Tos-PEG3-C2-methyl ester

 CAS No.: 1239588-09-0  Cat No.: BP-501376 4.5  

Tos-PEG3-C2-methyl ester is a PEG-based PROTAC linker featuring a tosyl (tosylate) capping group and a short, three–ethylene glycol unit chain terminated with a methyl ester at the C2 position. Structurally, it provides a flexible, water-compatible spacer that can be incorporated between a ligand and an electrophilic handle for subsequent conjugation. In PROTAC design, the linker’s primary role is to tune the spatial relationship and effective reach between the target-binding moiety and the E3 ligase recruiter, thereby improving productive ternary complex formation and degradation efficiency. The tosylate functionality is commonly used as a reactive leaving group for nucleophilic substitution or controlled derivatization, while the methyl ester offers a handle for further chemical modification (e.g., conversion to other carboxylate-reactive forms) depending on the coupling strategy. This product is valuable for researchers seeking modular, chemically tractable linker scaffolds to rapidly prototype and optimize targeted protein degradation constructs.

Tos-PEG3-C2-methyl ester

Structure of 1239588-09-0

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PROTAC Linker
Molecular Formula
C₁₇H₂₆O₈S
Molecular Weight
390.45

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

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IUPACName
methyl 3-[2-[2-[2-(4-methylphenyl)sulfonyloxyethoxy]ethoxy]ethoxy]propanoate
InChI Key
YHLPCWBPMJZTKG-UHFFFAOYSA-N
InChI
InChI=1S/C17H26O8S/c1-15-3-5-16(6-4-15)26(19,20)25-14-13-24-12-11-23-10-9-22-8-7-17(18)21-2/h3-6H,7-14H2,1-2H3
SMILES
CC1=CC=C(C=C1)S(=O)(=O)OCCOCCOCCOCCC(=O)OC

Tos-PEG3-C2-methyl ester is a polyethylene glycol-based PROTAC linker building block designed to connect ligands while providing conformational flexibility and improved solubility in typical conjugation solvents. Its ester functionality enables efficient, modular installation into larger targeted protein degradation constructs. The linker’s design supports robust synthetic assembly of bifunctional degraders, and the sections below describe its structural features and practical reactivity considerations in detail.

Structure: The material combines a tosyl-activated PEG segment with a terminal methyl ester and an ethyl-like spacer motif. It contains ether linkages along the PEG chain, aromatic sulfonyl functionality, and an ester carbonyl, providing a polar, flexible scaffold with enhanced hydrophilicity.

Reactivity: The methyl ester and tosyl-activated handle make the linker suitable for stepwise PROTAC synthesis via nucleophilic acyl substitution or related coupling strategies, depending on the partner functional group. Typical approaches employ mild base or nucleophile activation in polar aprotic solvents, with temperature and stoichiometry tuned to minimize hydrolysis. Reaction monitoring is commonly performed by analytical chromatography or spectroscopy to confirm selective conversion and preserve linker integrity.

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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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g/mol
Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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