Reuterin

Reuterin

Names
IUPAC name 3-Hydroxypropanal
Identifiers
ChemSpider	67601
Jmol interactive 3D	Image
PubChem	75049
InChI InChI=1S/C3H6O2/c4-2-1-3-5/h2,5H,1,3H2 Key: AKXKFZDCRYJKTF-UHFFFAOYSA-N InChI=1/C3H6O2/c4-2-1-3-5/h2,5H,1,3H2 Key: AKXKFZDCRYJKTF-UHFFFAOYAX
SMILES C(CO)C=O
Properties
Chemical formula	C3H6O2
Molar mass	74.079
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Reuterin is a potent antimicrobial multi-compound produced by Lactobacillus reuteri, during the metabolism of glycerol to 1,3-propanediol catalysed by the coenzyme B12-dependent diol dehydrase. Reuterin consists of 3-hydroxypropionaldehyde, its hydrate, and its dimer in dynamic equilibrium.^[1][2] At concentrations above 1.4M, the HPA dimer is predominant; at concentrations relevant for biological systems, however, HPA hydrate is the most abundant, followed by the aldehyde form.^[3]

Reuterin inhibits the growth of some harmful Gram-negative and Gram-positive bacteria, along with yeasts, molds, and protozoa.^[4] L. reuteri can secrete sufficient amounts of reuterin to inhibit the growth of harmful gut organisms, without killing beneficial gut bacteria, allowing L. reuteri to remove gut invaders while keeping normal gut flora intact.^[5]

Reuterin is water-soluble, effective in a wide range of pH, resistant to proteolytic and lipolytic enzymes, and has been studied as a food preservative or auxiliary therapeutic agent.^[6][7][8]

Efficacy

Reuterin as an extracted compound has been shown capable of killing Escherichia coli O157:H7 and Listeria monocytogenes, with the addition of lactic acid increasing its efficacy.^[9] It has also been demonstrated to kill Escherichia coli O157:H7 when produced by L. reuteri.^[10]

References

1. Hall RH, Stern ES (1950). "Acid-catalysed hydration of acrylalde. Kinetics of the reaction and isolation of β-hydroxypropionaldehyde". J Chem Soc: 490–8. doi:10.1039/jr9500000490.
2. Nielsen AT, Moore DW, Schuetze Jr. A. "¹³C and ¹H NMR study of formaldehyde reactions with acetaldehyde and acrolein. Synthesis of 2-(hydroxymethyl)-1,3-propanediol". Pol J Chem 55: 1393–1403.
3. Vollenweider S, Grassi G, König I, Puhan Z (May 2003). "Purification and structural characterization of 3-hydroxypropionaldehyde and its derivatives". J. Agric. Food Chem. 51 (11): 3287–93. doi:10.1021/jf021086d. PMID 12744656.
4. Talarico TL, Dobrogosz WJ (May 1989). "Chemical characterization of an antimicrobial substance produced by Lactobacillus reuteri". Antimicrob. Agents Chemother. 33 (5): 674–9. doi:10.1128/aac.33.5.674. PMC 172512. PMID 2751282.
5. Casas, Ivan A., Dobrogosz, Walter J. (December 1, 2000). "Validation of the Probiotic Concept: Lactobacillus reuteri Confers Broad-spectrum Protection against Disease in Humans and Animals". Microbial Ecology in Health and Disease 12 (4).
6. Vollenweider S, Lacroix C: 3-hydroxypropionaldehyde: applications and perspectives of biotechnological production. Appl Microbiol Biotechnol 2004, 64(1):16-27.
7. Axelsson LT, Chung TC, Dobrogosz WJ, Lindgren SE: Production of a broad spectrum antimicrobial substance by Lactobacillus reuteri. Microb Ecol Health Dis 1989, 2:131-136.
8. El-Ziney MG, 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(3):257-261.
9. El-Ziney, MG; van den Tempel, T; Debevere, J; Jakobsen, M (March 1999). "Application of reuterin produced by Lactobacillus reuteri 12002 for meat decontamination and preservation.". Journal of food protection 62 (3): 257–61. PMID 10090245. Cite uses deprecated parameter |coauthors= (help)
10. Muthukumarasamy, P; Han, JH; Holley, RA (November 2003). "Bactericidal effects of Lactobacillus reuteri and allyl isothiocyanate on Escherichia coli O157:H7 in refrigerated ground beef.". Journal of food protection 66 (11): 2038–44. PMID 14627280.