Azido-PEG4-beta-D-glucose

 CAS No.: 1609083-15-9  Cat No.: BP-501363  Purity: 98% 4.5  

Azido-PEG4-β-D-glucose is a PEG-based, azide-functionalized glucose conjugate designed as a modular PROTAC linker building block. Structurally, it comprises a β-D-glucopyranose moiety connected through a short, four–ethylene glycol unit spacer to a terminal azide group, providing both hydrophilicity and a chemically “clickable” handle. In targeted protein degradation workflows, the azide enables efficient bioorthogonal conjugation (commonly via copper-catalyzed or strain-promoted azide–alkyne cycloaddition) to install or exchange the linker region between an E3 ligase ligand and a target-binding ligand. The PEG spacer helps tune linker flexibility and solvent exposure, while the glucose unit can be leveraged to improve aqueous solubility and to incorporate carbohydrate-recognition features when relevant to assay design. This reagent is valuable for researchers optimizing PROTAC architectures, facilitating rapid synthesis of linker variants, and supporting systematic structure–activity studies of degradation efficiency and cellular uptake.

Azido-PEG4-beta-D-glucose

Structure of 1609083-15-9

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Category
PROTAC Linker
Molecular Formula
C₁₄H₂₇N₃O₉
Molecular Weight
381.38

* For research and manufacturing use only. Not for human or clinical use.

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Purity
98%
Solubility
Water, DMSO, DMF
Storage
Please store the product under the recommended conditions in the Certificate of Analysis.
Shipping
Room temperature in continental US; may vary elsewhere.
IUPACName
(2R,3R,4S,5S,6R)-2-[2-[2-[2-(2-azidoethoxy)ethoxy]ethoxy]ethoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
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
InChI Key
AJCOHNWPGBTGTQ-RKQHYHRCSA-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
SMILES
C(COCCOCCOCCOC1C(C(C(C(O1)CO)O)O)O)N=[N+]=[N-]

Azido-PEG4-beta-D-glucose is a functional PEG-based linker designed for modular construction of PROTACs, enabling efficient conjugation of targeting ligands through a chemically addressable azide handle. Its PEG segment provides conformational flexibility and hydrophilicity, which can improve linker behavior in ternary-complex formation. The beta-D-glucose motif offers a defined stereochemical element for reliable functionalization. The following sections describe its structure and practical reactivity considerations in PROTAC synthesis.

Structure: The molecule comprises a PEG spacer bearing a terminal azide and a beta-D-glucose moiety. It contains ether linkages characteristic of PEG, a glycosidic framework from beta-D-glucose, and an azide functional group suitable for bioorthogonal coupling. Overall, it is polar and water-compatible.

Reactivity: The azide group is commonly used in copper-catalyzed azide–alkyne cycloaddition to connect to alkyne-bearing PROTAC components, proceeding via formation of a triazole linkage. Suitable conditions typically employ a Cu(I source with stabilizing ligands, an appropriate solvent such as aqueous or mixed aqueous systems, and controlled temperature to balance reaction rate and protein-ligand integrity. Alternative azide coupling routes include strain-promoted cycloaddition with cyclooctynes when copper-free handling is preferred.

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* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2

* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
g/mol
g

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