Synthesis of CuPF 6 -(S)-BINAP loaded resin and its enantioselectivity toward phenylalanine enantiomers

• Published in: Chirality (New York, N.Y.) N.Y.), 2017-09, Vol.29 (9), p.541-549
• Main Authors: Liu, Xiong, Zhou, Wenqi, Xu, Longqi
• Format: Article
• Language: English
• Subjects: Adsorption; Chemistry Techniques, Synthetic; Copper - chemistry; Hydrogen-Ion Concentration; Naphthalenes - chemistry; Organometallic Compounds - chemical synthesis; Organometallic Compounds - chemistry; Phenylalanine - chemistry; Phenylalanine - isolation & purification; Resins, Synthetic - chemistry; Stereoisomerism; Temperature
• ISSN: 0899-0042; 1520-636X
• DOI: 10.1002/chir.22725

A type of resin-anchored CuPF -(S)-BINAP was synthesized and identified. The PS-CuPF -(S)-BINAP resin was used to adsorb the phenylalanine enantiomers. The results showed that the adsorption capacity of PS-CuPF -(S)-BINAP resin toward L-phenylalanine was higher than that of resin toward D-phenylalanine. PS-CuPF -(S)-BINAP resin exhibited good enantioselectivity toward L-phenylalanine and D-phenylalanine. The influence of phenylalanine concentration, pH, adsorption time, and temperature on the enantioselectivity of the resin were investigated. The results showed that the enantioselectivity of the resin increased with increasing the phenylalanine concentration, pH, and adsorption time, while it decreased with an increase in temperature. The causes for these influences are discussed. The highest enantioselectivity (α = 2.81) was obtained when the condition of phenylalanine concentration was 0.05 mmol/mL, pH was 8, adsorption time was 12 h, and temperature 5°C. The desorption test for removing D/L-phenylalanine on PS-CuPF -(S)-BINAP resin was also investigated. The desorption ratios of D-phenylalanine and L-phenylalanine at pH of 1 were 95.7% and 94.3%, respectively. This result indicated that the PS-CuPF -(S)-BINAP resin could be regenerated by shaking with an acidic solution. The reusability of the PS-CuPF -(S)-BINAP resin was also assessed and the resin exhibited considerable reusability.