Uses
N-Cbz-D-valine is the N-Cbz-protected form of D-Valine (V094200). D-Valine (an isomer of the essential amino acid L-Valine [V094205])exhibited inhibitory effects on fibroblasts that contaminated mammalian kidney cultures, allowing for selective growth epithelial cells. D-Valine is also known for its presence in the structure of Actinomycin D, an antitumour drug. D-Valine is naturally synthesized by Streptomyces antibioticus.
Synthesis
At 0C, 10 mmol of D-valine was dissolved in 50 ml of a saturated solution of sodium bicarbonate (NaHCO3) at this temperature to obtain the dissolved solution, and the reaction was carried out with 11 mmol of benzyl chloroformate added dropwise to the dissolved solution at a rate of 1 drop/10 s while stirring, dropwise
Finished, placed at 30 , stirring reaction 15 hours, do thin layer detection, measured that the solution is completely reacted, and then washed with 50 ml / times of ether 3 times, discard the ether, get the aqueous phase, the aqueous phase with a mass concentration of 30% of the concentrated hydrochloric acid adjusted PH to 3, the emergence of milky white solids, on the emergence of milky white solids after the liquid was extracted with 50 ml / time of ethyl acetate for 3 times, merged, and combined the liquid in turn, the combined solution was extracted with 50 ml / time of ethyl acetate, the combined liquid with 50 ml / time of ethyl acetate, the combined liquid with 50 ml The combined solution was sequentially extracted with 50 ml/time of ethyl acetate.
The combined solution was washed twice with 50 ml/time of distilled water and once with 50 ml of saturated saline, then dried with anhydrous magnesium sulfate for 7 hours, filtered, and the filtrate was concentrated under reduced pressure to obtain a light yellow oil, which was purified by chromatography column using mixed solvent of ethyl acetate and petroleum ether with the ratio of 1:3 by volume as the mobile phase, and was obtained as N-Cbz-D-valine, which was a colorless, light-white solid. -Valine, as colorless transparent oil, the yield was 68.7%.
