Use of esters of N-hydroxysuccinimide in the synthesis of N-acylamino acids

The structure and phase diagram of chiral alkyl-serine monolayers on mercury

“…The molecules were synthesized following ref. 28. The sequence of reactions for producing the C n -serine molecules is shown in Fig.…”

Enantioselective crystallization in miniemulsions based on chiral surfactants

“…N-stearoyl D-or L-serine form micelles in water with a unique chiral surface, 23 which may provide an effective template for selective chiral crystallization. The chiral surfactants, D-and L-stearoyl serine, were prepared by coupling a stearic acid N-hydroxy succinimide ester with L-or D-serine, as described by Lapidot et al 24 All miniemulsions were prepared on a (W/O) basis by mixing appropriate percentages of n-octanol, a chiral surfactant and water (HPLC-grade) in a 20 mL vessel. The mixtures were sonicated for 2 min by a highintensity ultrasonic probe (Sonics VCX-750 1 cm 2 titanium horn, 20 kHz, 40 W).…”

Mirror Symmetry Breaking in Micelles of N-Stearoyl Serine Enantiomers

“…Stearic acid, N-hydroxysuccinimide, ethyl acetate, dicyclohexylcarbodiimide, ethanol, tetrahydrofuran, L and D serine, sodium bicarbonate, hydrochloric acid and acetone were purchased from Sigma Aldrich. The chiral surfactants, D-and L-stearoyl serine, (D-NSS and L-NSS) were prepared by coupling stearic acid N-hydroxy succinimide ester with D and L serine, as described by Lapidot et al (11) . The structures and compositions of the D-NSS and L-NSS were confirmed by 1 H-NMR, mass spectroscopy, infrared spectra and optical rotation.…”