188674-57-9

Usage

Uses

Used in Synthesis:
2,3-Pentanedione, 4,5-dihydroxy-, (R)(9CI) is used as a synthetic building block for the development of various chemical compounds. Its unique structure allows for the creation of a wide range of molecules with different properties and applications.
Used in Bioluminescence Research:
2,3-Pentanedione, 4,5-dihydroxy-, (R)(9CI) is used as a precursor in the synthesis of auto-inducers, which are signaling molecules involved in the regulation of bioluminescence in certain organisms. This application is particularly relevant in the field of biotechnology, where understanding and controlling bioluminescence can have significant implications for the development of new technologies and applications.
Used in Pharmaceutical Industry:
Although not explicitly mentioned in the provided materials, the compound's unique structure and chirality may make it a potential candidate for the development of new drugs or drug delivery systems. Further research and development in this area could lead to the discovery of novel therapeutic agents.

Upstream product

• 866249-99-2 3-(1,2-dihydroxy-ethyl)-but-3-en-2-one 
• 1203707-89-4 3-diazo-4,5-dihydroxypentan-2-one 
• 1314558-94-5 rac-1-[(tert-butyldimethylsilyl)oxy]pent-3-yn-2-ol 
• 133095-72-4 pent-3-yne-1,2-diol 
• 710324-27-9 1-(2-methoxy-[1,3]-dioxolan-4-yl)-propane-1,2-dione 
• 500596-40-7 (R)-pent-3-yne-1,2-diol 
• 710324-25-7 (R)-2,2-Dimethyl-4-prop-1-ynyl-[1,3]dioxolane 
• 848035-01-8 (S)-4,5-cyclohexylidenedioxy-2,3-pentanedione 
• 848035-08-5 (R)-4,5-cyclohexylidenedioxy-2,3-pentanedione 
• 643-71-0 D-glucosone 
• 710324-26-8 2-methoxy-4-(prop-1-ynyl)-[1,3]-dioxolane 
• 87-72-9 D-Xylose 
• 56-40-6 glycine 
• 866249-98-1 3-[2-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-ethyl]-but-3-en-2-one 

Relevant academic research and scientific papers

Pyrogallol and its analogs can antagonize bacterial quorum sensing in Vibrio harveyi

Bacteria can coordinate community-wide behaviors through quorum sensing, that is, the secretion and sensing of autoinducer (AI) molecules. Bacterial quorum sensing is implicated in the regulation of pathologically relevant events such as biofilm formation, bacterial virulence, and drug resistance. Inhibitors of bacterial quorum sensing could therefore be useful therapeutics. Herein we report for the first time the discovery of several pyrogallol compounds as single digit micromolar inhibitors of bacterial quorum sensing in Vibrio harveyi.

An expeditious synthesis of DPD and boron binding studies

(Chemical Equation Presented) A practical synthesis has been developed for DPD (4,5-dihydroxypentane-2,3-dione), an unstable small molecule that is proposed to be the source of universal signaling agents for quorum sensing in bacteria. The synthesis allows preparation of isotopically labeled DPD and ent-DPD as well as detailed studies of spontaneous binding to borate to give the unusual borate complex 6, the signal for marine bacteria such as Vibrio harveyi.

Inhibition of Pseudomonas aeruginosa quorum sensing by AI-2 analogs

Autoinducer-2 (AI-2) has been suggested to serve as a universal interspecies quorum sensing signaling molecule. We have synthesized a set of AI-2 analogs with small incremental changes in alkyl substitution on C-2 and evaluated them for their agonistic and antagonistic potential as quorum sensing (QS) attenuators in two different bacterial species: Pseudomonas aeruginosa and Vibrio harveyi. Unexpectedly, several of the analogs were found to function as synergistic QS agonists in V. harveyi, while two of these analogs inhibit QS in P. aeruginosa.

Ac2-DPD, the bis-(O)-acetylated derivative of 4,5-dihydroxy-2,3-pentanedione (DPD) is a convenient stable precursor of bacterial quorum sensing autoinducer AI-2

Ac2-DPD, the bis-(O)-acetylated derivative of 4,5-dihydroxy-2,3-pentanedione (DPD), was prepared both as a racemic mixture and in the optically active form found in naturally occurring DPD. It was shown to exhibit the same ability as DPD to induce bioluminescence in Vibrio Harveyi and β-galactosidase activity in Salmonella enterica Typhimurium, both Gram-negative bacteria. Likewise, it was also shown to inhibit biofilm formation in Gram-positive Bacillus cereus. The most likely hypothesis is that Ac2-DPD activity is due to the release of DPD by in situ hydrolysis of the ester groups. Importantly, by contrast with DPD, Ac2-DPD proved to be a stable compound which can be purified and stored.

