Description
Propargyl-PEG1-acid is a crosslinker with a propargyl group and a carboxylic acid group. The carboxylic acid reacts with primary amine under the activation of HATU or EDC. The propargyl group can participate in copper catalyzed azide-alkyne Click Chemistry reactions.
Uses
This is a crosslinker with an alkyne group on one end and a carboxyl group on the other end. The alkyne can be used to attach to an azide using copper-catalyzed click chemistry. The compound contains a single PEG unit to help improve solubility.
reaction suitability
reagent type: linker
Synthesis
General procedure for the synthesis of propargyl-monoethylene glycol-carboxylic acid from tert-butyl 3-(prop-2-yn-1-yloxy)propionate: trifluoroacetic acid (8.065 mL, 108.6 mmol) was added to a solution of tert-butyl 3-(prop-2-yn-1-yloxy)propionate (2.0 g, 10.86 mmol) in dichloromethane (50 mL). The reaction mixture was stirred overnight at room temperature and subsequently concentrated under vacuum, co-evaporated with toluene and purified by fast chromatography on 80 g silica gel (using a dichloromethane/methanol gradient elution) to afford 1.1 g of propargyl-monoethyleneglycol-carboxylic acid as an oil (80% yield).1H NMR (400 MHz, DMSO-d6, δ, ppm): 2.46 (t J = 6.4 Hz, 2H); 3.43 (t, J = 2.4 Hz, 1H); 3.63 (t, J = 6.4 Hz, 2H); 4.11 (d, J = 2.4 Hz, 2H); 12.20 (broad peak, 1H).
References
[1] Patent: WO2017/76998, 2017, A1. Location in patent: Page/Page column 222-223
[2] Israel Journal of Chemistry, 2001, vol. 41, # 4, p. 283 - 295
