t-Boc-N-amido-PEG4-propionic acid

 CAS No.: 756525-91-4  Cat No.: BP-501723  Purity: ≥95% 4.5  

t-Boc-N-amido-PEG4-propionic acid is a PEG-based, amide-functional linker building block designed for PROTAC synthesis. Structurally, it comprises a four-unit ethylene glycol (PEG4) spacer that provides aqueous solubility and conformational flexibility, terminated on one side by a protected N-amide (t-Boc) and on the other by a propionic acid suitable for coupling. In PROTAC architectures, PEG linkers are widely used to tune the effective distance and relative orientation between the ligand-binding “warhead” and the recruitment module, thereby improving productive ternary complex formation and degradation efficiency. The amide and carboxylic acid functionalities enable robust stepwise conjugation under standard peptide/amide coupling conditions, while the t-Boc group supports controlled protection during multi-component assembly. This linker is valuable for researchers seeking to systematically vary linker length and hydrophilicity to optimize targeted protein degradation workflows and structure–activity relationships.

t-Boc-N-amido-PEG4-propionic acid

Structure of 756525-91-4

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Category
PROTAC Linker
Molecular Formula
C16H31NO8
Molecular Weight
365.42
Related CAS
187848-68-6 (polymer)
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 DMSO (10 mm)
Appearance
Pale Yellow or Colorless Oily Matter
Storage
Store at 2-8°C
Shipping
Room temperature, or blue ice upon request.
IUPACName
3-[2-[2-[2-[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethoxy]ethoxy]ethoxy]ethoxy]propanoic acid
Synonyms
t-Boc-N-amido-PEG4-acid; 15-(Boc-amino)-4,7,10,13-tetraoxapentadecanoic acid; 2,2-Dimethyl-4-oxo-3,8,11,14,17-pentaoxa-5-azaicosan-20-oic acid; (Boc-amino)-PEG4-carboxylic Acid; Boc-NH-PEG4-CH2CH2COOH; t-Boc-NH-amido-PEG4-COOH; Boc-NH-PEG4-COOH; N-(tert-Butyloxycarbonyl)-15-amino-4,7,10,13-tetraoxapentanedecanoic Acid; 5,8,11,14-Tetraoxa-2-azaheptadecanedioic acid, 1-(1,1-dimethylethyl) ester
Boiling Point
504.5±50.0 °C at 760 mmHg
Density
1.124±0.06 g/cm3 at 20°C, 760 Torr
InChI Key
YEIYIPDFZMLJQH-UHFFFAOYSA-N
InChI
InChI=1S/C16H31NO8/c1-16(2,3)25-15(20)17-5-7-22-9-11-24-13-12-23-10-8-21-6-4-14(18)19/h4-13H2,1-3H3,(H,17,20)(H,18,19)
SMILES
CC(C)(C)OC(=O)NCCOCCOCCOCCOCCC(=O)O
Biological Activity
Boc-NH-PEG4-CH2CH2COOH is a PEG-based PROTAC linker can be used in the synthesis of PROTAC[1]. Boc-NH-PEG4- CH2CH2COOH is also a cleavable ADC linker used as a linker for antibody-drug conjugates (ADC)[2] . In Vitro: PROTACs contain two different ligands connected by a linker; one is a ligand for an E3 ubiquitin ligase and the other is for the target protein. PROTACs exploit the intracellular ubiquitin-proteasome system to selectively degrade target proteins. ADC linker used in the synthesis of antibody-drug conjugates (ADCs)

t-Boc-N-amido-PEG4-propionic acid, provides a PEG-based, amide-containing spacer that supports controlled spatial separation between targeting and recruiting ligands. Its protected carboxyl functionality and amide linkage enable modular synthesis of degraders, improving conjugation flexibility and often enhancing solubility and linker processability in PROTAC workflows. The detailed Structure and Reactivity parameters are provided below.

Structure: The molecule contains a poly(ethylene glycol) chain that confers hydrophilicity and conformational flexibility, terminated by a propionic acid motif. An amide linkage connects the PEG segment to the carbonyl framework, while a t-Boc group provides acid/base-stable protection for downstream coupling chemistry.

Reactivity: The protected carboxylic acid and t-Boc group are designed for stepwise PROTAC assembly. Deprotection under standard Boc-removal conditions generates a free amine or carboxyl handle (depending on synthetic design), enabling amide or ester-forming coupling to ligand scaffolds. Common coupling strategies employ activated carboxylic acids (e.g., carbodiimide or uronium-type reagents) in polar aprotic solvents, with base to promote nucleophilic acyl substitution.

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* 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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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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