Propargyl-PEG4-NHBoc

 CAS No.: 1219810-90-8  Cat No.: BP-500671  Purity: ≥95% 4.5  

Propargyl-PEG4-NHBoc is a polyethylene glycol (PEG) linker bearing a terminal propargyl (alkyne) group and an N-Boc-protected amine at the opposite end, providing a flexible, water-compatible chain of four ethylene glycol units. The PEG segment functions as a hydrophilic spacer that can reduce steric interference and improve the effective reach between a ligand-binding warhead and an E3 ligase recruiter in PROTAC constructs. The terminal alkyne enables chemoselective conjugation via copper-catalyzed azide–alkyne cycloaddition or related click-type coupling strategies, facilitating modular assembly under mild conditions. The Boc-protected amine serves as a protected handle for subsequent deprotection and coupling to electrophiles or activated carboxylic acids, allowing controlled formation of amide or related linkages. In targeted protein degradation research, this linker supports systematic tuning of linker length, polarity, and attachment geometry, which are key determinants of ternary complex formation and degradation potency.

Propargyl-PEG4-NHBoc

Structure of 1219810-90-8

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Category
PROTAC Linker
Molecular Formula
C16H29NO6
Molecular Weight
331.40
Related CAS
1520979-34-3 (polymer)
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 DCM, DMF, DMSO
Appearance
Pale Yellow Oily Matter
Storage
Store at -20°C
Shipping
Room temperature in continental US; may vary elsewhere.
IUPACName
tert-butyl N-[2-[2-[2-(2-prop-2-ynoxyethoxy)ethoxy]ethoxy]ethyl]carbamate
Synonyms
t-Boc-N-Amido-PEG4-propargyl;t-Boc-N-Amido-PEG4-Propargyl; Boc-N-Amido-PEG4-propargyl; tert-Butyl 3,6,9,12-tetraoxapentadec-14-yn-1-ylcarbamate; Boc-N-Amido-PEG4-Alkyne; 2-Methyl-2-propanyl 3,6,9,12-tetraoxapentadec-14-yn-1-ylcarbamate; Carbamic acid, N-3,6,9,12-tetraoxapentadec-14-yn-1-yl-, 1,1-dimethylethyl ester
Boiling Point
426.0±40.0°C at 760 mmHg
Density
1.1±0.1 g/cm3
InChI Key
AHCBQLUQQSACBL-UHFFFAOYSA-N
InChI
InChI=1S/C16H29NO6/c1-5-7-19-9-11-21-13-14-22-12-10-20-8-6-17-15(18)23-16(2,3)4/h1H,6-14H2,2-4H3,(H,17,18)
SMILES
CC(C)(C)OC(=O)NCCOCCOCCOCCOCC#C

Propargyl-PEG4-NHBoc is a PEG-based, bifunctional PROTAC linker designed to connect a propargyl handle to an orthogonally protected amine, enabling modular assembly of targeted protein degraders. Its ether-rich PEG segment supports solubility and conformational flexibility, while the terminal alkyne provides a reliable chemical “attachment point” for bioorthogonal conjugation strategies. The protected amine facilitates controlled coupling steps during PROTAC synthesis, and the molecule is described in detail below.

Structure: The linker comprises a poly(ethylene glycol) chain containing ether linkages, terminating in a propargyl group and a Boc-protected amine. It features a terminal alkyne suitable for click-type reactions and a carbamate protecting group that improves synthetic selectivity and stability under coupling conditions.

Reactivity: The terminal alkyne can participate in copper-catalyzed azide–alkyne cycloaddition or related alkyne conjugation workflows, typically requiring an appropriate catalyst system and compatible, degassed solvents. The Boc group is removable under standard acid-mediated deprotection to reveal a primary amine for subsequent amide or urea-forming couplings. Orthogonality enables stepwise PROTAC construction while minimizing side reactions.

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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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