m-PEG4-O-NHS ester

Name: m-PEG4-O-NHS ester
Brand: BOC Sciences
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CAS No.: 147912-03-6

Cat No.: BP-501343 4.5

m-PEG4-O-NHS ester is a mono-functional methoxy-terminated polyethylene glycol linker bearing an activated succinimidyl carbonate for reaction with primary amines. Structurally, it consists of an m-PEG chain of four ethylene glycol units linked to the activated carbonate, providing a flexible, hydrophilic spacer that can be readily conjugated to primary amines on proteins, peptides, or other PROTAC-building blocks. In PROTAC design, this linker serves as a coupling reagent that reacts with an amine-containing ligand to form a carbamate, while the methoxy terminus remains nonreactive. The PEG spacer can improve solubility, reduce nonspecific hydrophobic interactions, and help maintain productive geometry for ternary-complex formation. Its value lies in facilitating controlled synthesis of PEGylated PROTAC intermediates, allowing researchers to tune linker length and polarity while using established activated-carbonate chemistry under mild conditions.

Structure of 147912-03-6

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PROTAC Linker

Molecular Formula

C₁₄H₂₃NO₉

Molecular Weight

349.33

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

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Please store the product under the recommended conditions in the Certificate of Analysis.

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IUPACName

(2,5-dioxopyrrolidin-1-yl) 2-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]ethyl carbonate

InChI Key

UCHQKIQOBVMTDI-UHFFFAOYSA-N

InChI

InChI=1S/C14H23NO9/c1-19-4-5-20-6-7-21-8-9-22-10-11-23-14(18)24-15-12(16)2-3-13(15)17/h2-11H2,1H3

SMILES

COCCOCCOCCOCCOC(=O)ON1C(=O)CCC1=O

This m-PEG4-O-NHS ester is a polyethylene glycol (PEG) based linker designed for efficient conjugation in PROTAC construction. Its succinimidyl carbonate functionality enables robust formation of stable carbamate bonds with primary amines, supporting modular assembly of bifunctional degraders. The PEG segment improves solubility and can help tune linker flexibility, which is often beneficial for productive ternary complex formation. Detailed structural and reactivity considerations are provided below.

Structure: The linker contains a methoxy-terminated PEG chain bearing an activated succinimidyl carbonate at the opposite terminus, enabling coupling to amines. It features carbonate and ether connectivity, contributing to water compatibility and flexible conformational behavior typical of PEG linkers.

Reactivity: The succinimidyl carbonate reacts with primary amines to form carbamate bonds via nucleophilic substitution at the carbonate carbonyl, releasing N-hydroxysuccinimide as the leaving group. Suitable conditions generally involve mild base or buffering to maintain amine nucleophilicity while preventing hydrolysis. Common solvents include polar aprotic media or aqueous-compatible buffers; freshly prepared linker solutions and controlled pH are often used to minimize competing hydrolysis. No specialized catalysts are typically required for this coupling step.

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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