Bromoacetamide-PEG3-C1-acid

 CAS No.: 173323-22-3  Cat No.: BP-501198 4.5  

Bromoacetamide-PEG3-C1-acid is a heterobifunctional PEG-based linker featuring a bromoacetamide electrophile at one end and a terminal carboxylic acid at the other, connected through a short three-unit ethylene glycol spacer. The bromoacetamide group is designed to react with nucleophilic residues such as cysteine thiols or engineered thiol handles via nucleophilic substitution, enabling stable thioether formation under standard PROTAC linker-conjugation workflows. In targeted protein degradation constructs, this linker provides a flexible, hydrophilic separation between the recruitment ligand and the degradation module, helping to reduce steric interference and to tune effective geometry for ternary complex formation. The terminal carboxylic acid further supports downstream coupling strategies (e.g., amide bond formation) to assemble full PROTAC architectures. Overall, it is a useful building block for researchers developing conjugation-ready PROTACs and related targeted degradation probes where controlled spacing and robust covalent linkage are required.

Bromoacetamide-PEG3-C1-acid

Structure of 173323-22-3

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PROTAC Linker
Molecular Formula
C₁₀H₁₈BrNO₆
Molecular Weight
328.16

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

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IUPACName
2-[2-[2-[2-[(2-bromoacetyl)amino]ethoxy]ethoxy]ethoxy]acetic acid
InChI Key
YTQSICXMSXKITM-UHFFFAOYSA-N
InChI
InChI=1S/C10H18BrNO6/c11-7-9(13)12-1-2-16-3-4-17-5-6-18-8-10(14)15/h1-8H2,(H,12,13)(H,14,15)
SMILES
C(COCCOCCOCC(=O)O)NC(=O)CBr

This Bromoacetamide-PEG3-C1-acid linker is designed for efficient incorporation into PROTAC constructs, providing a reactive bromoacetamide handle alongside a PEG-based spacer and a terminal carboxylic acid for controlled conjugation. Its balanced polarity and flexible ether-rich segment support productive ternary-complex formation, while the electrophilic bromoacetamide enables selective formation of stable thioether linkages. The detailed structure and reactivity considerations are provided below.

Structure: The linker contains a bromoacetamide electrophile, an ether-rich PEG spacer, and a terminal carboxylic acid. It features amide and ether functional groups, with an alkyl bromide embedded in the acetamide motif. The PEG segment imparts conformational flexibility and enhanced hydrophilicity.

Reactivity: PROTAC assembly using this linker typically relies on nucleophilic substitution of the bromoacetamide by thiols, forming a stable thioether linkage under mild, aqueous-compatible conditions. Reactions are commonly performed with thiol-bearing ligands or intermediates, using base or buffering systems to promote thiolate formation while minimizing side reactions. Solvent systems such as buffered aqueous media with compatible cosolvents are often used; catalysts are generally not required.

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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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