Formation of a pyridinium derivative by reaction of 4-hydroxypentenal with glycine.
4-Hydroxypentenal reacts with glycine in a slightly alkaline (pH 8.8) aqueous solution to 1-(1-carboxymethyl)-3-(2-hydroxypropyl)-pyridinium betaine. The yield of the pyridinium betaine isolated by preparative HPLC was 20 mol% and its structure was ascertained by 13C-NMR, IR, UV and mass spectroscopy. Several other products could be detected by HPLC in the 4-hydroxpentenal-glycine reaction mixture, their instability, however, impeded their preparative isolation. 4-Hydroxyalkenals are toxic products generated during lipid peroxidation and the results described explain in part the mechanism how these aldehydes react with nucleophilic amino groups in tissue.
Napetschnig
S
S
Institute of Biochemistry, University of Graz, Austria.
Schauenstein
E
E
Esterbauer
H
H
D000447:Aldehydes; D055598:Chemical Phenomena; D002621:Chemistry; D002851:Chromatography, High Pressure Liquid; D005998:Glycine; D006863:Hydrogen-Ion Concentration; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D015394:Molecular Structure; D011726:Pyridinium Compounds; D012996:Solutions; D013053:Spectrophotometry
D000447:Aldehydes; D011726:Pyridinium Compounds; D012996:Solutions; C058440:1-(1-carboxymethyl)-3-(2-hydroxypropyl)pyridinium betaine; D005998:Glycine