Propargyl-PEG10-COOtBu

 CAS No.: 2055022-22-3  Cat No.: BP-500701  Purity: ≥95% 4.5  

Propargyl-PEG10-COOtBu is a PEG-based PROTAC linker featuring a terminal propargyl (alkyne) handle and a protected carboxylate at the opposite end, enabling orthogonal functionalization during linker assembly. The structure comprises a polyethylene glycol chain of approximately ten ethylene oxide units, which provides conformational flexibility and aqueous solubility while spacing the two conjugation sites to reduce steric interference. In PROTAC design, such bifunctional linkers are used to connect a ligand for a target protein to a ligand for an E3 ligase, typically through click-compatible coupling at the propargyl terminus and subsequent deprotection or carboxyl-directed chemistry at the C-terminal end. The PEG spacer can improve effective intramolecular reach and promote productive ternary complex formation, supporting efficient ubiquitination and degradation. This compound is therefore valuable for constructing degraders where controlled linker length, hydrophilicity, and modular attachment chemistry are critical for optimizing degradation potency and selectivity.

Propargyl-PEG10-COOtBu

Structure of 2055022-22-3

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Category
PROTAC Linker
Molecular Formula
C28H52O12
Molecular Weight
580.71
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-[2-(2-prop-2-ynoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]propanoate
Synonyms
Propargyl-PEG10-t-butyl ester; Propargyl-PEG10-Boc; tert-butyl 2-((prop-2-yn-1-yloxy)methyl)-3,6,9,12,15,18,21,24,27-nonaoxanonacosanoate
Boiling Point
592.3±45.0 °C at 760 mmHg
Density
1.1±0.1 g/cm3
InChI Key
AQCJITMVJIOAQF-UHFFFAOYSA-N
InChI
InChI=1S/C28H52O12/c1-5-7-30-9-11-32-13-15-34-17-19-36-21-23-38-25-26-39-24-22-37-20-18-35-16-14-33-12-10-31-8-6-27(29)40-28(2,3)4/h1H,6-26H2,2-4H3
SMILES
CC(C)(C)OC(=O)CCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCC#C

This Propargyl-PEG10-COOtBu linker is designed for modular PROTAC synthesis, providing a chemically addressable propargyl handle for orthogonal conjugation and a protected carboxylate for controlled downstream functionalization. Its PEG-based spacer supports productive ternary complex formation by improving solubility and conformational flexibility. The subsequent points describe the structure and practical reactivity considerations for constructing PROTACs using this linker.

Structure: The linker contains a poly(ethylene glycol) chain that confers hydrophilicity and flexible spacing, capped with a terminal propargyl group and a tert-butyl-protected carboxylate. It features ether linkages along the PEG backbone, an alkyne suitable for bioorthogonal coupling, and ester/acid protection chemistry at the carboxyl terminus.

Reactivity: The propargyl group enables copper-catalyzed azide–alkyne cycloaddition or related alkyne-based conjugation strategies under standard click-chemistry conditions, typically using a Cu(I) source and an appropriate solvent system compatible with sensitive warheads. The tert-butyl ester can be deprotected to reveal the carboxylic acid using acid-mediated cleavage, allowing subsequent amide or ester bond formation with activated carboxyl derivatives.

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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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g/mol
Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
g/mol
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