Amino-PEG4-acetic acid

 CAS No.: 195071-49-9  Cat No.: BP-500267  Purity: >98.0% 4.5  

Amino-PEG4-acetic acid is a heterobifunctional polyethylene glycol (PEG) linker bearing a terminal primary amine and a carboxylic acid, providing a flexible, hydrophilic spacer of approximately four ethylene glycol units. In PROTAC and related targeted protein degradation constructs, such PEG-based linkers are used to tune the spatial arrangement between the ligand that engages the target protein and the ligand that recruits an E3 ubiquitin ligase. The amine and carboxyl groups enable straightforward conjugation strategies, including amide coupling to carboxyl-activated ligands or formation of amide/urea linkages after appropriate functional group activation, while the PEG segment improves solubility and can reduce steric interference at the ternary complex interface. This linker is valuable for systematic linker-length and attachment-position optimization, helping researchers balance potency, degradation efficiency, and physicochemical properties in experimental PROTAC design.

Amino-PEG4-acetic acid

Structure of 195071-49-9

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Category
PROTAC Linker
Molecular Formula
C10H21NO6
Molecular Weight
251.28
Appearance
Pale Yellow Oily Matter

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

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Purity
>98.0%
Solubility
Soluble in DMSO (10 mm)
Appearance
Pale Yellow Oily Matter
ShelfLife
-20°C 3 years powder; -80°C 2 years in solvent
Storage
Store at 2-8°C
Shipping
Room temperature, or blue ice upon request.
IUPACName
2-[2-[2-[2-(2-aminoethoxy)ethoxy]ethoxy]ethoxy]acetic acid
Synonyms
14-Amino-3,6,9,12-tetraoxatetradecan-1-oic acid; H2N-PEG4-CH2COOH; Amino-PEG4-CH2COOH
Boiling Point
397.6±32.0 °C at 760 mmHg
Density
1.2±0.1 g/cm3
InChI Key
NPRAKTLKDKKZAV-UHFFFAOYSA-N
InChI
InChI=1S/C10H21NO6/c11-1-2-14-3-4-15-5-6-16-7-8-17-9-10(12)13/h1-9,11H2,(H,12,13)
SMILES
C(COCCOCCOCCOCC(=O)O)N

Amino-PEG4-acetic acid, is a polyethylene glycol-based spacer terminating in an amino functionality and a carboxylic acid handle. Its flexible, hydrophilic architecture supports efficient conjugation between recognition and E3-ligase-binding moieties while improving solubility and reducing steric constraints that can impair ternary complex formation. The detailed Structure and Reactivity characteristics are provided below to guide experimental PROTAC assembly.

Structure: Amino-PEG4-acetic acid contains a PEG ether backbone providing conformational flexibility, flanked by an amino group and a terminal acetic acid moiety. The structure features ether linkages along the PEG chain, a primary amine, and a carboxylic acid capable of forming amide or activated ester derivatives. Overall, it is typically water-compatible and conformationally adaptable.

Reactivity: The amino and carboxylic acid functionalities enable standard PROTAC linker coupling strategies. Common approaches include forming amide bonds via carboxyl activation (for example, using carbodiimide coupling reagents with an appropriate base) or converting the acid to reactive esters prior to nucleophilic substitution by amines. Reactions are typically conducted under inert or controlled atmospheres in polar aprotic solvents, with temperature and pH adjusted to preserve sensitive functional groups and minimize side reactions.

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It is commonly abbreviated as: C1V1 = C2V2

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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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