Reuterin (3-hydroxypropionaldehyde) is the organic compound with the formula HOCH2CH2CHO. It is a bifunctional molecule, containing both a hydroxy and aldehyde functional groups.
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.
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 reactionsEdit
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.
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]
ReferencesEdit
^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. PMC176032. PMID 3245697.
^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.
^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. ISBN9781845696696.
^Dietrich Arntz, Achim Fischer, Mathias Höpp, Sylvia Jacobi, Jörg Sauer, Takashi Ohara, Takahisa Sato, Noboru Shimizu and Helmut Schwind (2012). "Acrolein and Methacrolein". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a01_149.pub2.{{cite encyclopedia}}: CS1 maint: uses authors parameter (link)
^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. PMC172512. PMID 2751282.
^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.
^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.
^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.
^ abEl-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.
^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.
August 27, 2023
reuterin, hydroxypropionaldehyde, organic, compound, with, formula, hoch2ch2cho, bifunctional, molecule, containing, both, hydroxy, aldehyde, functional, groups, namespreferred, iupac, name, hydroxypropanalidentifierscas, number, 2134, model, jsmol, interactiv. 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 NamesPreferred IUPAC name 3 HydroxypropanalIdentifiersCAS Number 2134 29 43D model JSmol Interactive imageChEBI CHEBI 17871ChemSpider 67601ECHA InfoCard 100 016 696KEGG C00969PubChem CID 75049UNII I0NJE782CV YCompTox Dashboard EPA DTXSID4062199InChI InChI 1S C3H6O2 c4 2 1 3 5 h2 5H 1 3H2Key AKXKFZDCRYJKTF UHFFFAOYSA NInChI 1 C3H6O2 c4 2 1 3 5 h2 5H 1 3H2Key AKXKFZDCRYJKTF UHFFFAOYAXSMILES C CO C OPropertiesChemical formula C 3H 6O 2Molar mass 74 079 g mol 1Except 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 Contents 1 Solution structure 2 Synthesis and reactions 3 Biological activity 4 ReferencesSolution structure EditIn 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 2The 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 hydroxypropionaldehydeSynthesis and reactions Edit3 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 H2OPresently 3 hydroxypropionaldehyde is an intermediate in the production of pentaerythritol Hydrogenation of reuterin gives 1 3 propanediol Biological activity EditReuterin 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 Edit 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 Vollenweider S Grassi G Konig 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 a b c 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 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 9781845696696 Dietrich Arntz Achim Fischer Mathias Hopp Sylvia Jacobi Jorg Sauer Takashi Ohara Takahisa Sato Noboru Shimizu and Helmut Schwind 2012 Acrolein and Methacrolein Ullmann s Encyclopedia of Industrial Chemistry Weinheim Wiley VCH doi 10 1002 14356007 a01 149 pub2 a href Template Cite encyclopedia html title Template Cite encyclopedia cite encyclopedia a CS1 maint uses authors parameter link 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 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 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 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 a b 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 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 Retrieved from https en wikipedia org w index php title Reuterin amp oldid 1170978339, wikipedia, wiki, book, books, library,
