Aminooxy-PEG4-CH2-Boc

Name: Aminooxy-PEG4-CH2-Boc
Brand: BOC Sciences
Rating: 5 (1 reviews)

CAS No.: 2062663-62-9

Cat No.: BP-500784 4.5

Aminooxy-PEG4-CH2-Boc is a heterobifunctional PEG linker featuring a free aminooxy group at one terminus and a Boc-protected carboxylate at the other, connected through a tetraethylene glycol spacer. The aminooxy functionality serves as a nucleophilic handle for chemoselective oxime ligation with aldehyde- or ketone-containing molecules, forming stable oxime bonds under mild physiological conditions without requiring metal catalysts or cytotoxic reagents. This bioorthogonal conjugation strategy is particularly valuable for site-specific attachment of carbonyl-bearing target protein ligands or E3 ubiquitin ligase-recruiting moieties. The Boc group protects the distal carboxylic acid during oxime ligation and can be removed under mild acidic conditions to reveal a free carboxylate for subsequent amide coupling with amine-containing ligands. The PEG spacer enhances aqueous solubility and provides the conformational flexibility necessary for productive ternary complex assembly between the target protein and the E3 ubiquitin ligase. The orthogonal reactivity of the aminooxy and carboxylate groups enables sequential, chemoselective installation of both functional ligands. Researchers employ this linker to leverage oxime-based bioconjugation in PROTAC assembly, investigating how this chemoselective ligation strategy influences degradation potency and modularity in targeted protein degradation research.

Structure of 2062663-62-9

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PROTAC Linker

Molecular Formula

C₁₄H₂₉NO₇

Molecular Weight

323.38

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

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Please store the product under the recommended conditions in the Certificate of Analysis.

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IUPACName

tert-butyl 2-[2-[2-[2-(2-aminooxyethoxy)ethoxy]ethoxy]ethoxy]acetate

InChI Key

YIWYEQPSYTYCHV-UHFFFAOYSA-N

InChI

InChI=1S/C14H29NO7/c1-14(2,3)22-13(16)12-20-9-8-18-5-4-17-6-7-19-10-11-21-15/h4-12,15H2,1-3H3

SMILES

CC(C)(C)OC(=O)COCCOCCOCCOCCON

This heterobifunctional linker presents a free aminooxy terminus and an acid-labile protected carboxyl group. It enables direct carbonyl-selective ligation while retaining a masked handle for later amide coupling, providing a flexible and polar spacer for modular PROTAC synthesis. Details follow below.

Structure: The linker contains a terminal aminooxy group, a flexible oligoether chain, and a tert-butyl acetate terminus. Its covalent framework includes nitrogen–oxygen, ether, and ester bonds; the aminooxy nitrogen is nucleophilic, whereas the ester masks the opposing carboxyl functionality.

Reactivity: Condense the aminooxy terminus with an aldehyde or ketone in mildly acidic aqueous-organic medium to form an oxime, with aniline-derived catalysts available when acceleration is needed. Avoid carbonyl-containing solvents and impurities that can consume the reagent. Acidic ester cleavage then reveals a carboxylic acid for standard activated amidation with an amine-bearing PROTAC component.

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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