Boc-PEG2-sulfonic acid

 CAS No.: 1817735-40-2  Cat No.: BP-501164 4.5  

Boc-PEG2-sulfonic acid is a polyethylene glycol–based linker building block featuring a terminal sulfonic acid functionality and a tert-butyl ester-protected carboxylic acid, providing a chemically versatile, water-compatible spacer for PROTAC synthesis. Structurally, the short PEG chain confers conformational flexibility and improves solubility, while the sulfonic acid mainly contributes strong acidity and water solubility rather than serving as a standard covalent-coupling handle. In PROTAC design, such PEG–sulfonate linkers help position the two ligands at an optimal distance and orientation to facilitate formation of the ternary complex and subsequent ubiquitination-driven degradation. The tert-butyl ester protects the carboxylic acid during multi-component assembly and can be removed before subsequent coupling, reducing side reactions and simplifying purification workflows. As a practical linker reagent, it supports systematic variation of linker properties to optimize degradation potency and cooperativity in targeted protein degradation experiments.

Boc-PEG2-sulfonic acid

Structure of 1817735-40-2

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Category
PROTAC Linker
Molecular Formula
C₁₁H₂₂O₇S
Molecular Weight
298.35

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

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IUPACName
2-[2-[3-[(2-methylpropan-2-yl)oxy]-3-oxopropoxy]ethoxy]ethanesulfonic acid
InChI Key
HBIDYLRBESNRPU-UHFFFAOYSA-N
InChI
InChI=1S/C11H22O7S/c1-11(2,3)18-10(12)4-5-16-6-7-17-8-9-19(13,14)15/h4-9H2,1-3H3,(H,13,14,15)
SMILES
CC(C)(C)OC(=O)CCOCCOCCS(=O)(=O)O

Boc-PEG2-sulfonic acid is a PEG-based, sulfonic-acid-bearing linker building block designed to support PROTAC assembly by providing hydrophilic spacing and a chemically addressable functional handle. Its tert-butyl ester-protected carboxyl functionality enables controlled coupling strategies, while the sulfonate group supports robust aqueous compatibility and stable linker incorporation. The molecule is therefore well suited for constructing targeted protein degraders, and the following sections describe its structure and practical reactivity considerations in PROTAC workflows.

Structure: The linker combines a tert-butyl ester-protected carboxylic acid with a short poly(ethylene glycol) segment and a sulfonic acid functionality. It contains ether linkages within the PEG chain, a tert-butyl ester protecting group, and strongly polar sulfonate-associated bonding that enhances water compatibility.

Reactivity: The tert-butyl ester enables orthogonal synthesis: deprotection under acidic conditions reveals a carboxylic acid for subsequent amide-forming coupling. The sulfonic acid group can be retained during coupling to maintain solubility, or converted to activated derivatives when needed for further conjugation. Typical PROTAC linker assembly employs carbodiimide-based coupling for amide bond formation, with polar aprotic solvents and temperature-controlled conditions to preserve sensitive partners.

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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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