N-(Azido-PEG2)-N-Boc-PEG4-Boc

 CAS No.: 2093153-83-2  Cat No.: BP-500869  Purity: 98% 4.5  

N-(Azido-PEG2)-N-Boc-PEG4-Boc is a branched polyethylene glycol linker featuring a central tertiary amine bearing three functional arms: an azide-terminated short PEG chain, a Boc-protected carbamate arm, and a Boc-protected carboxylate arm. This multifunctional architecture enables orthogonal, stepwise conjugation in PROTAC assembly. The azide group serves as a bioorthogonal handle for copper-catalyzed or strain-promoted azide-alkyne cycloaddition, allowing selective coupling to alkyne-functionalized ligands. The Boc-protected carbamate can be selectively removed under mild acidic conditions to liberate a secondary amine for further functionalization, while the Boc-protected carboxylate, upon deprotection, provides a free carboxylic acid for amide bond formation with amine-containing warheads or E3 ligase-recruiting moieties. The branched topology is advantageous for constructing heterobifunctional PROTACs where two distinct ligands can be appended to a single linker scaffold through different chemistries, with the azide providing a third orthogonal handle. The PEG spacers enhance aqueous solubility and provide conformational flexibility critical for productive ternary complex formation. Researchers employ this linker to explore branched degrader architectures and to investigate how orthogonal, multi-handle conjugation strategies influence degradation potency, selectivity, and modularity in targeted protein degradation research.

N-(Azido-PEG2)-N-Boc-PEG4-Boc

Structure of 2093153-83-2

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Category
PROTAC Linker
Molecular Formula
C₂₆H₅₀N₄O₁₀
Molecular Weight
578.70

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

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Purity
98%
Storage
Please store the product under the recommended conditions in the Certificate of Analysis.
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Room temperature in continental US; may vary elsewhere.
IUPACName
tert-butyl 3-[2-[2-[2-[2-[2-[2-(2-azidoethoxy)ethoxy]ethyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]ethoxy]ethoxy]ethoxy]ethoxy]propanoate
Synonyms
N-(Azido-PEG2)-N-Boc-PEG4-t-butyl ester
InChI Key
WILFBOXOPLSLTM-UHFFFAOYSA-N
InChI
InChI=1S/C26H50N4O10/c1-25(2,3)39-23(31)7-11-33-15-19-37-21-22-38-20-18-36-14-10-30(24(32)40-26(4,5)6)9-13-35-17-16-34-12-8-28-29-27/h7-22H2,1-6H3
SMILES
CC(C)(C)OC(=O)CCOCCOCCOCCOCCN(CCOCCOCCN=[N+]=[N-])C(=O)OC(C)(C)C

This protected oligoether linker integrates an azide with latent amine and carboxyl functions, enabling staged construction of a heterobifunctional degrader. Its unequal arms offer compact geometric control, while click compatibility and removable protections support modular PROTAC synthesis. Detailed structural and reactive information follows.

Structure: A carbamate-protected nitrogen connects an azido-terminated oligoether segment and a longer oligoether chain ending as tert-butyl propanoate. The molecule contains ether bonds, carbamate and ester carbonyls, a terminal azide, and flexible carbon–nitrogen linkages.

Reactivity: The azide can be joined to a terminal alkyne by cuprous-catalyzed cycloaddition in a polar aqueous-organic medium using a coordinating ligand and reducing agent. Acidic conditions remove the nitrogen carbamate and tert-butyl ester protections, potentially exposing both amine and acid together. A planned sequence with temporary protection, selective acylation, or prior click assembly helps prevent intramolecular or intermolecular side reactions.

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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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* Total Molecular Weight:
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Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
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Historical Records: Azido-PEG9-t-butyl ester | 1-(t-Boc-Aminooxy)-3-aminooxy-propane | 4-Maleimidobutyric acid | N-(Azido-PEG2)-N-Fluorescein-PEG3-acid | TL 12-186 | GSK1324726A | Amino-PEG24-alcohol | (3-[2-Aminoethyl)dithio]propionic acid HCl | N-(m-PEG4)-N'-(PEG4-NHS ester)-Cy5 | m-PEG2-4-nitrophenyl carbonate | N-(Azido-PEG2)-N-Boc-PEG4-Boc

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