Propargyl-PEG4-OCH2-Boc

 CAS No.: 2098489-63-3  Cat No.: BP-500885  Purity: ≥95% 4.5  

Propargyl-PEG4-OCH2-Boc is a heterobifunctional PEG linker featuring a terminal propargyl group at one terminus and a Boc-protected carboxylate at the other, connected through a tetraethylene glycol spacer with an intervening methylene unit. The propargyl group provides a terminal alkyne that serves as a bioorthogonal handle for copper-catalyzed azide-alkyne cycloaddition, enabling highly selective and efficient conjugation to azide-functionalized target protein ligands or E3 ubiquitin ligase-recruiting moieties under mild aqueous conditions. This click chemistry approach is widely employed in PROTAC synthesis due to its quantitative yields, broad functional group tolerance, and compatibility with sensitive biomolecules. The Boc group protects the distal carboxylic acid during click conjugation and can be removed under standard 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. Researchers utilize this linker to leverage click chemistry-based bioconjugation in PROTAC assembly, investigating how this modular conjugation strategy influences degradation potency and selectivity in targeted protein degradation studies.

Propargyl-PEG4-OCH2-Boc

Structure of 2098489-63-3

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Category
PROTAC Linker
Molecular Formula
C17H30O7
Molecular Weight
346.41
Appearance
Pale Yellow Oily Matter

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

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Purity
≥95%
Solubility
Soluble in DMSO
Appearance
Pale Yellow Oily Matter
Storage
Store at 2-8°C for short term (days to weeks) or -20°C for long term (months to years)
Shipping
Room temperature in continental US; may vary elsewhere.
IUPACName
tert-butyl 2-[2-[2-[2-(2-prop-2-ynoxyethoxy)ethoxy]ethoxy]ethoxy]acetate
Synonyms
Propargyl-PEG5-CH2COOtBu; Propargyl-PEG5-CH2CO2tBu; Propargyl-PEG4-O-C1-Boc; 3,6,9,12,15-Pentaoxaoctadec-17-ynoic acid, 1,1-dimethylethyl ester; Propargyl-PEG5-CH2COOH t-Bu Ester; 2-Methyl-2-propanyl 3,6,9,12,15-pentaoxaoctadec-17-yn-1-oate; tert-butyl 3,6,9,12,15-pentaoxaoctadec-17-ynoate
Boiling Point
406.8±40.0°C (Predicted)
Density
1.055±0.06 g/cm3 (Predicted)
InChI Key
ZYUYTWWDQAPZRS-UHFFFAOYSA-N
InChI
InChI=1S/C17H30O7/c1-5-6-19-7-8-20-9-10-21-11-12-22-13-14-23-15-16(18)24-17(2,3)4/h1H,6-15H2,2-4H3
SMILES
CC(C)(C)OC(=O)COCCOCCOCCOCCOCC#C

This heterobifunctional oligoether linker combines a terminal alkyne with an acid-labile protected carboxyl group. It supports reliable click attachment to an azide-bearing ligand and subsequent amide formation, providing a flexible, polar spacer for convergent PROTAC assembly. Structural and reaction details follow.

Structure: The molecule contains a propargyl ether at one end, an oligoether chain, and a tert-butyl acetate at the other. Its framework features a terminal carbon–carbon triple bond, multiple ether bonds, flexible methylene groups, and a protected ester carbonyl.

Reactivity: Join the terminal alkyne to an azide by cuprous-catalyzed cycloaddition in aqueous alcohol, dimethylformamide, or another compatible polar medium, using a copper ligand and reductant when copper is generated in situ. Acidic cleavage then releases the carboxylic acid from the tert-butyl ester. Carbodiimide- or uronium-mediated activation enables coupling to an amine-bearing PROTAC partner under basic, anhydrous conditions.

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L

* 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

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* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
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Historical Records: Amino-PEG3-t-butyl ester | Tetraethylene glycol dimethyl ether | N-(m-PEG4)-N'-(PEG2-NHS ester)-Cy5 | PROTAC CRABP-II Degrader-1 | Benzyl-PEG11-Ms | Ald-Ph-PEG24-NHS ester | Propargyl-PEG14-Boc | Azido-PEG9-NHS ester | BSJ-4-116 | Br-PEG4-COOtBu | Propargyl-PEG4-OCH2-Boc

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