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

 CAS No.: 2112737-20-7  Cat No.: BP-500617 4.5  

N-(Azido-PEG4)-N-Boc-PEG4-Boc is a branched polyethylene glycol linker featuring a central tertiary amine bearing three functional arms: an azide-terminated PEG chain, a Boc-protected carbamate arm, and a Boc-protected carboxylate arm. This multifunctional architecture enables orthogonal, stepwise conjugation strategies in PROTAC assembly. The azide group serves as a bioorthogonal handle for copper-catalyzed 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 particularly advantageous for constructing multivalent or heterobifunctional PROTACs, where two distinct ligands can be appended to a single linker scaffold through different chemistries. The extended PEG spacers enhance aqueous solubility and provide conformational flexibility critical for productive ternary complex formation between the target protein and the E3 ubiquitin ligase. Researchers employ this linker to explore branched degrader architectures and investigate how multivalent presentation of ligands influences degradation potency and selectivity.

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

Structure of 2112737-20-7

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PROTAC Linker
Molecular Formula
C₃₀H₅₈N₄O₁₂
Molecular Weight
666.80

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

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IUPACName
tert-butyl 3-[2-[2-[2-[2-[2-[2-[2-[2-(2-azidoethoxy)ethoxy]ethoxy]ethoxy]ethyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]ethoxy]ethoxy]ethoxy]ethoxy]propanoate
InChI Key
UZLWOPHRHVEWLM-UHFFFAOYSA-N
InChI
InChI=1S/C30H58N4O12/c1-29(2,3)45-27(35)7-11-37-15-19-41-23-25-43-21-17-39-13-9-34(28(36)46-30(4,5)6)10-14-40-18-22-44-26-24-42-20-16-38-12-8-32-33-31/h7-26H2,1-6H3
SMILES
CC(C)(C)OC(=O)CCOCCOCCOCCOCCN(CCOCCOCCOCCOCCN=[N+]=[N-])C(=O)OC(C)(C)C

This protected, heterofunctional oligoether linker supplies an azide for click conjugation together with masked amine and carboxyl functions for staged elaboration. Its flexible chain supports modular PROTAC construction and permits attachment of distinct ligand components. Structural and reaction characteristics are detailed below.

Structure: A carbamate-protected nitrogen joins oligoether segments terminating in an azide and a tert-butyl propanoate. The structure is rich in ether bonds and also contains carbamate and ester carbonyls; the flexible, polar chain separates its selectively addressable terminal groups.

Reactivity: Couple the azide with a terminal alkyne through a cuprous-catalyzed cycloaddition in water-compatible alcohol, dimethylformamide, or another mixed solvent, commonly with a stabilizing ligand and an ascorbate reductant. Acidic treatment can remove both the carbamate and tert-butyl ester protections, so the order of deprotection and subsequent amide coupling should be selected to preserve the attached ligands.

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L

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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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Historical Records: t-Boc-N-amido-PEG1-bromide | 3-(2-(benzyloxy)ethoxy)propan-1-ol | 2-[2-(Prop-2-yn-1-yloxy)ethoxy]acetic acid | PROTAC FAK degrader 1 | N-(PEG3-acid)-N-bis(PEG3-amine) | Aldehyde-benzyl-PEG5-alkyne | Boc-gly-PEG3-endo-BCN | N-Boc-N-bis(PEG3-NHS ester) | FmocNH-PEG4-t-butyl acetate | PROTAC RAR Degrader-1 | N-(Azido-PEG4)-N-Boc-PEG4-Boc

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