4,5-Dihydroxy-2,3-pentanedione

Last updated
4,5-Dihydroxy-2,3-pentanedione
Nominal S-DPD.png
Names
Preferred IUPAC name
4,5-Dihydroxypentane-2,3-dione
Other names
1-Deoxypento-2,4-diulose
1-Deoxypentosone
Dihydroxy-2,3-pentanedione
DPD
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
UNII
  • InChI=1S/C5H8O4/c1-3(7)5(9)4(8)2-6/h4,6,8H,2H2,1H3
    Key: UYTRITJAZOPLCZ-UHFFFAOYSA-N
  • CC(=O)C(=O)C(CO)O
Properties
C5H8O4
Molar mass 132.115 g·mol−1
AppearanceColorless
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

4,5-Dihydroxy-2,3-pentanedione (DPD) is an organic compound that occurs naturally but exists as several related structures. The idealized formula for this species is CH3C(O)C(O)CH(OH)CH2OH, but it is known to exist as several other forms resulting from cyclization. It is not stable at room temperature as a pure material, which has further complicated its analysis. The (S)-stereoisomer occurs naturally. It is typically hydrated, i.e., one keto group has added water to give the geminal diol.

DPD is produced by degradation of S-adenosylhomocysteine by the action of the enzyme S-ribosylhomocysteinase. [1] The compound probably does not exist as depicted above, but as an equilibrium mixture of three hydrates.

Hydrated derivatives of dihydroxypentanedione. TPDhydratesJanda.png
Hydrated derivatives of dihydroxypentanedione.

DPD is a precursor to borate diester, which is known as autoinducer-2 (AI-2). AI-2 is a signaling molecules found in quorum sensing. It is produced and recognized by many Gram-negative and Gram-positive bacteria. [3] [4] AI-2 is synthesized by the reaction of DPD with boric acid [5] and is recognized by the two-component sensor kinase LuxPQ in Vibrionaceae.

Related Research Articles

Bonnie Bassler American molecular biologist

Bonnie Lynn Bassler is an American molecular biologist; the Squibb Professor in Molecular Biology and chair of the Department of Molecular Biology at Princeton University; and a Howard Hughes Medical Institute Investigator. She has researched cell-to-cell chemical communication in bacteria and discovered key insights into the mechanism by which bacteria communicate, known as quorum sensing. She has contributed to the idea that disruption of chemical signaling can be used as an antimicrobial therapy.

In biology, quorum sensing or quorum signalling (QS) is the ability to detect and respond to cell population density by gene regulation. As one example, QS enables bacteria to restrict the expression of specific genes to the high cell densities at which the resulting phenotypes will be most beneficial. Many species of bacteria use quorum sensing to coordinate gene expression according to the density of their local population. In a similar fashion, some social insects use quorum sensing to determine where to nest. Quorum sensing may also be useful for cancer cell communications.

<i>Aliivibrio fischeri</i> Species of bacterium

Aliivibrio fischeri is a Gram-negative, rod-shaped bacterium found globally in marine environments. This species has bioluminescent properties, and is found predominantly in symbiosis with various marine animals, such as the Hawaiian bobtail squid. It is heterotrophic, oxidase-positive, and motile by means of a single polar flagella. Free-living A. fischeri cells survive on decaying organic matter. The bacterium is a key research organism for examination of microbial bioluminescence, quorum sensing, and bacterial-animal symbiosis. It is named after Bernhard Fischer, a German microbiologist.

<i>Vibrio harveyi</i> Species of bacterium

Vibrio harveyi is a Gram-negative, bioluminescent, marine bacterium in the genus Vibrio. V. harveyi is rod-shaped, motile, facultatively anaerobic, halophilic, and competent for both fermentative and respiratory metabolism. It does not grow below 4 °C. V. harveyi can be found free-swimming in tropical marine waters, commensally in the gut microflora of marine animals, and as both a primary and opportunistic pathogen of marine animals, including Gorgonian corals, oysters, prawns, lobsters, the common snook, barramundi, turbot, milkfish, and seahorses. It is responsible for luminous vibriosis, a disease that affects commercially farmed penaeid prawns. Additionally, based on samples taken by ocean-going ships, V. harveyi is thought to be the cause of the milky seas effect, in which, during the night, a uniform blue glow is emitted from the seawater. Some glows can cover nearly 6,000 sq mi (16,000 km2).

In biology, cell signaling or cell communication is the ability of a cell to receive, process, and transmit signals with its environment and with itself. Cell signaling is a fundamental property of all cellular life in prokaryotes and eukaryotes. Signals that originate from outside a cell can be physical agents like mechanical pressure, voltage, temperature, light, or chemical signals. Chemical signals can be hydrophobic or hydrophilic. Cell signaling can occur over short or long distances, and as a result can be classified as autocrine, juxtacrine, intracrine, paracrine, or endocrine. Signaling molecules can be synthesized from various biosynthetic pathways and released through passive or active transports, or even from cell damage.

