N-(Azido-PEG2)-N-Boc-PEG3-acid

 CAS No.: 2086689-01-0  Cat No.: BP-501105  Purity: 98% 4.5  

N-(Azido-PEG2)-N-Boc-PEG3-acid is a heterobifunctional polyethylene glycol (PEG) linker bearing a terminal azide handle, a Boc-protected amine, and a free carboxylic acid, enabling modular assembly of PROTACs and other targeted degradation conjugates. Structurally, it combines short PEG segments that provide aqueous solubility and conformational flexibility with an azide group suitable for bioorthogonal conjugation (e.g., copper-free or copper-catalyzed azide–alkyne cycloaddition) to attach this linker to complementary PROTAC components such as ligands or warheads. The Boc-protected amine can be deprotected to reveal an amine for coupling, while the carboxylic acid is already available for activation and amide-bond formation during PROTAC construction. In targeted protein degradation research, PEG-based spacers like this one can help tune linker length and reach, reduce steric hindrance at the ternary complex interface, and improve overall physicochemical properties, facilitating systematic structure–activity studies.

N-(Azido-PEG2)-N-Boc-PEG3-acid

Structure of 2086689-01-0

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Category
PROTAC Linker
Molecular Formula
C₂₀H₃₈N₄O₉
Molecular Weight
478.54

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

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Purity
98%
Solubility
Water, DMSO, DCM, 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
3-[2-[2-[2-[2-[2-(2-azidoethoxy)ethoxy]ethyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]ethoxy]ethoxy]ethoxy]propanoic acid
Synonyms
1-azido-9-(tert-butoxycarbonyl)-3,6,12,15,18-pentaoxa-9-azahenicosan-21-oic acid; 3-(2-{2-[2-(13-azido-2,2-dimethyl-4-oxo-3,8,11-trioxa-5-azatridecan-5-yl)ethoxy]ethoxy}ethoxy)propanoic acid; 5,8,11-Trioxa-2-azatetradecanedioic acid, 2-[2-[2-(2-azidoethoxy)ethoxy]ethyl]-, 1-(1,1-dimethylethyl) ester
InChI Key
NNNACCUYHDGKHF-UHFFFAOYSA-N
InChI
InChI=1S/C20H38N4O9/c1-20(2,3)33-19(27)24(6-10-30-14-13-29-9-5-22-23-21)7-11-31-15-17-32-16-12-28-8-4-18(25)26/h4-17H2,1-3H3,(H,25,26)
SMILES
CC(C)(C)OC(=O)N(CCOCCOCCN=[N+]=[N-])CCOCCOCCOCCC(=O)O

N-(Azido-PEG2)-N-Boc-PEG3-acid is a bifunctional PEG-based PROTAC linker designed to enable modular assembly of targeted protein degraders. Its azide handle supports bioorthogonal conjugation, while the protected acid functionality and PEG spacers support effective solubility and controlled spatial presentation of ligands. These features make it well suited for constructing PROTACs where linker flexibility and reliable coupling chemistry are critical; detailed structural and reactivity considerations are provided below.

Structure: The linker contains polyethylene glycol segments that provide hydrophilicity and conformational flexibility, an azide functional group for click-type coupling, and a carboxylic acid motif for subsequent derivatization. A Boc-protected amine is present to manage reactivity during stepwise synthesis. Ether linkages dominate the backbone.

Reactivity: The azide group is typically engaged via copper-catalyzed azide–alkyne cycloaddition or related azide-compatible conjugation strategies, enabling efficient attachment to alkyne-bearing partners under mild conditions. The Boc group is commonly removed using acid to reveal an amine for amide or urea-forming coupling. Carboxylic acid activation (e.g., carbodiimide-based) supports amide bond formation in standard PROTAC linker assembly workflows, often using polar aprotic solvents.

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Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2

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Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
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