Thiol-PEG3-Boc

 CAS No.: 1446282-39-8  Cat No.: BP-500839 4.5  

Thiol-PEG3-Boc is a heterobifunctional PEG linker featuring a free thiol group at one terminus and a Boc-protected carboxylate at the other, connected through a triethylene glycol spacer. The unprotected thiol provides a potent nucleophilic handle for chemoselective bioconjugation with maleimide-, haloacetamide-, or pyridyl disulfide-functionalized ligands, forming stable thioether or disulfide linkages under mild physiological conditions. This thiol-based conjugation chemistry is widely employed in PROTAC assembly due to its high selectivity and compatibility with aqueous conditions, enabling site-specific attachment of target protein-binding warheads or E3 ubiquitin ligase-recruiting moieties that bear appropriate electrophilic or disulfide-reactive groups. The Boc group protects the distal carboxylic acid during thiol-mediated conjugation and can be removed under standard acidic conditions to reveal a free carboxylate for subsequent amide coupling with amine-containing ligands. The PEG spacer enhances aqueous solubility and provides the conformational flexibility necessary for productive ternary complex formation. Researchers utilize this linker to leverage thiol-selective conjugation chemistry in PROTAC design, investigating how the resulting thioether or disulfide linkages influence degradation potency, metabolic stability, and the overall physicochemical properties of PROTAC molecules in targeted protein degradation studies.

Thiol-PEG3-Boc

Structure of 1446282-39-8

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PROTAC Linker
Molecular Formula
C₁₃H₂₆O₅S
Molecular Weight
294.41

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

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Please store the product under the recommended conditions in the Certificate of Analysis.
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IUPACName
tert-butyl 3-[2-[2-(2-sulfanylethoxy)ethoxy]ethoxy]propanoate
Synonyms
Thiol-PEG3-t-butyl ester
InChI Key
JLMCOVSNILLDKP-UHFFFAOYSA-N
InChI
InChI=1S/C13H26O5S/c1-13(2,3)18-12(14)4-5-15-6-7-16-8-9-17-10-11-19/h19H,4-11H2,1-3H3
SMILES
CC(C)(C)OC(=O)CCOCCOCCOCCS

Thiol-PEG3-Boc, also referred to as Thiol-PEG3-t-butyl ester, is a bifunctional PEG linker containing a free thiol and a tert-butyl-protected carboxyl group. Its short PEG spacer provides a flexible, polar connection between conjugated components, while the independently addressable thiol and protected acid support stepwise assembly of PROTACs and related conjugates.

Structure: Thiol-PEG3-Boc contains a PEG3-based chain with a free terminal thiol and a carboxylic acid masked as a tert-butyl ester. The “Boc” designation in the product name refers to the tert-butyl ester-protected carboxyl terminus; it does not indicate a Boc-protected thiol or amine. Ether linkages within the PEG segment contribute polarity and conformational flexibility.

Reactivity: The free thiol is available for direct coupling with maleimides, vinyl sulfones, haloalkyl reagents, and other thiol-reactive electrophiles. Acid-mediated cleavage of the tert-butyl ester exposes the corresponding carboxylic acid rather than liberating the thiol. The resulting acid can be activated for subsequent amide or ester formation. Controlled handling and, where appropriate, an oxygen-limited atmosphere can help reduce unwanted thiol oxidation during synthesis and storage.

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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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Historical Records: Phthalimide-PEG4-MPDM-OH | Benzyl-PEG7-Ms | endo-BCN-PEG6-Boc | Tr-PEG2-OH | Methylamino-PEG7-benzyl | Benzyl-PEG7-t-butyl ester | Hydroxy-PEG5-acid | Mal-PEG2-COOtBu | Amino-PEG36-CONH-PEG36-acid | Thiol-PEG5-propionic acid | Thiol-PEG3-Boc

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