Thiol-PEG3-NHBoc

 CAS No.: 1895922-68-5  Cat No.: BP-501449 4.5  

Thiol-PEG3-NHBoc is a heterobifunctional polyethylene glycol linker featuring a terminal thiol for covalent conjugation and a protected amine (NHBoc) for subsequent coupling or controlled deprotection. The PEG3 segment provides a short, flexible hydrophilic spacer that can reduce steric interference and improve the accessibility of functional groups when assembling larger constructs. In PROTAC and targeted protein degradation workflows, this linker is used to connect or functionalize one ligand or reactive handle while maintaining sufficient mobility for productive ternary-complex formation with the target protein and the E3 ligase recruiting element. The thiol enables chemoselective reactions with maleimides, activated disulfides, or other thiol-reactive partners, whereas the Boc-protected nitrogen allows orthogonal coupling strategies under conditions compatible with sensitive biomolecule-binding motifs. Its modular design supports systematic optimization of linker length, attachment chemistry, and overall degradation performance in experimental PROTAC design.

Thiol-PEG3-NHBoc

Structure of 1895922-68-5

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PROTAC Linker
Molecular Formula
C₁₃H₂₇NO₅S
Molecular Weight
309.42

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

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IUPACName
tert-butyl N-[2-[2-[2-(2-sulfanylethoxy)ethoxy]ethoxy]ethyl]carbamate
InChI Key
RWCUSUXTCYNDCV-UHFFFAOYSA-N
InChI
InChI=1S/C13H27NO5S/c1-13(2,3)19-12(15)14-4-5-16-6-7-17-8-9-18-10-11-20/h20H,4-11H2,1-3H3,(H,14,15)
SMILES
CC(C)(C)OC(=O)NCCOCCOCCOCCS

This thiol-terminated PEG-based linker is designed to enable modular construction of PROTACs by providing a chemically addressable handle for conjugation to ligands and subsequent assembly into targeted degradation constructs. Its PEG spacer supports favorable solubility and conformational flexibility, which can improve productive ternary complex formation and overall linker compatibility in PROTAC scaffolds. The following points describe its structure and practical reactivity considerations in detail.

Structure: Thiol-PEG3-NHBoc is a polyethylene glycol spacer bearing a terminal thiol and a protected amine (NHBoc). The molecule contains ether linkages characteristic of PEG, plus a thiofunctional group at one end and a Boc carbamate protecting group at the other. These features support water-compatible behavior and stable handling.

Reactivity: The terminal thiol can be used for thiol–electrophile coupling strategies (for example, maleimide or other thiol-reactive partners) under mild conditions to connect ligands to the linker. The Boc group is typically removed using acid to reveal an amine for subsequent amide or carbamate-forming conjugations. Commonly, reactions are performed in inert or controlled atmospheres with compatible aqueous/organic solvent mixtures to preserve thiol integrity and minimize oxidation; thiol-protecting or reducing conditions may be employed when needed.

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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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