1,3,4,6-Tetra-O-acetyl-N-azidoacetylgalactosamine | CAS 653600-56-7

Catalog Number	R14-0013
Category	Azides
Molecular Formula	C16H22N4O10
Molecular Weight	430.37

Catalog Number	Size	Price	Quantity
R14-0013	50 mg	$499
R14-0013	200 mg	$1799

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Product Introduction

1,3,4,6-Tetra-O-acetyl-N-azidoacetylgalactosamine is an acetylated azido sugar derivative presented as a crystalline powder, ideal for advanced glycoscience research. Featuring both azido and acetyl functional groups, it demonstrates enhanced cell permeability and stability in aqueous environments. Widely utilized as a metabolic chemical reporter, it enables bioorthogonal labeling of glycoproteins and glycoconjugates. Researchers employ this compound in studies of glycan biosynthesis, metabolic engineering, and click chemistry applications.

Chemical Information
Product Specification
Application

Chemical Information

Synonyms	N-azidoacetylgalactosamine-tetraacylated (Ac4GalNAz); GalNAz tetraacetate; Ac4GalNAz; D-Galactopyranose, 2-[(2-azidoacetyl)amino]-2-deoxy-, 1,3,4,6-tetraacetate; D-Galactopyranose, 2-[(azidoacetyl)amino]-2-deoxy-, 1,3,4,6-tetraacetate
Purity	≥95%
IUPAC Name	[(2R,3R,4R,5R)-3,4,6-triacetyloxy-5-[(2-azidoacetyl)amino]oxan-2-yl]methyl acetate
SMILES	CC(=O)OCC1C(C(C(C(O1)OC(=O)C)NC(=O)CN=[N+]=[N-])OC(=O)C)OC(=O)C
InChI	InChI=1S/C16H22N4O10/c1-7(21)26-6-11-14(27-8(2)22)15(28-9(3)23)13(16(30-11)29-10(4)24)19-12(25)5-18-20-17/h11,13-16H,5-6H2,1-4H3,(H,19,25)/t11-,13-,14+,15-,16?/m1/s1
InChIKey	HGMISDAXLUIXKM-YJUJGKJLSA-N
Appearance	White to off-white powder

Product Specification

Storage

Store at -20°C

Application

1,3,4,6-Tetra-O-acetyl-N-azidoacetylgalactosamine is a cell-permeable, protected azido-sugar building block designed for bioorthogonal labeling workflows. As an azide-bearing monosaccharide derivative, it is commonly used in azide-compatible click chemistry strategies to introduce galactosamine motifs into glycoconjugates. The tetra-O-acetyl protection pattern supports uptake and subsequent deprotection in biological or material contexts, making it a practical reagent for constructing azide-functional glycan structures used in chemical biology and molecular imaging experiments.

1. Glycan Labeling In Cells

1,3,4,6-Tetra-O-acetyl-N-azidoacetylgalactosamine is widely used in metabolic or biosynthetic glycan labeling to install azide handles on cell-surface and intracellular glycoconjugates. Researchers employ it to generate azide-functional glycans that can be selectively tagged with complementary click partners for downstream visualization, enrichment, or profiling. This approach is particularly valuable when the goal is to compare glycan remodeling under different experimental conditions while maintaining a consistent chemical handle for affinity capture and detection.

2. Click-Based Probe Conjugation

1,3,4,6-Tetra-O-acetyl-N-azidoacetylgalactosamine provides an azide functionality that can be carried through to subsequent click conjugation steps, enabling the attachment of diverse reporters such as fluorophores, affinity tags, or mass spectrometry–compatible groups. In chemical biology workflows, the reagent is used to generate azide-bearing glycan substrates that can be coupled to imaging probes or enrichment reagents, supporting experiments that require selective labeling with minimal cross-reactivity. The protected sugar framework helps deliver the azide functionality into glycoconjugate contexts where direct labeling would be less convenient.

3. Glycoproteomics And Enrichment

1,3,4,6-Tetra-O-acetyl-N-azidoacetylgalactosamine is used to introduce clickable azide groups into glycoprotein populations, supporting glycoproteomics strategies that rely on selective capture. After incorporation into glycans, click chemistry enables attachment of biotin or other affinity ligands, facilitating enrichment of labeled glycoproteins or glycopeptides prior to LC-MS analysis. This application is common in studies aiming to map glycosylation patterns, quantify relative changes, and improve detection sensitivity by reducing sample complexity.

4. Imaging Of Glycan Dynamics

1,3,4,6-Tetra-O-acetyl-N-azidoacetylgalactosamine is applied in molecular imaging workflows that require tracking glycan incorporation and turnover using click-compatible fluorescent or luminescent reporters. By generating azide-functional glycans, the reagent supports spatial and temporal labeling strategies where the readout is introduced via a subsequent click step. Such usage is common in microscopy-based studies and imaging reagent development, where consistent chemical tagging of glycan structures is essential for comparing experimental conditions and constructing imaging-ready conjugates.