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HPLC enantioselective separation of aromatic amino and hydrazino acids on a teicoplanin stationary phase and the enantiomeric purity determination of L ‐isomers used as drugs
Author(s) -
Doležalová Milada,
Tkaczyková Magda
Publication year - 1999
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/(sici)1520-636x(1999)11:5/6<394::aid-chir8>3.0.co;2-r
Subject(s) - chemistry , enantiomer , chromatography , high performance liquid chromatography , enantioselective synthesis , triethylamine , chirality (physics) , acetic acid , phase (matter) , polyethylene glycol , organic chemistry , catalysis , chiral symmetry breaking , physics , quantum mechanics , nambu–jona lasinio model , quark
A glycopeptide antibiotic (teicoplanin) bonded stationary phase was employed for liquid chromatographic enantioseparation of dopa, α‐methyldopa, carbidopa, and several other structurally related compounds. The influence of mobile phase composition in both reversed‐phase and polar organic modes was investigated. Using a hydroorganic mobile phase, complete enantioseparations of α‐methylamino acids were not attained. However, this type of separation is suitable for the enantiomers of dopa. In polar organic mode, a simple mobile phase composed of methanol and the polar additives triethylamine and acetic acid at very low concentrations was suggested. With the exceptions of α‐methyltyrosine and α‐methylphenylalanine, baseline enantioseparations of all investigated compounds were achieved. Liquid chromatographic methods based on the described enantioseparations proved to be useful for the enantiomeric purity determination of the single enantiomeric drugs levodopa, methyldopa, and carbidopa. Chirality 11:394–403, 1999. © 1999 Wiley‐Liss, Inc.