A new and recyclable system based on tropin ionic liquids for resolution of several racemic amino acids

A new, recyclable solid-liquid resolution system was developed based on tropin ionic liquids [CnDTr][L-Pro](2) for the enantiomeric resolution of racemic phenylalanine and other a-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(ll)-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. (C) 2017 Elsevier B.V. All rights reserved.