Description
Amino-PEG3-azide is a bifunctional PEG linker containing an amino group and an azide group. The hydrophilic PEG spacer increases solubility in aqueous media. The amino group is reactive with carboxylic acids, activated NHS esters, carbonyls (ketone, aldehyde) etc. The azide group can react with alkyne, BCN, DBCO via Click Chemistry to yield a stable triazole linkage.
Chemical Properties
Very Pale Yellow Oil
Uses
11-Azido-3,6,9-trioxaundecan-1-amine is an azide with polyethylene glycol-like characteristics that can be used to prepare azide-functionalized polymers via click reaction.
Uses
A PEG derivative, which contains a free amine that can be conjugated to biological molecules directly by an amide linkage (or via the corresponding isothiocyanate) and an azide that can be reduced to an amine for conjugation to other molecules.
PEG derivatives are water soluble. Bifunctional water soluble compounds with flexible dimensions allow for conjugation of small molecules to proteins or molecular probes. 1-amino-11-azido-3,6,9-trioxaundecane can be reacted with small organic molecules for the synthesis of heterobifunctional compounds. It has been used to synthesize a mannose-fluorescein conjugate for the study of cell-surface mannose-specific lectins.
reaction suitability
reaction type: click chemistry
reagent type: cross-linking reagent
Synthesis
In a dry reactor, hydrazine monohydrate (0.95 mL, 19.5 mmol) was added to a solution of TEG-azide (1.7 g, 4.9 mmol) dissolved in (40 mL) under a nitrogen atmosphere. The reaction mixture was then heated and stirred under reflux for 18 hours. At the end of the reaction the reaction mixture was cooled to room temperature and the white precipitate produced in the reaction system was removed by filtration. The resulting filtrate was concentrated under reduced pressure to remove the organic solvent. The residue was then stirred in ether (20 ml) for 1 h. The product was obtained by filtering the organic matter and concentrating the filtrate under reduced pressure.
