progression. The star compound in the field of glycobiology research, fucosylactone-N-hexose (TFLNH), is an indispensable high-quality chemical tool for decoding the sugar code of life and empowering the next generation of biological therapies.

Chemical Information

Chemical name: Fucosyl lactone-N-hexose

Common name/abbreviation: TFLNH[A]

Chemical formula: C₅₈H₉₈N₂O₄₃

Molecular weight: 1511.39 g/mol

CAS number: 116883-09-1

Structural Characteristics and Biological Relevance

TFLNH is a complex oligosaccharide or glycoconjugate derivative with clear structure and high purity. Its structural characteristics make it an ideal model and tool for glycobiology research:

Core fucosyl unit: The molecule contains a fucose group, which is a common 6-deoxyhexose sugar. Fucosylation, especially core fucosylation (linked to the innermost GlcNAc of the N-linked sugar chain), is a key factor in regulating antibody-dependent cell-mediated cytotoxicity (ADCC) effects. Defucosylated IgG1 antibodies have shown significantly enhanced ADCC activity and have become a hot topic in the optimization of anti-cancer antibody drugs.

Lactone structural characteristics: The "lactone" part indicates that there may be a cyclic ester structure formed by sugar acid in the molecule. This structure is unique in glycochemistry and can be used as a chiral precursor or active intermediate in chemical reactions for further chemical modification or coupling, providing an entry point for the synthesis of customized sugar probes or sugar materials.

N-hexose backbone: It is suggested that the molecule contains derivatives or analogs of an N-linked glycan core structure (such as pentasaccharide core: Man₃GlcNAc₂) linked to asparagine (Asn). This makes it directly related to the quality properties of glycoproteins and is a direct molecular template for studying intracellular glycosylation pathways, glycoprotein folding and quality control, and cell surface receptor-ligand interactions.

Main applications and core advantages

1. The “gold standard” for glycoprotein drug development and quality control analysis

Biosimilar and biomodified drug development: In the development of therapeutic antibodies (such as monoclonal antibodies) and fusion proteins, glycosylation profiles are a critical critical quality attribute (CQA). TFLNH can be used as a standard or reference material for:

Chromatographic analysis: In HPLC (such as HILIC) or CE analysis, it is used for qualitative and quantitative detection of specific fucosylated glycoforms in the complex oligosaccharide mixture released after glycoprotease cleavage.

Mass spectrometry analysis: As an accurate standard with known molecular weight, it is used for calibration and glycoform identification of LC-MS or MALDI-TOF MS to ensure the accuracy and reliability of analysis results.

Process optimization: By monitoring the glycoform changes (such as fucosylation level) produced during the cell culture process, we guide the optimization of the upstream cell culture process and downstream purification process to obtain the glycoform distribution with ideal therapeutic effects.

2. Cutting-edge disease mechanism research and biomarker discovery

Cancer Research: Aberrant fucosylation has been confirmed to be a prominent feature of various malignancies (such as liver cancer, pancreatic cancer, colorectal cancer). TFLNH can be used for:

Inhibition research: As a starting point for research on potential substrate analogs or inhibitors of fucosyltransferases (FUTs, such as FUT8), explore new strategies to intervene in tumor growth and metastasis by regulating fucosylation.

Probe development: Labeling cells or tissues after derivatization, used to track the spatiotemporal changes of abnormal fucosylation in the occurrence and development of diseases, and help discover new disease-related sugar biomarkers.

Immune and Inflammatory Diseases: Fucosylation is critical in leukocyte homing (via selectin ligands), immune regulation. TFLNH can be used to study the role of related glycosylation events in pathological processes such as autoimmune diseases and allergic reactions.

3. Core tools for enzymology research and diagnostic tool development

Glycosyltransferase/Glycosidase Activity Assay: Used as a highly specific substrate for determining the activity of fucosyltransferases or glycosidases that break down specific fucosidic bonds, for enzyme functional characterization, inhibitor screening, or development of clinical enzyme activity detection kits.

Affinity reagent and vaccine design: The unique fucosylation structure can be specifically recognized by certain lectins (such as AAL, LCA) or antibodies. TFLNH can be used to prepare affinity chromatography media for the separation and purification of glycoproteins; or as a hapten to develop diagnostic antibodies that detect specific sugar structures. It also has potential value in the design of carbohydrate-based antibacterial/anticancer vaccines.

4. A powerful tool for basic glycobiology research

Structure-function relationship research: Provides a molecular entity with a clear structure for studying how specific fucosylation patterns affect the three-dimensional conformation, stability, half-life and interaction with other biological macromolecules of glycoproteins.

Cell signaling research: used to explore the mechanism of fucosylation modification in the functional regulation of membrane proteins such as growth factor receptors and integrins.

Conclusion

Fucosylactone-N-hexose (TFLNH) is more than just a compound, it is a bridge between basic research in glycochemistry and cutting-edge applications in biomedicine. From in-depth understanding of the nature of diseases to precise regulation of biological efficacy to the development of innovative diagnostic tools, TFLNH, as a key standard and tool molecule, is helping scientists around the world to continuously make breakthroughs in the field of glycoscience.

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