title: Facile determination of the absolute configurations of α-hydroxy acids by chiral derivatization coupled with liquid chromatography-mass spectrometry analysis.
abstract: α-Hydroxy acids are commonly encountered in natural bioactive molecules. For convenient determination of the absolute configurations of α-hydroxy acids, a simple method, named the "O-Marfey method" was developed using a chiral derivatization strategy with (L-fluoro-2,4-dinitrophenyl-5)-L-alanine amide (L-FDAA). The liquid chromatography-mass spectrometry (LC-MS) analysis of the derivatives clearly determined the absolute configurations of various α-hydroxy acids based on their elution times and sequences. This new method is operationally simple with short reaction time and sensitive enough for application at a sub-milligram scale without any purification. This method also enables the simultaneous chirality analysis of α-hydroxy acids and α-amino acids. The absolute configuration of a natural depsipeptide bearing an α-hydroxy acid and α-amino acids was successfully determined by our O-Marfey application.
authors.affiliation: Natural Products Research Institute, College of Pharmacy, Seoul National University, 1 Gwanak-ro, Gwanak-gu, Seoul 151-742, Republic of Korea.
authors.forename: Kyuho
authors.initials: K
authors.lastname: Moon
authors.forename: Chaemin
authors.initials: C
authors.lastname: Lim
authors.forename: Sanghee
authors.initials: S
authors.lastname: Kim
authors.forename: Dong-Chan
authors.initials: DC
authors.lastname: Oh
mesh_terms: D001688:Biological Products / Q000032:analysis; D002853:Chromatography, Liquid; D006880:Hydroxy Acids / Q000032:analysis* / Q000737:chemistry*; D007930:Leucine / Q000031:analogs & derivatives / Q000737:chemistry; D013058:Mass Spectrometry / Q000379:methods*; D008958:Models, Molecular; D008968:Molecular Conformation; D009574:Nitro Compounds / Q000737:chemistry; D013816:Thermodynamics
chemical_list: C439871:1-fluoro-2,4-dinitrophenyl-5-leucinamide; D001688:Biological Products; D006880:Hydroxy Acids; D009574:Nitro Compounds; D007930:Leucine