1-Isothiocyanato-PEG3-azide

 CAS No.: 1310686-23-7  Cat No.: BP-501277  Purity: ≥95% 4.5  

1-Isothiocyanato-PEG3-azide is a heterobifunctional polyethylene glycol linker featuring an azide handle and a terminal isothiocyanate electrophile. The PEG3 chain provides aqueous solubility and conformational flexibility, which can reduce steric interference between the two PROTAC modules. In PROTAC construction, the azide group is commonly used for bioorthogonal conjugation (e.g., copper-free azide–alkyne cycloaddition) to attach the linker to an alkyne-functional ligand or payload, enabling modular assembly under mild conditions. In parallel, the isothiocyanate group reacts with primary amines on targeting ligands (such as lysine residues on proteins or amine-bearing small molecules) to form stable thiourea linkages, thereby installing the PEG spacer at the desired position. This linker is valuable for targeted protein degradation research because it supports efficient, site-selective conjugation while maintaining linker length and flexibility that often improve ternary complex formation and degradation performance.

1-Isothiocyanato-PEG3-azide

Structure of 1310686-23-7

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Category
PROTAC Linker
Molecular Formula
C9H16N4O3S
Molecular Weight
260.31
Appearance
Pale Yellow or Colorless Oily Matter

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

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Purity
≥95%
Solubility
Soluble in DMSO
Appearance
Pale Yellow or Colorless Oily Matter
Storage
Store at 2-8°C for short term (days to weeks) or -20°C for long term (months to years)
Shipping
Room temperature in continental US; may vary elsewhere.
IUPACName
1-[2-[2-(2-azidoethoxy)ethoxy]ethoxy]-2-isothiocyanatoethane
Synonyms
1-azido-2-(2-(2-(2-isothiocyanatoethoxy)ethoxy)ethoxy)ethane; 5,8,11-Trioxa-2-azatridec-1-ene, 13-azido-1-thioxo-
InChI Key
WGVGUDRBZOFJRC-UHFFFAOYSA-N
InChI
InChI=1S/C9H16N4O3S/c10-13-12-2-4-15-6-8-16-7-5-14-3-1-11-9-17/h1-8H2
SMILES
C(COCCOCCOCCN=[N+]=[N-])N=C=S

1-Isothiocyanato-PEG3-azide is a PEG-based bifunctional linker designed for modular PROTAC assembly, combining an azide handle for bioorthogonal conjugation with an isothiocyanate group for efficient coupling to nucleophilic residues on targeting ligands. Its flexible, hydrophilic PEG spacer can improve solubility and help tune linker length and conformational freedom in targeted protein degradation workflows. The following sections describe the linker’s structure and practical reactivity considerations in detail.

Structure: This linker contains a polyethylene glycol segment providing conformational flexibility and enhanced aqueous compatibility, terminating in an azide functionality and an isothiocyanate group. The molecule features ether linkages within the PEG backbone and a thiocyanate-derived electrophile suitable for nucleophilic thiourea formation.

Reactivity: PROTAC construction can leverage azide participation in copper-catalyzed azide–alkyne cycloaddition or strain-promoted azide–alkyne chemistry, depending on the partner functional group. The isothiocyanate typically reacts with primary amines or thiols to form stable thiourea or related adducts under mild base-containing conditions. Common solvents include polar aprotic or buffered aqueous mixtures, with careful control of pH and nucleophile concentration to minimize side reactions.

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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

* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
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