
Azido-PEG4-beta-D-glucose | CAS 1609083-15-9
| Catalog Number | R14-0017 |
| Category | Azides |
| Molecular Formula | C₁₄H₂₇N₃O₉ |
| Molecular Weight | 381.38 |
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Product Introduction
Azido-PEG4-beta-D-glucose is a polyethylene glycol (PEG)-based PROTAC linker. Azido-PEG4-beta-D-glucose can be used in the synthesis of a series of PROTACs.
Chemical Information
Product Specification
Application
Computed Properties
Patents
Chemical Information
| Synonyms | (2R,3R,4S,5S,6R)-2-(2-(2-(2-(2-azidoethoxy)ethoxy)ethoxy)ethoxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol; (2R,3R,4S,5S,6R)-2-(2-{2-[2-(2-azidoethoxy)ethoxy]ethoxy}ethoxy)-6-(hydroxymethyl)oxane-3,4,5-triol |
| Purity | 98% |
| IUPAC Name | (2R,3R,4S,5S,6R)-2-[2-[2-[2-(2-azidoethoxy)ethoxy]ethoxy]ethoxy]-6-(hydroxymethyl)oxane-3,4,5-triol |
| SMILES | C(COCCOCCOCCOC1C(C(C(C(O1)CO)O)O)O)N=[N+]=[N-] |
| InChI | InChI=1S/C14H27N3O9/c15-17-16-1-2-22-3-4-23-5-6-24-7-8-25-14-13(21)12(20)11(19)10(9-18)26-14/h10-14,18-21H,1-9H2/t10-,11-,12+,13-,14-/m1/s1 |
| InChIKey | AJCOHNWPGBTGTQ-RKQHYHRCSA-N |
| Solubility | Water, DMSO, DMF |
Product Specification
| Storage | Please store the product under the recommended conditions in the Certificate of Analysis. |
Application
Azido-PEG4-beta-D-glucose is a PEGylated azide-functionalized glycoside designed for copper-free or copper-mediated click chemistry workflows. As an azide-bearing carbohydrate handle, it is commonly used as a bioorthogonal “sugar tag” to install β-D-glucose motifs onto surfaces, polymers, and biomolecules with high chemoselectivity. The flexible PEG4 spacer helps reduce steric constraints around the sugar, making the reagent particularly relevant for glycoconjugate construction in chemical biology, biomaterials, and molecular imaging tool development.
1. Glycoconjugate Surface Engineering
Azido-PEG4-beta-D-glucose is widely used to decorate material surfaces and interfaces with β-D-glucose recognition elements for studying carbohydrate-mediated interactions and for building defined glycocalyx-mimetic coatings. Researchers incorporate the azide handle into click-compatible substrates to generate stable, multivalent sugar presentations on hydrogels, polymer films, and functionalized nanoparticles. The PEG4 linker is especially useful when tuning surface accessibility of the carbohydrate while maintaining colloidal stability and minimizing nonspecific adsorption in downstream assays.
2. Click-Driven Imaging Probe Construction
Azido-PEG4-beta-D-glucose serves as a practical sugar component for assembling imaging and detection probes that require a β-D-glucose motif for targeting carbohydrate-binding processes in vitro. Probe developers use the azide group to attach fluorophores, affinity tags, or imaging reporters to glucose-bearing constructs via click conjugation, enabling modular probe libraries for screening and method development. The PEG4 spacer supports consistent labeling density and improved solubility, which is valuable when preparing conjugates for microscopy, flow-based readouts, or optical/affinity detection workflows.
3. Polymer and Hydrogel Functionalization
Azido-PEG4-beta-D-glucose is commonly employed to introduce glucose-functional groups into click-reactive polymers and hydrogels, where the carbohydrate functionality can be used to regulate cell-material interactions, biomolecular binding, or transport properties in experimental biomaterials platforms. Materials scientists leverage the azide handle to crosslink or post-functionalize PEG-based networks and other click-compatible matrices, generating tunable glycoconjugate architectures. This approach supports reproducible fabrication of sugar-decorated materials while allowing independent control over polymer chemistry and glucose presentation.
4. Enzyme Substrate and Binding Studies
Azido-PEG4-beta-D-glucose is frequently used as a glucose analog building block for constructing defined conjugate substrates and ligands used in carbohydrate-binding and enzyme-assay development. Chemical biology teams incorporate the reagent into click-assembled conjugates to create multivalent or surface-tethered glucose motifs, supporting mechanistic studies of lectin interactions and carbohydrate recognition in controlled experimental settings. The PEG4 spacer helps maintain accessibility of the β-D-glucose moiety, which is important for comparing binding behavior across conjugate formats and for generating standardized reagents for assay workflows.
Computed Properties
| XLogP3 | -1.6 |
| Hydrogen Bond Donor Count | 4 |
| Hydrogen Bond Acceptor Count | 11 |
| Rotatable Bond Count | 14 |
| Exact Mass | 381.17472945 g/mol |
| Monoisotopic Mass | 381.17472945 g/mol |
| Topological Polar Surface Area | 141Ų |
| Heavy Atom Count | 26 |
| Formal Charge | 0 |
| Complexity | 411 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 5 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Covalently-Bonded Unit Count | 1 |
| Compound Is Canonicalized | Yes |
Patents
| Publication Number | Title | Priority Date |
|---|---|---|
| US-2022047708-A1 | Glucose sensitive insulins and uses thereof | 2018-09-19 |
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