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Chiral Ligand‐Exchange Resolution of Underivatized Amino Acids on a Dynamically Modified Stationary Phase for RP‐HPTLC
Author(s) -
Remelli Maurizio,
Faccini Stefania,
Conato Chiara
Publication year - 2014
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.22324
Subject(s) - chemistry , pyridine , ligand (biochemistry) , chiral derivatizing agent , chromatography , chiral column chromatography , high performance liquid chromatography , phase (matter) , alkylation , amino acid , asymmetric carbon , organic chemistry , combinatorial chemistry , optically active , catalysis , biochemistry , receptor
The synthesis of Spi(τ‐dec), derived from the selective alkylation of L‐spinacine (4,5,6,7‐tetrahydro‐1 H ‐imidazo[4,5‐c]pyridine‐6‐carboxylic acid) at the τ‐nitrogen of its heteroaromatic ring, with a linear hydrocarbon chain of 10 carbon atoms, is described here for the first time. Spi(τ‐dec) was successfully employed in the past to prepare home‐made chiral columns for chiral ligand‐exchange high‐performance liquid chromatography . In the present article a new method is described, using Spi(τ‐dec) as a chiral selector in high‐performance thin‐layer chromatography (HPTLC): commercial hydrophobic plates were first coated with Spi(τ‐dec) and then treated with copper sulfate. The performance of this new chiral stationary phase was tested against racemic mixtures of aromatic amino acids , after appropriate optimization of both the conditions of preparation of the plates and the mobile phase composition. The enantioselectivity values obtained for the studied compounds were higher than those reported in the literature for similar systems. The method employed here for the preparation of chiral HPTLC plates proved practical, efficient, and inexpensive. Chirality 26:313–318, 2014 . © 2014 Wiley Periodicals, Inc.