Synthesis and biological validation of a ubiquitous quorum-sensing molecule

Chemical communication ("quorum sensing") amongst bacteria has been studied by the synthesis and study of enantiopure (R)-4,5-dihydroxy-2,3- pentanedione (DPD, see scheme). Bioactivity assays with DPD have shown that chelation of boron by the cyclic form of DPD appears to be essential for full induction of bioluminescence, which is an example of quorum-sensing-controlled behavior.

Synergistic Effect of a Thermal Reaction and Vacuum Dehydration on Improving Xylose-Phenylalanine Conversion to N-(1-Deoxy- d -xylulos-1-yl)-phenylalanine during an Aqueous Maillard Reaction

The synergistic effect of a thermal reaction and vacuum dehydration on the conversion of xylose (Xyl) and phenylalanine (Phe) to a Maillard-reaction intermediate (MRI) was researched. The yield of N-(1-deoxy-α-d-xylulos-1-yl)-phenylalanine was successfully improved and increased from 13.62 to 47.23% through the method combining a thermal reaction and vacuum dehydration. A dynamic process was involved in the transformation of Xyl and Phe (Xyl-Phe) to N-substituted d-xylosamine and in the transformation of N-substituted d-xylosamine to N-(1-deoxy-α-d-xylulos-1-yl)-phenylalanine during the initial stage of dehydration; then, only the transformation of N-substituted d-xylosamine to N-(1-deoxy-α-d-xylulos-1-yl)-phenylalanine occurred during the final stage. Furthermore, the MRI was prepared under optimized conditions (90 °C and pH 7.4), and the obtained MRI was characterized and confirmed by ESI mass spectrometry and NMR.

5-(2-Aminoethyl)dithio-2-nitrobenzoate as a more base-stable alternative to ellman's reagent

(Chemical Equation Presented) 5-(2-Aminoethyl)dithio-2-nitrobenzoate (ADNB) reacts with free thiols with kinetics similar to those of Ellman's reagent but has dramatically improved stability under alkaline conditions, making it an excellent alternative to Ellman's reagent for the quantitation of thiol contents and enzymatic assays under basic pH conditions.

N-(1-Deoxy- d -xylulos-1-yl)-glutathione: A Maillard Reaction Intermediate Predominating in Aqueous Glutathione-Xylose Systems by Simultaneous Dehydration-Reaction

The effect of simultaneous dehydration-reaction (SDR) on Amadori rearrangement product (ARP) N-(1-deoxy-d-xylulos-1-yl)-glutathione and its key degradation products, 3-deoxyxylosone (3-DX) and 1-deoxyxylosone (1-DX), were investigated in an aqueous glutathione-xylose (GSH-Xyl) system. The yield of ARP was increased to 67.98% by SDR compared with 8.44% by atmospheric thermal reaction at 80 °C. Reaction kinetics was applied to analyze the mechanism and characteristics of ARP formation and degradation under SDR. ARP formation and degradation rate was highly dependent on temperature, and the latter was more sensitive to temperature. By regulating the reaction conditions of temperature and pH, the ratio of ARP formation rate constant to its degradation rate constant could be controlled to achieve an efficient preparation of ARP from GSH-Xyl Maillard reaction through SDR.

Maillard Browning Inhibition by Ellagic Acid via Its Adduct Formation with the Amadori Rearrangement Product

The Maillard reaction performed under a stepwise increase of temperature was applied for researching the inhibition of Maillard browning caused by ellagic acid. Ellagic acid was found effective for the inhibition of melanoidin formation in the xylose-glycine Maillard reaction but depended on its dosage and the point of time it was added in the reaction system. The lightest color of the Maillard reaction products was observed when ellagic acid was added at the 90th min, which was the point of time when the Amadori rearrangement product (ARP) developed the most. LC-ESI-MS/MS analysis results showed a significant tendency of the ellagic acid hydrolysis product to react with the predominant intermediate ARP to yield an adduct. The adduct stabilized the ARP and delayed its decomposition and inhibited the downstream reactions toward browning. After the ARP was depleted, ellagic acid also showed an effect on scavenging some short-chain dicarbonyls which contributed to the inhibition of Maillard browning.

Ozonolysis of Alkynes - A Flexible Route to Alpha-Diketones: Synthesis of AI-2

A mild procedure for the low-temperature conversion of alkynes to diketones has been developed and employed in the synthesis of AI-2.