Characterisation of the 1H and 13C NMR spectra of methylcitric acid.
Methylcitric acid (MCA) was synthesised in Reformatsky reaction (2RS, 3RS stereoisomers) and in the nucleophilic addition (2RS, 3SR stereoisomers). The stereoselectivity of these reactions was analysed. (1)H and (13)C NMR spectra of diastereoisomers of methylcitric acid were recorded and interpreted. The values of (1)H chemical shifts and (1)H-(1)H coupling constants were analysed. Proton-decoupled high-resolution (13)C NMR spectra of MCA diastereoisomers were measured in a series of dilute water solutions of various acidities. These data may provide a basis for unequivocal determination of the presence of MCA in the urine samples of patients' suffering from propionic acidemia, methylmalonic aciduria, or holocarboxylase synthetase deficiency. NMR spectroscopy enables determination of MCA diastereoisomers in body fluids and can be a complementary and useful diagnostic tool.
Krawczyk
Hanna
H
Warsaw University of Technology, Faculty of Chemistry, Noakowskiego 3, 00-664 Warsaw, Poland. hkraw@ch.pw.edu.pl
Martyniuk
Tomasz
T
D001826:Body Fluids / Q000737:chemistry; D002247:Carbon Isotopes / Q000032:analysis; D002951:Citrates / Q000032:analysis / Q000138:chemical synthesis / Q000737:chemistry*; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D011522:Protons; D013237:Stereoisomerism
D002247:Carbon Isotopes; D002951:Citrates; D011522:Protons; C031605:2-methylcitric acid