Chiral ligand-exchange separation and resolution of extremely rigid glutamate analogs: 1-aminospiro[2.2]pentyl-1,4-dicarboxylic acids.
Anal Bioanal Chem
; 397(5): 1997-2011, 2010 Jul.
Article
em En
| MEDLINE
| ID: mdl-20496034
ABSTRACT
Owing to their chelation ability, a series of fully constrained L-Glu analogs formed by the spiro-union of two cyclopropane rings (1-aminospiro[2.2]pentyl-1,4-dicarboxylic acids, ASPED A-D), was submitted to chiral ligand-exchange chromatographic (CLEC) analysis. As the initial step, two methodologically different chiral devices were evaluated. A chiral stationary phase (CSP) obtained by dynamic coating of C(18) chains with the S-trityl-(R)-cysteine ((R)-STC) was used first with this objective. The lack of separation of the enantiomers of ASPED C and D prompted us to utilize the chiral mobile phase (CMP) prepared from O-benzyl-(S)-serine ((S)-OBS). The latter afforded complete separation of the four pairs of enantiomers. For all the pairs, quantum mechanical investigations shed light on the main features responsible for the different enantiomer recognition mechanism with (S)-OBS. The validated analytical method was then fruitfully adopted for semi-preparative-scale isolation of the enantiomers of ASPED C.
Texto completo:
1
Base de dados:
MEDLINE
Assunto principal:
Cromatografia por Troca Iônica
/
Ácido Glutâmico
Tipo de estudo:
Evaluation_studies
Idioma:
En
Revista:
Anal Bioanal Chem
Ano de publicação:
2010
Tipo de documento:
Article
País de afiliação:
Itália