m-PEG8-succinimidyl carbonate

 CAS No.: 1372860-04-2  Cat No.: BP-501301 4.5  

m-PEG8-succinimidyl carbonate is a monofunctional methoxy-PEG linker bearing an activated succinimidyl carbonate at the reactive end, providing a stable, water-soluble spacer and a reactive amine-targeting group. The PEG segment (approximately eight ethylene glycol units) confers flexibility and reduces steric interference, while the succinimidyl carbonate undergoes chemoselective acyl transfer with primary amines on lysine residues or N-terminal groups to form a stable carbamate linkage. In PROTAC design, this linker is used to conjugate one ligand or functional moiety to an amine-bearing partner, enabling controlled spatial presentation of the binding elements to the target protein and the E3 ligase recruiter. Its PEG-mediated solubility and distance control can improve conjugate handling, limit nonspecific aggregation, and support reproducible synthesis of targeted protein degradation constructs for mechanistic and optimization studies.

m-PEG8-succinimidyl carbonate

Structure of 1372860-04-2

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PROTAC Linker
Molecular Formula
C₂₂H₃₉NO₁₃
Molecular Weight
525.54

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

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IUPACName
(2,5-dioxopyrrolidin-1-yl) 2-[2-[2-[2-[2-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethyl carbonate
InChI Key
KGBOFEYHJAHPNI-UHFFFAOYSA-N
InChI
InChI=1S/C22H39NO13/c1-27-4-5-28-6-7-29-8-9-30-10-11-31-12-13-32-14-15-33-16-17-34-18-19-35-22(26)36-23-20(24)2-3-21(23)25/h2-19H2,1H3
SMILES
COCCOCCOCCOCCOCCOCCOCCOCCOC(=O)ON1C(=O)CCC1=O

m-PEG8-succinimidyl carbonate is a PEG-based linker designed for efficient conjugation of targeting ligands in PROTAC architectures. Its succinimidyl carbonate functionality enables robust formation of stable carbamate linkages under standard bioconjugation conditions, supporting reliable assembly of degraders that rely on precise spatial presentation of binding moieties. The subsequent points describe the linker’s structure and practical reactivity considerations in detail.

Structure: The linker comprises a methoxy-terminated polyethylene glycol chain connected to a succinimidyl carbonate group. It contains PEG ether linkages and a carbonate motif bearing an N-hydroxysuccinimide leaving group, providing a flexible, hydrophilic scaffold that supports solubility and controlled linker length in conjugates.

Reactivity: The succinimidyl carbonate reacts with primary amines to form carbamate bonds via nucleophilic acyl substitution, releasing N-hydroxysuccinimide. Suitable conditions typically employ aqueous buffers with controlled pH to maintain amine nucleophilicity while preserving reagent stability. Commonly used solvents include water or water-organic mixtures, and reactions are often performed at mild temperature with inert atmosphere when required to minimize hydrolysis.

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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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