(Ac4GalNAl—core probe for metabolic labeling and imaging 1658458-26-4
N-(4-pentynoyl)-1,2,3,6-O-tetraacetyl-D-galactosamine (Ac4GalNAl) is a key metabolic probe reagent in the fields of glycobiology and chemical biology. As a chemically modified derivative of galactosamine, this compound achieves efficient and specific labeling and tracking of cellular metabolic pathways by integrating an alkynyl reporter group and an acetyl protecting group. Its design simulates natural sugar metabolic precursors, provides a powerful tool for studying glycosylation dynamics, cell surface engineering and disease mechanisms, and promotes progress from basic science to translational medicine.
N-(4-pentynoyl)-1,2,3,6-O-tetraacetyl-D-galactosamine (Ac4GalNAl) is a key metabolic probe reagent in the fields of glycobiology and chemical biology. As a chemically modified derivative of galactosamine, this compound achieves efficient and specific labeling and tracking of cellular metabolic pathways by integrating an alkynyl reporter group and an acetyl protecting group. Its design simulates natural sugar metabolic precursors, provides a powerful tool for studying glycosylation dynamics, cell surface engineering and disease mechanisms, and promotes progress from basic science to translational medicine.
Chemical Information
Chemical name: N-(4'-pentynoyl)-1,2,3,6-O-tetraacetyl-D-galactosamine
Common name: N-(4-pentynoyl)-galactosamine tetraacylated (Ac4GalNAl)
Chemical formula: C19H25NO10
Molecular weight: 427.41 g/mol
CAS number: 1658458-26-4
Category: Metabolic Probe Reagents
Structural features
Alkynyl functional group: The 4-pentynoyl side chain in the molecule introduces a terminal alkynyl group, allowing efficient, bioorthogonal ligation to azide-modified reporter molecules (e.g., fluorescent dyes, biotin) via copper-catalyzed azide-alkyne cycloaddition reaction (click chemistry). The reaction has strong specificity and mild conditions, minimizing interference with biological systems.
Acetylation modification: The 1, 2, 3, and 6 hydroxyl groups on the galactosamine ring are protected by acetyl groups, which significantly improves lipid solubility and cell membrane permeability. After entering cells, the acetyl group can be hydrolyzed by intracellular esterase to release active galactosamine derivatives, thereby participating in the natural metabolic process.
Precursor molecule characteristics: Ac4GalNAl is a biocompatible precursor molecule that can be taken up by cells and converted into UDP-galactosamine analogues through the sugar nucleotide synthesis pathway, and then used for glycoprotein and glycolipid synthesis by glycosyltransferases to achieve precise positioning of metabolic markers to newly synthesized glycoconjugates.
Main applications and advantages
Core tools for metabolic labeling and imaging
Ac4GalNA1 is widely used for labeling cell surface glycoconjugates. After cells take up the compound, they metabolically integrate it into membrane proteins and lipid sugar chains. Through click chemistry and coupling with fluorescent probes, high-contrast imaging can be achieved for immune cell tracking, tumor microenvironment visualization and neural cell network research. The inertness of the alkynyl label ensures long-term stability in living cells, allowing time-resolved tracking of glycosylation dynamics, providing key insights into metabolic regulation.
Promoter of glycobiology and disease research
As a galactosamine metabolism probe, Ac4GalNAl helps elucidate glycosyltransferase and glycosidase functions, revealing the role of sugar chains in cell recognition, signal transduction, and pathogen interaction. In infection biology, this compound can be used to mark host cell glycosylation changes and study pathogen adhesion mechanisms. Abnormal glycosylation is associated with cancer and autoimmune diseases. Using Ac4GalNAl for labeling can screen disease-related glycobiomarkers, providing a new strategy for early diagnosis.
Facilitator of drug development and targeted therapy
Based on the metabolic properties of Ac4GalNAl, a targeted drug delivery system can be designed. For example, coupling therapeutic molecules to metabolically labeled cells through click chemistry to achieve cell-specific targeting, enhance efficacy and reduce side effects has potential in cancer immunotherapy. In addition, this compound can be used to build a cell-based screening model to identify small molecule inhibitors or activators that regulate glucose metabolism, helping to develop treatments for metabolic diseases such as diabetes.
Conclusion
N-(4-pentynoyl)-galactosamine tetraacetyl ester (Ac4GalNAl) represents an achievement at the intersection of chemical biology and glycoscience. Its molecular design expands the boundaries of metabolic labeling technology and provides a multi-dimensional exploration platform for basic research and translational medicine. From decoding life processes to developing next-generation treatments, Ac4GalNAl continues to empower scientific discovery, heralding broad prospects in precision medicine and systems biology.
The above information is provided by the editor of KASONS and is for scientific research only.