Reuterin

Reuterin (3-hydroxypropionaldehyde) is the organic compound with the formula HOCH2CH2CHO. It is a bifunctional molecule, containing both a hydroxy and aldehyde functional groups.

Reuterin
Names
Preferred IUPAC name
3-Hydroxypropanal
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.016.696
KEGG
UNII
  • 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
  • C(CO)C=O
Properties
C3H6O2
Molar mass 74.079 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

The name reuterin is derived from Lactobacillus reuteri, which produces the compound biosynthetically from glycerol as a broad-spectrum antibiotic (bacteriocin).[1] L. reuteri itself is named after the microbiologist Gerhard Reuter, who did early work in distinguishing it as a district species.

Solution structure

In aqueous solution 3-hydroxypropionaldehyde exists in equilibrium with its hydrate (1,1,3-propanetriol), in which the aldehyde group converts to a geminal diol:

HOCH2CH2CHO + H2O → HOCH2CH2CH(OH)2

The hydrate is also in equilibrium with its dimer (2-(2-hydroxyethyl)-4-hydroxy-1,3-dioxane), which dominates at high concentrations. These three components - the aldehyde, its dimer, and the hydrate are therefore in a dynamic equilibrium.[2]

Besides, 3-hydroxypropionaldehyde suffers an spontaneous dehydration in aqueous solution, and the resulting molecule is called acrolein.[3]

In fact, the term reuterin is the name given to the dynamic system formed by 3-hydroxypropionaldehyde, its hydrate, the dimer, and acrolein. This last molecule, acrolein, was recently included in reuterin definition.[3][4]

Structure of the dimer of 3-hydroxypropionaldehyde

Synthesis and reactions

3-Hydroxypropionaldehyde is formed by the condensation of acetaldehyde and formaldehyde. This reaction, when conducted in the gas-phase, was the basis for a now obsolete industrial route acrolein:[5]

CH3CHO + CH2O → HOCH2CH2CHO
HOCH2CH2CHO → CH2=CHCHO + H2O

Presently 3-hydroxypropionaldehyde is an intermediate in the production of pentaerythritol. Hydrogenation of reuterin gives 1,3-propanediol.

Biological activity

Reuterin is an intermediate in the metabolism of glycerol to 1,3-propanediol catalysed by the coenzyme B12-dependent glycerol dehydratase.

Reuterin is a potent antimicrobial compound produced by Lactobacillus reuteri. It is an intermediate in the metabolism of glycerol to 1,3-propanediol catalysed by the coenzyme B12-dependent diol dehydrase. It inhibits the growth of some harmful Gram-negative and Gram-positive bacteria, along with yeasts, molds, and protozoa.[6] 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.[7]

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.[8][9][10]

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.[3][10] It has also been demonstrated to kill Escherichia coli O157:H7 when produced by L. reuteri.[11]

References
  1. Talarico TL, Casas IA, Chung TC, Dobrogosz WJ (December 1988). "Production and isolation of reuterin, a growth inhibitor produced by Lactobacillus reuteri". Antimicrobial Agents and Chemotherapy. 32 (12): 1854–8. doi:10.1128/AAC.32.12.1854. PMC 176032. PMID 3245697.
  2. Vollenweider S, Grassi G, König I, Puhan Z (May 2003). "Purification and structural characterization of 3-hydroxypropionaldehyde and its derivatives". Journal of Agricultural and Food Chemistry. 51 (11): 3287–93. doi:10.1021/jf021086d. PMID 12744656.
  3. Engels C, Schwab C, Zhang J, Stevens MJ, Bieri C, Ebert MO, McNeill K, Sturla SJ, Lacroix C (November 2016). "Acrolein contributes strongly to antimicrobial and heterocyclic amine transformation activities of reuterin". Scientific Reports. 6 (1): 36246. Bibcode:2016NatSR...636246E. doi:10.1038/srep36246. PMC 5098142. PMID 27819285.
  4. Stevens M, Vollenweider S, Lacroix C (2011). "The potential of reuterin produced by Lactobacillus reuteri as a broad spectrum preservative in food". Protective Cultures, Antimicrobial Metabolites and Bacteriophages for Food and Beverage Biopreservation. Elsevier. pp. 129–160. doi:10.1533/9780857090522.1.129. ISBN 978-1-84569-669-6.
  5. Dietrich Arntz; Achim Fischer; Mathias Höpp; Sylvia Jacobi; Jörg Sauer; Takashi Ohara; Takahisa Sato; Noboru Shimizu; Helmut Schwind (2012). "Acrolein and Methacrolein". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a01_149.pub2.
  6. Talarico TL, Dobrogosz WJ (May 1989). "Chemical characterization of an antimicrobial substance produced by Lactobacillus reuteri". Antimicrobial Agents and Chemotherapy. 33 (5): 674–9. doi:10.1128/aac.33.5.674. PMC 172512. PMID 2751282.
  7. Casas IA, Dobrogosz WJ (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): 247–285. doi:10.1080/08910600050216246-1.
  8. Vollenweider S, Lacroix C (March 2004). "3-hydroxypropionaldehyde: applications and perspectives of biotechnological production" (PDF). Applied Microbiology and Biotechnology. 64 (1): 16–27. doi:10.1007/s00253-003-1497-y. hdl:20.500.11850/51119. PMID 14669058. S2CID 27112296.
  9. Axelsson LT, Chung TC, Dobrogosz WJ, Lindgren SE (1989). "Production of a Broad Spectrum Antimicrobial Substance by Lactobacillus reuteri". Microbial Ecology in Health and Disease. 2 (2): 131–136. doi:10.3109/08910608909140210.
  10. 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. doi:10.4315/0362-028X-62.3.257. PMID 10090245.
  11. 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. doi:10.4315/0362-028X-66.11.2038. PMID 14627280.
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