t-Boc-N-amido-PEG6-propionic acid

 CAS No.: 882847-13-4  Cat No.: BP-500470  Purity: ≥95% 4.5  

t-Boc-N-amido-PEG6-propionic acid is a PEG-based linker building block incorporating a terminal propionic acid functionality and a protected amide/urethane handle (t-Boc) for controlled coupling chemistry. Structurally, it provides a flexible, hydrophilic polyethylene glycol chain of moderate length that can reduce steric congestion and improve aqueous solubility when appended to PROTAC constructs. In targeted protein degradation workflows, this linker is used to spatially separate a ligand-bearing moiety from the remainder of the degrader scaffold, enabling productive formation of the ternary complex by maintaining favorable relative orientation and minimizing unfavorable intramolecular interactions. The terminal carboxylic acid supports amide or ester bond formation to install the linker onto other PROTAC components, while the t-Boc-protected group can be deprotected and subsequently functionalized for sequential synthesis. As a modular PEG linker, it is valuable for optimizing linker length and attachment points to tune degradation potency, selectivity, and physicochemical properties in structure–activity studies.

t-Boc-N-amido-PEG6-propionic acid

Structure of 882847-13-4

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Category
PROTAC Linker
Molecular Formula
C20H39NO10
Molecular Weight
453.52
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 -20°C, keep in dry and avoid sunlight
Shipping
Room temperature
IUPACName
3-[2-[2-[2-[2-[2-[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]propanoic acid
Synonyms
Boc-NH-PEG6-CH2CH2COOH; t-Boc-NH-amido-PEG6-COOH; Boc-NH-PEG6-COOH; t-Boc-N-amido-PEG6-acid; Boc-21-amino-4,7,10,13,16,19-hexaoxaheneicosanoic acid; 21-(Boc-amino)-4,7,10,13,16,19-hexaoxaheneicosanoic acid; 2,2-Dimethyl-4-oxo-3,8,11,14,17,20,23-heptaoxa-5-azahexacosan-26-oic acid; 3,8,11,14,17,20,23-Heptaoxa-5-azahexacosan-26-oic acid, 2,2-dimethyl-4-oxo-; 21-[(tert-Butoxycarbonyl)amino]-4,7,10,13,16,19-hexaoxaheneicosanoic Acid; 5,8,11,14,17,20-Hexaoxa-2-azatricosanedioic acid 1-(1,1-dimethylethyl) ester
Boiling Point
568.1±50.0 °C at 760 mmHg
Density
1.123±0.06 g/cm3
InChI Key
FTTYOIHYERRXQB-UHFFFAOYSA-N
InChI
InChI=1S/C20H39NO10/c1-20(2,3)31-19(24)21-5-7-26-9-11-28-13-15-30-17-16-29-14-12-27-10-8-25-6-4-18(22)23/h4-17H2,1-3H3,(H,21,24)(H,22,23)
SMILES
CC(C)(C)OC(=O)NCCOCCOCCOCCOCCOCCOCCC(=O)O

t-Boc-N-amido-PEG6-propionic acid, provides a polyethylene glycol spacer with a protected amide handle and a carboxylic acid for controlled conjugation. Its hydrophilic, flexible architecture supports favorable solubility and reduced steric bias in bifunctional degraders. The Boc-protected functionality enables stepwise assembly of PROTACs, facilitating reliable coupling to targeting ligands and E3-recruiting moieties. Detailed structural and synthetic considerations are provided below.

Structure: The linker contains a PEG-based polyether chain that confers conformational flexibility and hydrophilicity, flanked by an amide linkage and a terminal carboxylic acid. A Boc-protected nitrogen and amide carbonyl establish stable covalent connectivity, while ether oxygen atoms support hydrogen-bonding interactions.

Reactivity: The carboxylic acid can be activated for amide-bond formation using standard coupling chemistries, typically via carbodiimide or uronium-type activators with a base in polar aprotic solvents. The Boc group is removable under controlled acid conditions to reveal an amine for subsequent coupling. These steps enable modular PROTAC synthesis through sequential deprotection and bond formation, with purification by conventional chromatography or precipitation where appropriate.

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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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