3-CHLORO-L-ALANINE HYDROCHLORIDE

• as a substrate for screening tyrosine phenol lyase steady state kinetics
• in the inhibition of serine palmitoyltransferase and cytotoxicity studies in lymphocyte Ly-1 cells
• as an inhibitor of alanine transaminase in wheat germ cell-free protein synthesis system

16428-75-4

51887-89-9

General procedure for the synthesis of 3-chloro-L-alanine hydrochloride from L-serine hydrochloride: L-serine hydrochloride (100 g, 0.7067 mol) was suspended in 500 ml of tetrahydrofuran, and the temperature of the reaction was controlled to be lower than 50 °C, and thionyl chloride (101 g, 0.8480 mol) was added dropwise slowly. After the dropwise addition, the temperature was gradually increased to 50 °C and the reaction was stirred continuously for 6 hours. After confirming the complete consumption of raw materials by thin layer chromatography (TLC) monitoring, the reaction system was cooled to 20~25°C. The reaction was quenched by the slow addition of 50 ml of water and subsequently concentrated to dryness under reduced pressure. To the residue, 200 ml of acetone was added, cooled to 25 °C for crystallization, and the crystals were collected by filtration and dried to afford 100 g of off-white solid 3-chloro-L-alanine hydrochloride in 88.4% yield.