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The Use of N ‐Type Ligands in the Enantioselective Liquid–Liquid Extraction of Underivatized Amino Acids
Author(s) -
Verkuijl Bastiaan J. V.,
Schoonen Anne K.,
Minnaard Adriaan J.,
de Vries Johannes G.,
Feringa Ben L.
Publication year - 2010
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201000790
Subject(s) - chemistry , enantioselective synthesis , palladium , enantiomer , liquid–liquid extraction , selectivity , amino acid , extraction (chemistry) , solvent , tryptophan , organic chemistry , combinatorial chemistry , chromatography , catalysis , biochemistry
The first palladium based extraction system using chiral N ‐based ligands in the enantioselective liquid–liquid extraction (ELLE) of underivatized amino acids, is presented. The system shows the highest selectivity for the ELLE of methionine with metal complexes as hosts reported to date. Furthermore, the host can be prepared in situ from commercially available compounds. The dependency of the system on parameters such as pH, organic solvent, and temperature has been established. The intrinsic selectivity was deduced by determination of the association constants of the palladium complex with the tryptophan enantiomers.