Purification and structural characterization of 3-hydroxypropionaldehyde and its derivatives

Journal of Agricultural and Food Chemistry

Volumn 51, Issue 11, 2003, Pages 3287-3293

  Vollenweider, Sabine ^a   Grassi, Guido ^a   König, Iwo ^a   Puhan, Zdenko ^a  

^a ETH ZURICH   (Switzerland)

Author keywords

3 hydroxypropionaldehyde; 13C NMR; Biotransformation; ESI MS; Probiotic; Reuterin

Indexed keywords

3 HYDROXPROPIONALDEHYDE; PROBIOTIC AGENT; PROPIONALDEHYDE; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; ARTICLE; BIOTRANSFORMATION; CARBON NUCLEAR MAGNETIC RESONANCE; DEHYDRATION; DERIVATIZATION; FOOD INDUSTRY; MASS SPECTROMETRY; PROTEIN PURIFICATION; QUANTITATIVE ANALYSIS; STRUCTURE ANALYSIS;

ALDEHYDES; DIMERIZATION; FOOD INDUSTRY; GLYCERALDEHYDE; LACTOBACILLUS; MAGNETIC RESONANCE SPECTROSCOPY; PROBIOTICS; PROPANE; SOLUTIONS; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; WATER;

LACTOBACILLUS; LACTOBACILLUS REUTERI;

EID: 0037609671     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf021086d     Document Type: Article

References (42)

