Ms-PEG8-Boc

 CAS No.: 2097604-01-6  Cat No.: BP-500956 4.5  

Ms-PEG8-Boc is a heterobifunctional PEG linker featuring a methanesulfonyl (mesyl) leaving group at one terminus and a Boc-protected carboxylate at the other, connected through an extended octaethylene glycol spacer. The mesyl group serves as an efficient leaving group for nucleophilic substitution reactions, enabling conjugation to nucleophile-bearing ligands such as those containing free thiols, amines, or alcohols under mild conditions. This reactivity is particularly valuable in PROTAC synthesis for attaching target protein-binding warheads or E3 ubiquitin ligase-recruiting moieties that present suitable nucleophilic functional groups. The mesylate offers kinetic advantages over bulkier sulfonate alternatives, often providing higher conjugation yields with precious ligands. The Boc group protects the distal carboxylic acid during nucleophilic substitution and can be removed under standard acidic conditions to reveal a free carboxylate for subsequent amide coupling. The extended PEG chain confers substantial aqueous solubility and conformational flexibility, critical for bridging the spatial gap required for productive ternary complex formation. Researchers employ this linker to leverage nucleophilic substitution chemistry in PROTAC assembly, investigating how extended PEG spacer lengths and mesylate-mediated conjugation influence degradation efficiency in targeted protein degradation studies.

Ms-PEG8-Boc

Structure of 2097604-01-6

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PROTAC Linker
Molecular Formula
C₂₄H₄₈O₁₃S
Molecular Weight
576.70

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

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IUPACName
tert-butyl 3-[2-[2-[2-[2-[2-[2-[2-(2-methylsulfonyloxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]propanoate
InChI Key
ARFPSYCSFDJABG-UHFFFAOYSA-N
InChI
InChI=1S/C24H48O13S/c1-24(2,3)37-23(25)5-6-28-7-8-29-9-10-30-11-12-31-13-14-32-15-16-33-17-18-34-19-20-35-21-22-36-38(4,26)27/h5-22H2,1-4H3
SMILES
CC(C)(C)OC(=O)CCOCCOCCOCCOCCOCCOCCOCCOCCOS(=O)(=O)C

This heterofunctional oligoether linker precursor combines a mesylate electrophile with an acid-labile protected carboxyl group. It enables nucleophilic attachment at one terminus and later amidation at the other, supporting directional assembly of flexible PROTAC linkers. Its properties are detailed below.

Structure: An extended oligoether chain terminates in a methanesulfonate and a tert-butyl propanoate. Numerous ether bonds provide conformational freedom, while the sulfonate ester supplies an electrophilic carbon bearing an effective leaving group and the ester masks a terminal carboxylic acid.

Reactivity: Displace the mesylate with an amine, thiolate, phenoxide, or azide through bimolecular nucleophilic substitution in anhydrous dimethylformamide, acetonitrile, or another polar aprotic solvent; a nonnucleophilic base may be used when appropriate. Acidic cleavage of the tert-butyl ester subsequently reveals a carboxyl group for carbodiimide- or uronium-mediated amidation with an amine-bearing PROTAC component.

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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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