Thiol-PEG2-t-butyl ester

Name: Thiol-PEG2-t-butyl ester
Brand: BOC Sciences
Rating: 5 (1 reviews)

CAS No.: 1398044-50-2

Cat No.: BP-501309

Purity: >95% 4.5

Thiol-PEG2-t-butyl ester is a short, thiol-bearing polyethylene glycol linker featuring a terminal protected carboxyl group as a tert-butyl ester and a PEG chain length of two ethylene glycol units. Structurally, it provides a flexible hydrophilic spacer that can improve solubility and reduce steric constraints when conjugated to PROTAC components. In targeted protein degradation design, the linker’s thiol handle enables site-selective coupling to electrophilic groups on ligands (e.g., via maleimide or activated ester chemistry), while the tert-butyl ester can be used as a protected carboxyl functionality during synthesis and later deprotected to yield a reactive acid for subsequent amide or ester formation. This combination supports modular assembly of bifunctional degraders, allowing researchers to tune spatial arrangement between the E3 ligase-recruiting moiety and the target-binding ligand, which is critical for productive ternary complex formation and degradation efficiency.

Structure of 1398044-50-2

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Category

PROTAC Linker

Molecular Formula

C₁₁H₂₂O₄S

Molecular Weight

250.35

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

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Purity

>95%

Storage

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

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Room temperature in continental US; may vary elsewhere.

IUPACName

tert-butyl 3-[2-(2-sulfanylethoxy)ethoxy]propanoate

Synonyms

HS-PEG2-CH2CH2COOtBu; tert-butyl 3-[2-(2-sulfanylethoxy)ethoxy]propanoate

Boiling Point

330.6±27.0 °C at 760 mmHg

Density

1.0±0.1 g/cm3

InChI Key

WUDGYPDPSZWMNE-UHFFFAOYSA-N

InChI

InChI=1S/C11H22O4S/c1-11(2,3)15-10(12)4-5-13-6-7-14-8-9-16/h16H,4-9H2,1-3H3

SMILES

CC(C)(C)OC(=O)CCOCCOCCS

Thiol-PEG2-t-butyl ester is a polyethylene glycol-based PROTAC linker designed to enable efficient conjugation between targeting ligands and E3-recruiting modules while maintaining favorable solubility and conformational flexibility. Its free thiol supports thiol-selective coupling, while the tert-butyl ester protects a carboxylic acid for controlled assembly workflows. The detailed Structure and Reactivity parameters for PROTAC construction are provided below.

Structure: The linker comprises a short PEG segment bearing a free thiol and a carboxylic acid protected as a tert-butyl ester, providing orthogonal reactive handles. It contains ether linkages within the PEG chain, a free thiol, and a tert-butyl ester protecting a carboxylic acid.

Reactivity: PROTAC synthesis can use the free thiol directly for thiol-selective ligation, while acid-mediated removal of the tert-butyl ester reveals the corresponding carboxylic acid for separate coupling. Suitable transformations include amide formation, thioester/thioether-forming conjugations, or thiol-based ligation strategies, depending on partner chemistry. Common approaches use mild organic solvents with controlled temperature and acid/base workups; catalysts are chosen to match the specific coupling chemistry while minimizing thiol oxidation.

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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