1. Voisenet, M. E. Formation d'acroléine dans la maladie de l'amertume des vins. C. R. Acad. Sci. 1910, t. 150, 1614-1616.
2. Slininger, P. J.; Bothast, R. J. Optimizing aerobic conversion of glycerol to 3-hydroxypropionaldehyde. Appl. Environ. Microbiol. 1985, 50, 1444-1450.
3. Barbirato, F.; Grivet, J. P.; Soucaille, P.; Bories, A. 3-Hydroxy-propionaldehyde, an inhibitory metabolite of glycerol fermentation to 1,3-propanediol by enterobacterial species. Appl. Environ. Microbiol. 1996, 62, 1448-1451.
4. Mills, E.; Baugh, W. D.; Conner, H. A. Studies on the formation of acrolein in distillery mashes. Appl. Microbiol. 1954, 2, 9-13.
5. Serjak, W. C.; Day, W. H.; Van Lanen, J. M.; Boruff, C. S. Acrolein production by bacteria found in distillery grain mashes. Appl. Microbiol. 1954, 2, 14-20.
6. http://brenda.bc.uni-koeln.de/php/result_flat.php3?ecno=4.2.1.30, 2002.
7. Voisenet, M. E. Sur un ferment, contenu dans les eaux, agent de déshydratation de la glycérine. C. R. Acad. Sci. 1914, 158, 195-197.
8. Abeles, R. H.; Brownstein, A. M.; Randles, C. H. β-Hydroxy-propionaldehyde, an intermediate in the formation of 1,3-propanediol by Aerobacter aerogenes. Biochim. Biophys. Acta 1960, 41, 530-531.
9. Smiley, K. L.; Sobolov, M. A cobamide-requiring glycerol dehydrase from an acrolein-forming Lactobacillus. Arch. Biochem. Biophys. 1962, 97, 538-543.
10. + oxidoreductase. J. Bacteriol. 1987, 169, 2050-2054.
11. Schütz, H.; Radler, F. Anaerobic reduction of glycerol to propanediol-1.3 by Lactobacillus brevis and Lactobacillus buchneri. Syst. Appl. Microbiol. 1984, 5, 169-178.
12. Abbad-Andaloussi, S.; Amine, J.; Gerard, P.; Petitdemange, H. Effect of glucose on glycerol metabolism by Clostridium butyricum DSM 5431. J. Appl. Microbiol. 1998, 84, 515-522.
13. Sobolov, M.; Smiley, K. L. Metabolism of glycerol by an acrolein-forming Lactobacillus. J. Bacteriol. 1960, 79, 261- 266.
14. Sauvageot, N.; Gouffi, K.; Laplace, J. M.; Auffray, Y, Glycerol metabolism in Lactobacillus collinoides: production of 3-hydroxypropionaldehyde, a precursor of acrolein. Int. J. Food Microbiol. 2000, 55, 167-170.
15. El-Ziney, M. G.; Arneborg, N.; Uyttendaele, M.; Debevere, J.; Jakobsen, M. Characterization of growth and metabolite production of Lactobacillus reuteri during glucose/glycerol cofermentation in batch and continuous cultures. Biotechnol. Lett. 1998, 20, 913-916.
16. Hall, R. H.; Stern, E. S. Acid-catalysed hydration of acrylaldehyde: Kinetics of the reaction and isolation of β-hydroxypropionaldehyde. J. Chem. Soc. 1950, 490-498.
17. 1H NMR study of formaldehyde reactions with acetaldehyde and acrolein. Synthesis of 2-(hydroxymethyl)-1,3-propanediol. Pol. J. Chem. 1981, 55, 1393-1403.
18. Axelsson, L.; Chung, T. C.; Dobrogosz, W. J.; Lindgren, S. E. Production of a broad-spectrum antimicrobial substance produced by Lactobacillus reuteri. Microb. Ecol. Health Dis. 1988, 2, 131-136.
19. Kandler, O.; Stetter, K.-O.; Lagnado, J. R. Lactobacillus reuteri sp. nov., a new species of heterofermentative Lactobacilli. Zbl. Bakt. Hyg., 1. Abt. Orig. C 1980, 1, 264-269.
20. Talarico, T. L.; Dobrogosz, W. J. Chemical characterization of an antimicrobial substance produced by Lactobacillus reuteri. Antimicrob. Agents Chemother. 1989, 33, 674-679.
21. Dobrogosz, W. J.; Lindgren, S. E. Antibiotic reuterin. PCT/US88/01423, 1988.
22. Tannock G. W. Probiotics: A Critical Review; Horizon Scientific Press: Wymondham, Norfolk, U.K., 1999.
23. Daeschel, M. A. Antimicrobial substances from lactic acid bacteria for use as food preservatives. Food Technol. 1989, 43, 164-167.
24. El-Ziney, M. G.; Debevere, J. The effect of reuterin on Listeria monocytogenes and Escherichia coli O157:H7 in milk and Cottage cheese. J. Food Prot. 1998, 61, 1275-1280.
25. El-Ziney, M. G.; van-den-Tempel, T.; Debevere, J.; Jakobsen, M. Application of reuterin produced by Lactobacillus reuteri 12002 for meat decontamination and preservation. J. Food Prot. 1999, 62, 257-261.
26. Kandler, O. Validation of the publication of new names and new combinations previously effectively published outside the IJSB. List No. 8. Int. J. Syst. Bacteriol. 1982, 32, 266-268.
27. Rahn, C. H.; Schlenk, H. Detection of aldehydes with 4-amino5-hydrazino-1,2,4-triazole-3-thiol as spray reagent. Lipids 1973, 8, 612-616.
28. Circle, S. J.; Stone, L.; Boruff, C. S. Acrolein determination by means of tryptophane. Ind. Eng. Chem. 1945, 17, 259-262.
29. 2SO solutions. Magn. Reson. Chem. 1988, 26, 523-525.
30. Braun, S.; Kalinowski, H.-O.; Berger, S. 100 and More Basic NMR Experiments; Verlag Chemie: Weinheim, 1996.
31. Chung, T. C.; Axelsson, L.; Lindgren, S. E.; Dobrogosz, W. J. In vitro studies on reuterin synthesis by Lactobacillus reuteri. Microb. Ecol. Health Dis. 1989, 2, 137-144.
32. Luthi-Peng, Q.; Scharer, S.; Puhan, Z. Production and stability of 3-hydroxypropionaldehyde in Lactobacillus reuteri. Appl. Microbiol. Biotechnol. 2002, 60, 73-80.
33. Nakano, T.; Takanobu, T.; Yasutaka, I.; Masaya, O. Chemoselective oxidation of the primary alcohol function of diols catalyzed by zirconocene complexes. Synthesis 1986, 9, 774-776.
34. Talarico, T. L.; Casas, I. A.; Chung, T. C.; Dobrogosz, W. J. Production and isolation of reuterin, a growth inhibitor produced by Lactobacillus reuteri. Antimicrob. Agents Chemother. 1988, 32, 1854-1858.
35. Vancauwenberge, J. E.; Slininger, P. J.; Bothast, R. J. Bacterial conversion of glycerol to β-hydroxypropionaldehyde. Appl. Environ, Microbiol. 1990, 56, 329-332.
36. Claisse, O.; Lonvaud-Funel, A. Primers and a specific DNA probe for detecting lactic acid bacteria producing 3-hydroxypropionaldehyde from glycerol in spoiled ciders. J. Food Prot. 2001, 64, 833-837.
37. Yunmbam, M. K.; Roberts, J. F. The in vitro efficacy of reuterin on the culture and bloodstream forms of Trypanosoma brucei brucei. Comp. Biochem. Physiol., C: Pharmacol., Toxicol. Endocrinol. 1992, 101, 235-238.
38. Le Hénaff, P. Sur les équilibres et les vitesse d'hydratation et d'hemiacétalisation des aldéhydes aliphatiques. C. R. Acad. Sci. 1967, t. 265, 175-178.
39. Schauenstein, E.; Esterbauer, H.; Zollner, H. Saturated aldehydes. Aldehydes in Biological Systems: Their Natural Occurrence and Biological Activities; Pion: London, 1977.
40. Esterbauer, H.; Schaur, R. J.; Zollner, H. Chemistry and biochemistry of 4-hydroxynonenal, malonaldehyde and related aldehydes. Free Radical Biol. Med. 1991, 11, 81-128.
41. Yunmbam, M. K.; Roberts, J. F. In vivo evaluation of reuterin and its combinations with suramin, melarsoprol, DL-alpha-difluoromethylornithine and bleomycin in mice infected with Trypanosoma brucei brucei. Comp. Biochem. Physiol., C: Pharmacol., Toxicol. Endocrinol. 1993, 105, 521-524.
42. Chen, C. N.; Sung, H. W.; Liang, H. F.; Chang, W. H. Feasibility study using a natural compound (reuterin) produced by Lacto-bacillus reuteri in sterilizing and cross-linking biological tissues. J. Biomed. Mater. Res. 2002, 61, 360-369.