Preparative separation and identification of derivatized beta-methylphenylalanine enantiomers by chiral SFC, HPLC and NMR for development of new peptide ligand mimetics in drug discovery.
J Pharm Biomed Anal
; 40(4): 901-9, 2006 Mar 03.
Article
em En
| MEDLINE
| ID: mdl-16239092
ABSTRACT
A direct preparative purification of all four isomers of the unnatural amino acid beta-methylphenylalanine was achieved using supercritical fluid chromatography (SFC) with stacked-injection. Final purification of the Cbz-methyl ester derived isomers was performed on a Daicel Chiralpak AD-H column (20 mm x 250 mm), using 5050 methanol/ethanol as the organic modifier and resulted in purification of over 3.4 g of material in 6.25 h with >90% total recovery. The absolute stereochemical assignment of the purified amino acids was determined through a combination of chiral HPLC, NMR and optical rotation studies. To our knowledge, this is the first reported preparative approach that has yielded all four compounds in a single chromatographic run.
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Base de dados:
MEDLINE
Assunto principal:
Desenho de Fármacos
/
Cromatografia com Fluido Supercrítico
/
Aminobutiratos
Tipo de estudo:
Diagnostic_studies
Idioma:
En
Ano de publicação:
2006
Tipo de documento:
Article