The Biocatalytic Production of 3-Hydroxypropionaldehyde and Evaluation of Its Stability

Ju, Jung-Hyun; Jeon, Sang-Gyu; Lee, Kyung Min; Heo, Sun-Yeon; Kim, Min‐Soo; Kim, Chul‐Ho; Oh, Baek-Rock

doi:10.3390/catal11101139

Cited by 9 publications

(5 citation statements)

References 43 publications

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“…However, L. reuteri used less glycerol when incubated with 600 versus 300 mM glycerol, as observed previously, , possibly due to substrate inhibition or osmotic pressure on the cells. As compared to FUA3400, SD2112 produced more acrolein at all glycerol concentrations, that is, approximately 2-fold more from 300 versus 600 mM glycerol.…”

Section: Resultssupporting

confidence: 72%

Pathogenic and Commensal Gut Bacteria Harboring Glycerol/Diol Dehydratase Metabolize Glycerol and Produce DNA-Reactive Acrolein

Garcia

Hurley

Marastoni

et al. 2022

Chem. Res. Toxicol.

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Bacteria harboring glycerol/diol dehydratase (GDH) encoded by the genes pduCDE metabolize glycerol and release acrolein during growth. Acrolein has antimicrobial activity, and exposure of human cells to acrolein gives rise to toxic and mutagenic responses. These biological responses are related to acrolein’s high reactivity as a chemical electrophile that can covalently bind to cellular nucleophiles including DNA and proteins. Various food microbes and gut commensals transform glycerol to acrolein, but there is no direct evidence available for bacterial glycerol metabolism giving rise to DNA adducts. Moreover, it is unknown whether pathogens, such as Salmonella Typhymurium, catalyze this transformation. We assessed, therefore, acrolein formation by four GDH-competent strains of S. Typhymurium grown under either aerobic or anaerobic conditions in the presence of 50 mM glycerol. On the basis of analytical derivatization with a heterocyclic amine, all wild-type strains were observed to produce acrolein, but to different extents, and acrolein production was not detected in fermentations of a pduC-deficient mutant strain. Furthermore, we found that, in the presence of calf thymus DNA, acrolein-DNA adducts were formed as a result of bacterial glycerol metabolism by two strains of Limosilactobacillus reuteri, but not a pduCDE mutant strain. The quantification of the resulting adducts with increasing levels of glycerol up to 600 mM led to the production of up to 1.5 mM acrolein and 3600 acrolein-DNA adducts per 108 nucleosides in a model system. These results suggest that GDH-competent food microbes, gut commensals, and pathogens alike have the capacity to produce acrolein from glycerol. Further, the acrolein production can lead to DNA adduct formation, but requires high glycerol concentrations that are not available in the human gut.

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Section: Resultssupporting

confidence: 72%

Pathogenic and Commensal Gut Bacteria Harboring Glycerol/Diol Dehydratase Metabolize Glycerol and Produce DNA-Reactive Acrolein

Garcia

Hurley

Marastoni

et al. 2022

Chem. Res. Toxicol.

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“…All DNA and protein techniques were carried out following the standard molecular biological protocols. 3-HPA was provided by Korea Research Institute of Bioscience (KRIBB) and used for standard curve using HPLC [ 54 ].…”

Section: Methodsmentioning

confidence: 99%

In Vitro One-Pot 3-Hydroxypropanal Production from Cheap C1 and C2 Compounds

Seo

Yeom

2022

IJMS

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One- or two-carbon (C1 or C2) compounds have been considered attractive substrates because they are inexpensive and abundant. Methanol and ethanol are representative C1 and C2 compounds, which can be used as bio-renewable platform feedstocks for the biotechnological production of value-added natural chemicals. Methanol-derived formaldehyde and ethanol-derived acetaldehyde can be converted to 3-hydroxypropanal (3-HPA) via aldol condensation. 3-HPA is used in food preservation and as a precursor for 3-hydroxypropionic acid and 1,3-propanediol that are starting materials for manufacturing biocompatible plastic and polytrimethylene terephthalate. In this study, 3-HPA was biosynthesized from formaldehyde and acetaldehyde using deoxyribose-5-phosphate aldolase from Thermotoga maritima (DERATma) and cloned and expressed in Escherichia coli for 3-HPA production. Under optimum conditions, DERATma produced 7 mM 3-HPA from 25 mM substrate (formaldehyde and acetaldehyde) for 60 min with 520 mg/L/h productivity. To demonstrate the one-pot 3-HPA production from methanol and ethanol, we used methanol dehydrogenase from Lysinibacillus xylanilyticus (MDHLx) and DERATma. One-pot 3-HPA production via aldol condensation of formaldehyde and acetaldehyde from methanol and ethanol, respectively, was investigated under optimized reaction conditions. This is the first report on 3-HPA production from inexpensive alcohol substrates (methanol and ethanol) by cascade reaction using DERATma and MDHLx.

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“…Moreover, repeated freeze–thaw cycles (−20/4 °C) caused a slow decrease in 3-HPA with every cycle [ 23 ]. In addition, the degradation of 3-HPA to acrolein in aqueous solution was greater at high temperatures (37 °C and 40 °C), while there was very little degradation at 4 °C for 4 weeks [ 45 ]. Similarly, IC-PAD analysis suggested that 3-HPA/acrolein did not interconvert at low temperature and acidic pH [ 42 ].…”

Section: Stabilitymentioning

confidence: 99%

Application of the Reuterin System as Food Preservative or Health-Promoting Agent: A Critical Review

Sun

et al. 2022

Foods

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The reuterin system is a complex multi-component antimicrobial system produced by Limosilactobacillus reuteri by metabolizing glycerol. The system mainly includes 3-hydroxypropionaldehyde (3-HPA, reuterin), 3-HPA dimer, 3-HPA hydrate, acrolein and 3-hydroxypropionic acid, and has great potential to be applied in the food and medical industries due to its functional versatility. It has been reported that the reuterin system possesses regulation of intestinal flora and anti-infection, anti-inflammatory and anti-cancer activities. Typically, the reuterin system exerts strong broad-spectrum antimicrobial properties. However, the antimicrobial mechanism of the reuterin system remains unclear, and its toxicity is still controversial. This paper presents an updated review on the biosynthesis, composition, biological production, antimicrobial mechanisms, stability, toxicity and potential applications of the reuterin system. Challenges and opportunities of the use of the reuterin system as a food preservative or health-promoting agent are also discussed. The present work will allow researchers to accelerate their studies toward solving critical challenges obstructing industrial applications of the reuterin system.

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The Biocatalytic Production of 3-Hydroxypropionaldehyde and Evaluation of Its Stability

Cited by 9 publications

References 43 publications

Pathogenic and Commensal Gut Bacteria Harboring Glycerol/Diol Dehydratase Metabolize Glycerol and Produce DNA-Reactive Acrolein

Pathogenic and Commensal Gut Bacteria Harboring Glycerol/Diol Dehydratase Metabolize Glycerol and Produce DNA-Reactive Acrolein

In Vitro One-Pot 3-Hydroxypropanal Production from Cheap C1 and C2 Compounds

Application of the Reuterin System as Food Preservative or Health-Promoting Agent: A Critical Review

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