title: A new and recyclable system based on tropin ionic liquids for resolution of several racemic amino acids.
abstract: A new, recyclable solid-liquid resolution system was developed based on tropin ionic liquids [CnDTr][L-Pro]2for the enantiomeric resolution of racemic phenylalanine and other α-substituted carboxylic acids including tryptophan, tyrosine, benzene glycine and mandelic acid. With racemic phenylalanine as resolution model, effect factors were investigated for better resolution conditions. On the conditions, some efficient resolution were achieved, for instance the e.e. (98%) and product yield (76%) in solid phase for phenylalanine, and the e.e. 99.71% in solid phase for tryptophan. Chiral product was verified with fourier transform infrared spectroscopy (FT-IR), Raman spectrum, thermal gravity analysis (TG), elemental analysis (EA) and chiral HPLC. Further, the resolution mechanism was studied with computer molecular dynamic simulations and UV-vis. The resolution was closely related to the formation of complexes (L-Phe-Cu(Ⅱ)-L-pro-) and the spatial configuration of D/L-Phe. The system is characteristic of high resolution, no organic solvent, easy isolation of solid-liquid and recycle of all chemical materials as much as possible.
authors.affiliation: School of Chemical Engineering, Sichuan University, Chengdu 610065, China.
authors.forename: Zhixia
authors.initials: Z
authors.lastname: Wang
authors.affiliation: School of Chemical Engineering, Sichuan University, Chengdu 610065, China.
authors.forename: Zhenbo
authors.initials: Z
authors.lastname: Hou
authors.affiliation: School of Chemical Engineering, Sichuan University, Chengdu 610065, China.
authors.forename: Shun
authors.initials: S
authors.lastname: Yao
authors.affiliation: School of Chemical Engineering, Sichuan University, Chengdu 610065, China.
authors.forename: Min
authors.initials: M
authors.lastname: Lin
authors.affiliation: School of Chemical Engineering, Sichuan University, Chengdu 610065, China. Electronic address: hangsong@vip.sina.com.
authors.forename: Hang
authors.initials: H
authors.lastname: Song
mesh_terms: D000596:Amino Acids / Q000737:chemistry* / Q000302:isolation & purification*; D005591:Chemical Fractionation / Q000379:methods*; D003300:Copper / Q000737:chemistry; D006863:Hydrogen-Ion Concentration; D052578:Ionic Liquids / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D013237:Stereoisomerism; D013696:Temperature
chemical_list: D000596:Amino Acids; D052578:Ionic Liquids; D003300:Copper
keywords: Liquid-solid resolution; Racemic amino acids; Recyclable system; Resolution mechanism; Tropin ionic liquid