Propargyl-PEG8-COOtBu

 CAS No.: 2055014-96-3  Cat No.: BP-500811  Purity: ≥95% 4.5  

Propargyl-PEG8-COOtBu is a heterobifunctional polyethylene glycol (PEG) linker featuring a terminal propargyl group for alkyne-based conjugation and a protected carboxylate (tert-butyl ester) at the opposite end. The PEG8 chain provides a flexible, hydrophilic spacer that can reduce steric hindrance and improve productive engagement between a targeting ligand and an E3 ligase ligand in PROTAC constructs. In targeted protein degradation workflows, the terminal alkyne enables site-specific attachment through copper-catalyzed azide–alkyne cycloaddition or related click chemistries, while subsequent deprotection of the tert-butyl ester yields a carboxylic acid handle suitable for coupling to other PROTAC fragments. This linker is valuable for researchers optimizing linker length and polarity to tune degradation potency, cellular permeability, and overall physicochemical properties of PROTACs, while maintaining modular synthetic flexibility for structure–activity relationship studies.

Propargyl-PEG8-COOtBu

Structure of 2055014-96-3

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Category
PROTAC Linker
Molecular Formula
C24H44O10
Molecular Weight
492.61
Appearance
Pale Yellow or Colorless Oily Matter

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

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Purity
≥95%
Solubility
Soluble in Water, DMSO, DCM, DMF
Appearance
Pale Yellow or Colorless 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 3-[2-[2-[2-[2-[2-[2-(2-prop-2-ynoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]propanoate
Synonyms
Propargyl-PEG8-t-butyl ester; Propargyl-PEG8-Boc; tert-butyl 4,7,10,13,16,19,22,25-octaoxaoctacos-27-ynoate
Boiling Point
528.4±45.0 °C at 760 mmHg
Density
1.1±0.1 g/cm3
InChI Key
IGEMRRCREJIMCQ-UHFFFAOYSA-N
InChI
InChI=1S/C24H44O10/c1-5-7-26-9-11-28-13-15-30-17-19-32-21-22-33-20-18-31-16-14-29-12-10-27-8-6-23(25)34-24(2,3)4/h1H,6-22H2,2-4H3
SMILES
CC(C)(C)OC(=O)CCOCCOCCOCCOCCOCCOCCOCCOCC#C

Propargyl-PEG8-COOtBu is a PEG-based PROTAC linker designed to combine a bioorthogonal handle with a protected carboxylate functionality, enabling modular assembly of targeted protein degraders. Its flexible poly(ethylene glycol) segment can promote productive ternary-complex formation by improving linker solubility and conformational adaptability. The propargyl group supports click-type conjugation strategies, while the tert-butyl-protected carboxylate facilitates downstream functionalization. Detailed structural and synthetic considerations are provided below for experimental planning.

Structure: The linker contains a PEG chain that provides flexible, ether-rich connectivity, terminating in a propargyl moiety and a tert-butyl-protected carboxylate. It features carbon–carbon and carbon–oxygen bonds, including an alkyne suitable for selective coupling, and an ester protecting group that can be removed under controlled conditions.

Reactivity: The propargyl functionality is compatible with copper(I)-catalyzed azide–alkyne cycloaddition or related alkyne click conjugation approaches to connect PROTAC fragments. The tert-butyl ester can be cleaved to reveal a free carboxylic acid for amide or ester coupling, typically using acidolysis conditions. Common solvents include polar aprotic media for coupling steps, and reaction setups should consider alkyne stability and orthogonality to other functional groups.

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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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