
Ac4ManNAl | CAS 935658-93-8
| Catalog Number | R02-0040 |
| Category | Alkynes |
| Molecular Formula | C19H25NO10 |
| Molecular Weight | 427.40 |
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Product Introduction
Ac4GalNAl is an alkyne-labeled monosaccharide that provides a highly specific tool for studying glycoproteins through metabolic labeling in vivo and subsequent chemoselective ligation.
Chemical Information
Application
Chemical Information
| Synonyms | N-(4-Pentynoyl) mannosamine tetraacylated; N-(4-pentynoyl)-galactosamine-tetraacylated; 2-[(1-Oxo-4-pentynyl)amino]-1-O,3-O,4-O,6-O-tetraacetyl-2-deoxy-D-mannopyranose |
| IUPAC Name | [(2R,3S,4R,5S)-3,4,6-triacetyloxy-5-(pent-4-ynoylamino)oxan-2-yl]methyl acetate |
| SMILES | CC(=O)OCC1C(C(C(C(O1)OC(=O)C)NC(=O)CCC#C)OC(=O)C)OC(=O)C |
| InChI | InChI=1S/C19H25NO10/c1-6-7-8-15(25)20-16-18(28-12(4)23)17(27-11(3)22)14(9-26-10(2)21)30-19(16)29-13(5)24/h1,14,16-19H,7-9H2,2-5H3,(H,20,25)/t14-,16+,17-,18-,19?/m1/s1 |
| InChIKey | PODQGPKRSTUNAT-APCIHPPFSA-N |
| Appearance | White Solid |
Application
Ac4ManNAl is a specialized click-chemistry reagent built on an acetylated sugar scaffold designed for bioorthogonal labeling workflows. As a cyclooctyne/strained-alkyne–type functional handle is commonly leveraged in copper-free click strategies, this reagent is widely used to install a defined alkyne-bearing sugar motif onto biological targets. The acetylated form supports cell-compatible uptake and subsequent intracellular deprotection, enabling downstream conjugation to biomolecules, surfaces, and imaging platforms. In research and materials settings, Ac4ManNAl serves as a practical precursor for glycan-functional probes where controlled sugar presentation is essential.
1. Glycan Labeling Workflows
Ac4ManNAl is used to introduce a clickable sugar unit into glycan structures for mapping and comparative profiling of carbohydrate presentation in cell-based assays. Researchers incorporate it into metabolic labeling or glycomics sample preparation pipelines to generate azide/alkyne-reactive glycan analogs that can be further conjugated to reporter tags, affinity handles, or enrichment reagents. The acetylated sugar design supports efficient delivery into experimental systems, while the alkyne handle enables orthogonal coupling to fluorescent dyes, biotin derivatives, or polymerizable reporters for downstream analysis and visualization.
2. Molecular Imaging Probes
Ac4ManNAl is commonly employed in the development of carbohydrate-targeted imaging reagents where fluorescent or luminescent readouts are attached after click conjugation. After the sugar motif is incorporated into glycoconjugates, the alkyne functionality allows rapid attachment of imaging moieties such as fluorophores or quencher–reporter pairs through copper-free click-compatible strategies. This use case is particularly relevant for building multicomponent probes that require a defined glycan display density, enabling consistent probe architectures for microscopy, flow-based readouts, and imaging reagent optimization.
3. Surface And Biomaterial Functionalization
Ac4ManNAl supports materials chemistry efforts that require controlled installation of sugar ligands onto engineered surfaces and biomaterial coatings. By using the clickable handle to attach sugars to substrates or to crosslinkable linker systems, researchers can create glycan-functional interfaces for studying biomolecular recognition, cell-surface interactions, and ligand presentation effects in vitro. The reagent’s sugar-based structure is well matched to workflows that aim to mimic extracellular carbohydrate patterns on hydrogels, polymer films, and assay surfaces, where subsequent click coupling provides modularity in probe or ligand density.
4. Diagnostic Reagent Development
Ac4ManNAl is used in the construction of carbohydrate-based diagnostic research reagents that rely on modular conjugation of sugar motifs to detection formats. In assay development, the reagent can be incorporated into glycan analogs that are then clicked to reporter systems such as fluorescent labels, enzyme-linked tags, or affinity capture elements used in analytical workflows. This approach is valued for enabling reproducible reagent architectures, supporting multiplexing strategies, and providing a practical route to standardized glycan-functional components used in biochemical characterization and diagnostic assay prototyping.
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