Boc-aminooxy-PEG2-propargyl

 CAS No.: 1895922-74-3  Cat No.: BP-500996  Purity: 98% 4.5  

Boc-aminooxy-PEG2-propargyl is a bifunctional, PEG-based linker reagent featuring a protected aminooxy group (Boc-protected), a short ethylene glycol chain (PEG2), and a terminal propargyl alkyne for bioorthogonal conjugation. The aminooxy functionality enables formation of stable oxime linkages with aldehyde-bearing targeting ligands, allowing controlled attachment to proteins or small-molecule warheads that can be functionalized with an aldehyde handle. The propargyl group supports copper-free or copper-catalyzed azide–alkyne cycloaddition (depending on the experimental setup), providing a robust route to connect the linker to azide-functional partners such as PROTAC scaffolds or degraders. In targeted protein degradation research, this type of linker is valuable for modular assembly of conjugates, improving synthetic flexibility while maintaining sufficient linker length and hydrophilicity to support solubility and minimize nonspecific interactions. Its orthogonal reactive handles facilitate stepwise construction and purification of PROTAC intermediates for mechanistic and optimization studies.

Boc-aminooxy-PEG2-propargyl

Structure of 1895922-74-3

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Category
PROTAC Linker
Molecular Formula
C₁₂H₂₁NO₅
Molecular Weight
259.30

* 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 N-[2-(2-prop-2-ynoxyethoxy)ethoxy]carbamate
Synonyms
t-Boc-aminooxy-PEG2-propargyl
InChI Key
XXPUFYWATPLMHN-UHFFFAOYSA-N
InChI
InChI=1S/C12H21NO5/c1-5-6-15-7-8-16-9-10-17-13-11(14)18-12(2,3)4/h1H,6-10H2,2-4H3,(H,13,14)
SMILES
CC(C)(C)OC(=O)NOCCOCCOCC#C

Boc-aminooxy-PEG2-propargyl is a PEG-based, bifunctional PROTAC linker building block designed to connect an aminooxy handle with a terminal alkyne for modular assembly. Its ether-rich PEG segment provides conformational flexibility and improved solubility, while the protected aminooxy group enables selective conjugation strategies commonly used in targeted protein degradation workflows. The following sections describe its structure and practical reactivity considerations for experimental PROTAC synthesis.

Structure: The molecule contains a Boc-protected aminooxy functionality linked through an ether-containing PEG segment to a propargyl (terminal alkyne) group. It features stable carbamate and ether linkages, with an alkyne suitable for chemoselective coupling. Overall, its PEG character supports favorable hydrophilicity and chain mobility.

Reactivity: For PROTAC construction, the Boc group is typically removed under standard acid-mediated deprotection to reveal the aminooxy nucleophile, which can then participate in oxime-forming conjugations with carbonyl-bearing partners. The terminal alkyne can be used in alkyne-compatible click-type coupling or other alkyne-directed chemistries depending on the partner functionality. Commonly, these steps are performed in polar organic solvents or aqueous mixtures with appropriate base and inert atmosphere when required.

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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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