Alternative pathway for the formation of 4,5-dihydroxy-2,3-pentanedione, the proposed precursor of 4-hydroxy-5-methyl-3(2H)-furanone as well as autoinducer-2, and its detection as natural constituent of tomato fruit

Hauck, Tobias; Hübner, Yvonne; Brühlmann, Fredi; Schwab, Wilfried

doi:10.1016/j.bbagen.2003.08.002

Cited by 34 publications

(48 citation statements)

References 37 publications

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“…With a k = 0.015 M -1 h -1 in a reaction with NAcLys, the Maillard activity of dR5P is considerably less (factor of [10][11][12][13][14][15][16][17][18][19][20] than that of R5P. This is expected for two reasons.…”

Section: Rate Of Sugar Consumptionmentioning

confidence: 96%

“…10 In comparison, ribulose 5-phosphate has an absorbance maximum of 280 nm and hydroxymethylfuranone (4-hydroxyl-5-methyl-3(2H)-furanone, HMF), a spontaneous product of ribulose 5-phosphate degradation, has a reported absorbance maximum of 285 nm. 10 The lack of significant 310-320 nm absorbance indicates the reaction series is deviating from the normal progression through the α-dicarbonyl forms or that it is rapidly transitioning through these dicarbonyl intermediates. For example, Asn has been reported to react with glucose in an acrylamide-producing, decarboxylation reaction that ultimately results in a fructosamine product.…”

Section: Absorbance Changesmentioning

confidence: 99%

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The multiple Maillard reactions of ribose and deoxyribose sugars and sugar phosphates

Munanairi

O’Banion

Gamble

et al. 2007

Carbohydrate Research

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Section: Rate Of Sugar Consumptionmentioning

confidence: 96%

Section: Absorbance Changesmentioning

confidence: 99%

The multiple Maillard reactions of ribose and deoxyribose sugars and sugar phosphates

Munanairi

O’Banion

Gamble

et al. 2007

Carbohydrate Research

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“…LuxS acts by cleaving SRH to produce homocysteine and DPD. DPD is thought to give rise to AI-2 by spontaneous cyclization and reaction with borate (9,42 (23), which can be synthesized from D-ribose-5-phosphate. The enzyme responsible for this conversion is ribose-5-phosphate isomerase (21).…”

Section: Discussionmentioning

confidence: 99%

Microarray Analysis of Quorum-Sensing-Regulated Genes inPorphyromonas gingivalis

2005

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Quorum sensing is a phenomenon defined as gene regulation in response to cell density that regulates various functions in bacteria. The periodontopathogen Porphyromonas gingivalis possesses a luxS gene homologue that may encode a quorum-sensing system. In order to identify genes of P. gingivalis that are regulated by luxS, gene expression analysis was done using microarrays and RNA samples from the W83 wild-type strain and an isogenic luxS mutant, LY2001. The results indicated that 17 open reading frames (ORFs) in LY2001 are upregulated and two are downregulated. Real-time PCR was done to confirm the microarray results. Among the upregulated ORFs is a group of stress-related genes, including htrA, clpB, groEL, dnaK, and the F subunit of alkyl hydroperoxide reductase. This suggested that luxS is involved in stress gene regulation in P. gingivalis. Stress response experiments, including high-temperature survival, resistance to hydrogen peroxide (H 2 O 2 ), and survival during exposure to low and high pH, were performed on the P. gingivalis wild-type and LY2001 strains. LY2001 had a significantly higher survival rate than did W83 when stressed at 50°C. No difference was found at pH 5, but LY2001 had increased survival compared to W83 at pH 9. LY2001 also survived better than W83 when stressed with 0.35 mM H 2 O 2 . These results suggest that luxS might be involved in promoting survival of P. gingivalis in the host by regulating its response to host-induced stresses such as temperature, H 2 O 2 , and pH.

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“…1B) (29,30). Addition of this diamine to the aqueous solution resulted in the disappearance of DPD and its equilibrium products, and led to the formation a single, stable quinoxaline derivative 6 through a Maillard reaction, with only a few other signals remaining in the spectrum.…”

Section: Characterization Of Dpdmentioning

confidence: 99%

Chemical Synthesis of (S)-4,5-Dihydroxy-2,3-pentanedione, a Bacterial Signal Molecule Precursor, and Validation of Its Activity in Salmonella typhimurium

Keersmaecker¹,

Várszegi

Boxel³

et al. 2005

Journal of Biological Chemistry

129

120

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We describe an original, short, and convenient chemical synthesis of enantiopure (S)-4,5-dihydroxy-2,3-pentanedione (DPD), starting from commercial methyl (S)-(؊)-2,2-dimethyl-1,3-dioxolane-4-carboxylate. DPD is the precursor of autoinducer (AI)-2, the proposed signal for bacterial interspecies communication. AI-2 is synthesized by many bacterial species in three enzymatic steps. The last step, a LuxS-catalyzed reaction, leads to the formation of DPD, which spontaneously cyclizes into AI-2. AI-2-like activity of the synthesized molecule was ascertained by the Vibrio harveyi bioassay. To further validate the biological activity of synthetic DPD and to explore its potential in studying DPD (AI-2)-mediated signaling, a Salmonella typhimurium luxS mutant was constructed. Expression of the AI-2 regulated lsr operon can be rescued in this luxS mutant by addition of synthetic DPD or genetic complementation. Biofilm formation by S. typhimurium has been reported to be defective in a luxS mutant, and this was confirmed in this study to test DPD for chemical complementation. However, biofilm formation of the luxS mutant cannot be restored by addition of DPD. In contrast, introduction of luxS under control of its own promoter complemented biofilm formation. Further results demonstrated that biofilm formation of the luxS mutant cannot be restored with luxS under control of the strong nptII promoter. This indicates that altering the intrinsic promoter activity of luxS affects Salmonella biofilm formation. Conclusively, we synthesized biologically active DPD. Using this chemical compound in combination with genetic approaches opens new avenues in studying AI-2-mediated signaling.

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Alternative pathway for the formation of 4,5-dihydroxy-2,3-pentanedione, the proposed precursor of 4-hydroxy-5-methyl-3(2H)-furanone as well as autoinducer-2, and its detection as natural constituent of tomato fruit

Cited by 34 publications

References 37 publications

The multiple Maillard reactions of ribose and deoxyribose sugars and sugar phosphates

The multiple Maillard reactions of ribose and deoxyribose sugars and sugar phosphates

Microarray Analysis of Quorum-Sensing-Regulated Genes inPorphyromonas gingivalis

Chemical Synthesis of (S)-4,5-Dihydroxy-2,3-pentanedione, a Bacterial Signal Molecule Precursor, and Validation of Its Activity in Salmonella typhimurium

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