ChemicalBook CAS DataBase List Nε-acryloyl-L-lysin

Nε-acryloyl-L-lysin synthesis

6synthesis methods

Product Name:Nε-acryloyl-L-lysin
CAS Number:48065-82-3
Molecular formula:C9H16N2O3
Molecular Weight:200.23

10098-89-2
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Yield:48065-82-3 92%

Reaction Conditions:

Stage #1: L-Lysine hydrochloridewith copper carbonate hydroxide in water at 101 - 105; for 3 h;
Stage #2: acryloyl chloridewith sodium hydrogencarbonate;sodium hydroxide in water at 0 - 20; pH=8.5 - 9;

Steps:

The monomer LysAAm was synthesized as follows. L-Lysine hydrochloride (5.3 g, 29 mmol) and basic cupric carbonate (4.78 g, 20 mmol) were dissolved in water (50-60 mL) and the system was stirred at 101-105 °C for 3 h. After the insoluble residue was removed by filtration, the pH of the solution was adjusted to 9-9.5 with solid NaHCO3. Then, acryloyl chloride (3.54 mL, 43.5 mmol) was added dropwise into the solution at 0-5 °C and the pH of the mixture was maintained at 8.5-9 by adding 2 M NaOH aqueous solution. After stirring at room temperature for another 12 h, the blue precipitates were filtrated, washed successively with water, methanol and ether, and dried in vacuum. The obtained blue solid (2 g, 4.33 mmol) was dispersed in water (30 mL) in a separation funnel, and a solution of 8-quinolinol (1.89 g, 13 mmol) in chloroform (30 mL) was added. After shaking for 12 h, a green precipitate in the chloroform phase was removed by filtration. Three extractions with chloroform were performed to remove traces of 8-hydroxy quinoline. The aqueous phase was lyophilized, obtaining a white powdered solid. Yield: 92%. The chemical structure of LysAAm was characterized by 1H NMR using D2O as the solvent. 1H NMR (D2O, δ ppm): 1.37 (m, CH2), 1.57 (m, CH2), 1.83 (m, CH2), 3.24 (t, CH2), 3.69 (t, CH), 5.71 (d, CH2=CH [trans]), 6.18 (d, CH2=CH [cis]), 6.21 (dd, CH2=CH).

References:

Cui, Ning;Qian, Junmin;Xu, Weijun;Xu, Minghui;Zhao, Na;Liu, Ting;Wang, Hongjie [Carbohydrate Polymers,2016,vol. 136,p. 1017 - 1026]

38862-24-7 Synthesis