Azide-PEG3-Tos Chemical Properties

storage temp. 

Storage temp. 2-8°C

solubility 

Soluble in DMSO, DCM, DMF

form 

Liquid

color 

Colorless to light yellow

InChI

InChI=1S/C13H19N3O5S/c1-12-2-4-13(5-3-12)22(17,18)21-11-10-20-9-8-19-7-6-15-16-14/h2-5H,6-11H2,1H3

InChIKey

PTOJCKLTCKYNFG-UHFFFAOYSA-N

SMILES

S(C1C=CC(C)=CC=1)(=O)(=O)OCCOCCOCCN=[N+]=[N-]

Azide-PEG3-Tos Usage And Synthesis

Description

Azide-PEG3-Tos is a heterobifunctional PEG linker.The azide (N3) group is reactive with alkyne, BCN, DBCO via Click Chemistry to yield a stable triazole linkage. Tosyl group is a good leaving group for nucleophilic substitution reactions.

Uses

Azide-PEG3-Tos is a PEG-based PROTAC linker that can be used in the synthesis of PROTACs[1]. Azide-PEG3-Tos is also a non-cleavable 3 unit PEG ADC linker used in the synthesis of antibody-drug conjugates (ADCs)[2]. Azide-PEG3-Tos is a click chemistry reagent, it contains an Azide group and can undergo copper-catalyzed azide-alkyne cycloaddition reaction (CuAAc) with molecules containing Alkyne groups. It can also undergo strain-promoted alkyne-azide cycloaddition (SPAAC) reactions with molecules containing DBCO or BCN groups.

IC 50

PEGs; Non-cleavable Linker

References

[1] Borchmann DE, et al. GRGDS-Functionalized Poly(lactide)-graft-poly(ethylene glycol) Copolymers: Combining Thiol-Ene Chemistry with Staudinger Ligation. Macromolecules. 2013 Jun 11;46(11):4426-4431. DOI:10.1021/ma4005633
[2] Park, Tae Kyo, et al. Compound bearing beta-galactoside-introduced self-immolative linker. WO2018124758A2.

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