Simple gas chromatographic method for the stereodifferentiation of methyl nilate, a chiral alpha-methyl-beta-hydroxy ester.
The four stereoisomers of methyl nilate, methyl 3-hydroxy-2-methylbutanoate, have been separated and analyzed by the direct simultaneous achiral-chiral high-resolution gas chromatography (HRGC) and also by the chiral high-resolution gas chromatography-time-of-flight mass spectrometry (HRGC-TOF-MS). The method involved the use of DB-5 and CP Chirasil-Dex CB columns. The elution sequences on the two columns were determined and are reported. The one-step GC method allows the identification by retention data and simultaneously to determine unequivocally the absolute configuration of nilic acid moieties contained in minor complex natural products without previous isolation, as part of a general strategy for the structure determination of the compounds.
Department of Chemistry, CQFB-Requimte, Faculty of Science and Technology, New University of Lisbon, Quinta da Torre, 2825-114 Caparica, Portugal. emg@dq.fct.unl.pt
Elvira M S M
EM
Gaspar
José G
JG
Barroso
D002087:Butyrates / Q000737:chemistry*; D002849:Chromatography, Gas / Q000379:methods*; D004952:Esters / Q000737:chemistry*; D007536:Isomerism; D013237:Stereoisomerism
D002087:Butyrates; D004952:Esters; C511087:methyl nilate