Purification and structural characterization of 3-hydroxypropionaldehyde and its derivatives.
The compound 3-hydroxypropionaldehyde (3-HPA), together with HPA hydrate and HPA dimer, in aqueous solution forms a system with interesting chemical properties. Therefore, 3-HPA has attracted attention by the chemical industry for use as a precursor in the production of plastics, acrylic acid, and 1,3-propanediol and by the food industry, in using 3-HPA-producing Lactobacillus reuteri as a probiotic. To produce 3-HPA in high yield from glycerol, L. reuteri was used as a biotransformation system. A convenient chromatographic purification method was developed, and purified 3-HPA was analyzed using electrospray ionization mass spectrometry and (13)C NMR. Quantitative (13)C NMR revealed a concentration-dependent distribution of the three compounds forming the HPA system. At concentrations above 1.4 M, the HPA dimer was predominant. However, at concentrations relevant for biological systems, HPA hydrate was the most abundant, followed by the aldehyde form. Our results indicate that the dimeric form with expected antibiotic properties should not be the active form.
Vollenweider
Sabine
S
Laboratory of Food Biotechnology, Institute of Food Science and Nutrition, CH-8092 ETH Zentrum, Zurich, Switzerland. sabine.vollenweider@ilw.agrl.ethz.ch
Grassi
Guido
G
König
Iwo
I
Puhan
Zdenko
Z
D000447:Aldehydes; D019281:Dimerization; D019649:Food Industry; D005985:Glyceraldehyde / Q000031:analogs & derivatives* / Q000737:chemistry* / Q000302:isolation & purification* / Q000378:metabolism; D007778:Lactobacillus / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D019936:Probiotics; D011407:Propane; D012996:Solutions; D021241:Spectrometry, Mass, Electrospray Ionization; D014867:Water
D000447:Aldehydes; D012996:Solutions; D014867:Water; C047158:3-hydroxypropionaldehyde; D005985:Glyceraldehyde; D011407:Propane