Thiol-C9-PEG5

 CAS No.: 130727-42-3  Cat No.: BP-501074 4.5  

Thiol-C9-PEG5 is a heterobifunctional PROTAC linker building block featuring a terminal thiol for site-specific conjugation and an extended polyethylene glycol (PEG) spacer that provides aqueous solubility and conformational flexibility. The “C9” segment denotes a hydrophobic aliphatic chain length that can tune the effective distance and orientation between the two PROTAC-relevant moieties, while the PEG5 portion (five ethylene glycol units) helps reduce nonspecific hydrophobic interactions and can improve overall bioconjugate stability. In PROTAC design, such linkers are used to connect a ligand for an E3 ubiquitin ligase to a target-binding warhead through controlled spacing, thereby facilitating formation of a productive ternary complex and promoting ubiquitination and subsequent proteasomal degradation. This product is valuable for researchers optimizing linker length and polarity to balance potency, selectivity, and synthesis feasibility in targeted protein degradation workflows.

Thiol-C9-PEG5

Structure of 130727-42-3

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PROTAC Linker
Molecular Formula
C₁₉H₄₀O₅S
Molecular Weight
380.58

* 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
2-[2-[2-[2-(11-sulfanylundecoxy)ethoxy]ethoxy]ethoxy]ethanol
InChI Key
IOBMVUDHPRVCSO-UHFFFAOYSA-N
InChI
InChI=1S/C19H40O5S/c20-10-12-22-14-16-24-18-17-23-15-13-21-11-8-6-4-2-1-3-5-7-9-19-25/h20,25H,1-19H2
SMILES
C(CCCCCOCCOCCOCCOCCO)CCCCCS

Thiols are widely used as versatile handles for constructing PROTAC conjugates, and Thiol-C9-PEG5 provides a PEG-based, flexible linker platform that can be readily functionalized and coupled to ligands. Its ether-rich scaffold supports solubility and conformational adaptability, which can improve productive ternary complex formation in targeted protein degradation workflows. The structure and reactivity considerations for assembling PROTACs using this linker are described in detail below.

Structure: Thiol-C9-PEG5 is a PEGylated linker featuring an aliphatic spacer terminating in a reactive thiol, with multiple ether linkages that impart flexibility and hydrophilicity. The molecule contains C–S and C–O bonds, with a terminal sulfur functionality suitable for selective derivatization under mild conditions.

Reactivity: The terminal thiol enables formation of thioether or thiol-reactive intermediates via nucleophilic substitution or thiol–electrophile coupling, commonly using activated haloacetyl, maleimide, or other electrophilic partners used in bioconjugation. Typically, reactions are performed under inert atmosphere or controlled oxygen conditions to minimize thiol oxidation, using aqueous/organic compatible buffers and base or pH control as appropriate for the chosen electrophile.

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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

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g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
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