Cbz-N-amido-PEG3-acid

 CAS No.: 1310327-18-4  Cat No.: BP-501101  Purity: >98% 4.5  

Cbz-N-amido-PEG3-acid is a polyethylene glycol–based PROTAC linker building block featuring a terminal carboxylic acid for coupling and a PEG3 spacer that provides aqueous solubility and conformational flexibility. The Cbz-protected amide functionality enables controlled amide formation with targeting ligands or warhead moieties under standard peptide/amide coupling conditions, while the short PEG chain helps reduce steric interference at the ternary-complex interface. In PROTAC architectures, such PEG linkers are commonly used to tune the effective distance and relative orientation between the ligand that recruits an E3 ligase and the ligand that binds the target protein, thereby improving productive engagement and degradation efficiency. This linker is valuable for constructing modular, chemically defined conjugates for targeted protein degradation studies, facilitating systematic structure–activity relationship exploration by varying attachment points and linker length while maintaining compatibility with aqueous experimental workflows.

Cbz-N-amido-PEG3-acid

Structure of 1310327-18-4

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Category
PROTAC Linker
Molecular Formula
C₁₇H₂₅NO₇
Molecular Weight
355.38
Appearance
Viscous Liquid

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

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Purity
>98%
Appearance
Viscous Liquid
Storage
Please store the product under the recommended conditions in the Certificate of Analysis.
Shipping
Room temperature in continental US; may vary elsewhere.
IUPACName
3-[2-[2-[2-(phenylmethoxycarbonylamino)ethoxy]ethoxy]ethoxy]propanoic acid
Synonyms
Cbz-12-amino-4,7,10-trioxadodecanoic acid; CBZ-AEEEP; Cbz-NH-PEG3-CH2CH2COOH; Cbz-NH-PEG3-propionic acid
InChI Key
SBHUTZVKPJPFBD-UHFFFAOYSA-N
InChI
InChI=1S/C17H25NO7/c19-16(20)6-8-22-10-12-24-13-11-23-9-7-18-17(21)25-14-15-4-2-1-3-5-15/h1-5H,6-14H2,(H,18,21)(H,19,20)
SMILES
C1=CC=C(C=C1)COC(=O)NCCOCCOCCOCCC(=O)O

Cbz-N-amido-PEG3-acid (also referred to as Cbz-N-amido-PEG3-carboxylic acid), provides a polyethylene glycol–based spacer terminating in a carboxylic acid for versatile conjugation. Its ether-rich backbone supports conformational flexibility and aqueous compatibility, while the Cbz-protected amide functionality enables controlled coupling strategies. These features make it well suited for assembling bifunctional degraders where precise linker geometry and reliable amide bond formation are critical; detailed structural and synthetic considerations are provided below.

Structure: The linker contains a PEG-derived polyether chain with an amide linkage and a terminal carboxylic acid, plus a benzyloxycarbonyl (Cbz) protecting group on the nitrogen. It features multiple ether oxygen atoms, an amide carbonyl, and a carboxylic acid capable of hydrogen bonding and salt formation.

Reactivity: The carboxylic acid can be activated for amide coupling using standard peptide-coupling chemistries, typically via carboxylate activation followed by nucleophilic attack by an amine-bearing partner. The Cbz group supports orthogonal protection, allowing selective deprotection under hydrogenolysis conditions when required, without disturbing the PEG backbone. Common solvents include polar aprotic media compatible with coupling reagents, and reaction temperatures are chosen to maintain linker integrity 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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