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Investigation of Taniaphos as a chiral selector in chiral extraction of amino acid enantiomers
Author(s) -
Xiao Wenjie,
Chen Shuhuan,
Liu Xiong,
Ma Yu
Publication year - 2021
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.23309
Subject(s) - chemistry , enantiomer , extraction (chemistry) , stereoselectivity , amino acid , steric effects , chiral derivatizing agent , chiral column chromatography , enantiomeric excess , phenylalanine , chiral ligand , stereochemistry , chromatography , combinatorial chemistry , enantioselective synthesis , organic chemistry , catalysis , biochemistry
Finding chiral selector with high stereoselectivity to a variety of amino acid enantiomers remains a challenge and warrants further research. In this work, Taniaphos, a chiral ligand with rotatable spatial configuration, was employed as a chiral extractant to enantioseparate various amino acid enantiomers. Phenylalanine (Phe), homophenylalanine (Hphe), 4‐nitrophenylalanine (Nphe), and 3‐chloro‐phenylglycine (Cpheg) were used as substrates to evaluate the extraction efficiency. The results revealed that Taniaphos‐Cu exhibited good abilities to enantioseparate Phe, Hphe, Nphe, and Cpheg with the highest separation factors ( α ) of 3.13, 2.10, 2.32, and 2.14, respectively. Taniaphos‐Cu is more conducive to combine with D‐amino acid in extraction. The influences of pH, Taniaphos‐Cu, and concentration and extraction temperature on extraction were comprehensively evaluated. The highest performance factors ( pf ) for Phe, Hphe, Nphe, and Cpheg at optimal extraction conditions were 0.08892, 0.1250, 0.09621, and 0.08021, respectively. The recognition mechanism between Taniaphos‐Cu and amino acid enantiomers was discussed. The coordination interaction between Taniaphos‐Cu and COO − , π‐π interaction between Taniaphos‐Cu and amino acid enantiomers are important acting forces in chiral extraction. The steric‐hindrance between NH 2 and OH lead to Taniaphos‐Cu‐D‐Phe is more stable than Taniaphos‐Cu‐L‐Phe. This work provided a chiral extractant that has good abilities to enantioseparate various amino acid enantiomers.