Bacteria Domain of micro-organisms

Bacteria are ubiquitous, mostly free-living organisms often consisting of one biological cell. They constitute a large domain of prokaryotic microorganisms. Typically a few micrometres in length, bacteria were among the first life forms to appear on Earth, and are present in most of its habitats. Bacteria inhabit soil, water, acidic hot springs, radioactive waste, and the deep biosphere of Earth's crust. Bacteria are vital in many stages of the nutrient cycle by recycling nutrients such as the fixation of nitrogen from the atmosphere. The nutrient cycle includes the decomposition of dead bodies; bacteria are responsible for the putrefaction stage in this process. In the biological communities surrounding hydrothermal vents and cold seeps, extremophile bacteria provide the nutrients needed to sustain life by converting dissolved compounds, such as hydrogen sulphide and methane, to energy. Bacteria also live in symbiotic and parasitic relationships with plants and animals. Most bacteria have not been characterised and there are many species that cannot be grown in the laboratory. The study of bacteria is known as bacteriology, a branch of microbiology.

Qrr RNA Biological molecule

Qrr is a non-coding RNA that is thought to be involved in the regulation of quorum sensing in Vibrio species. It is believed that these RNAs, guided by a protein, Hfq, can mediate the destabilisation of the quorum-sensing master regulators LuxR/HapR/VanT mRNAs.

<i>Roseobacter</i> Genus of bacteria

In taxonomy, Roseobacter is a genus of the Rhodobacteraceae. The Roseobacter clade falls within the {alpha}-3 subclass of the class Alphaproteobacteria. The first strain descriptions appeared in 1991 which described members Roseobacterlitoralis and Roseobacterdenitrificans, both pink-pigmented bacteriochlorophyll a-producing strains isolated from marine algae. The role members of the Roseobacter lineage play in marine biogeochemical cycles and climate change cannot be overestimated. Roseobacters make up 25% of coastal marine bacteria and members of this lineage process a significant portion of the total carbon in the marine environment. Roseobacter clade plays an important role in global carbon and sulphur cycles. It can also degrade aromatic compounds, uptake trace metal, and form symbiotic relationship. In term of its application, Roseobacter clade produces bioactive compounds, has been used widely in aquaculture and quorum sensing.

S-ribosylhomocysteine lyase

The enzyme S-ribosylhomocysteine lyase catalyzes the reaction

Autoinducers are signaling molecules that are produced in response to changes in cell-population density. As the density of quorum sensing bacterial cells increases so does the concentration of the autoinducer. Detection of signal molecules by bacteria acts as stimulation which leads to altered gene expression once the minimal threshold is reached. Quorum sensing is a phenomenon that allows both Gram-negative and Gram-positive bacteria to sense one another and to regulate a wide variety of physiological activities. Such activities include symbiosis, virulence, motility, antibiotic production, and biofilm formation. Autoinducers come in a number of different forms depending on the species, but the effect that they have is similar in many cases. Autoinducers allow bacteria to communicate both within and between different species. This communication alters gene expression and allows bacteria to mount coordinated responses to their environments, in a manner that is comparable to behavior and signaling in higher organisms. Not surprisingly, it has been suggested that quorum sensing may have been an important evolutionary milestone that ultimately gave rise to multicellular life forms.

Lactonase

Lactonase (EC 3.1.1.81, acyl-homoserine lactonase; systematic name N-acyl-L-homoserine-lactone lactonohydrolase) is a metalloenzyme, produced by certain species of bacteria, which targets and inactivates acylated homoserine lactones (AHLs). It catalyzes the reaction

Autoinducer-2 Chemical compound

Autoinducer-2 (AI-2), a furanosyl borate diester or tetrahydroxy furan, is a member of a family of signaling molecules used in quorum sensing. AI-2 is one of only a few known biomolecules incorporating boron. First identified in the marine bacterium Vibrio harveyi, AI-2 is produced and recognized by many Gram-negative and Gram-positive bacteria. AI-2 arises by the reaction of 4,5-Dihydroxy-2,3-pentanedione, which is produced enzymatically with boric acid, and is recognized by the two-component sensor kinase LuxPQ in Vibrionaceae.

Bacterial small RNAs (sRNA) are small RNAs produced by bacteria; they are 50- to 500-nucleotide non-coding RNA molecules, highly structured and containing several stem-loops. Numerous sRNAs have been identified using both computational analysis and laboratory-based techniques such as Northern blotting, microarrays and RNA-Seq in a number of bacterial species including Escherichia coli, the model pathogen Salmonella, the nitrogen-fixing alphaproteobacterium Sinorhizobium meliloti, marine cyanobacteria, Francisella tularensis, Streptococcus pyogenes, the pathogen Staphylococcus aureus, and the plant pathogen Xanthomonas oryzae pathovar oryzae. Bacterial sRNAs affect how genes are expressed within bacterial cells via interaction with mRNA or protein, and thus can affect a variety of bacterial functions like metabolism, virulence, environmental stress response, and structure.

LuxR-type DNA-binding HTH domain

In molecular biology, the LuxR-type DNA-binding HTH domain is a DNA-binding, helix-turn-helix (HTH) domain of about 65 amino acids. It is present in transcription regulators of the LuxR/FixJ family of response regulators. The domain is named after Vibrio fischeri luxR, a transcriptional activator for quorum-sensing control of luminescence. LuxR-type HTH domain proteins occur in a variety of organisms. The DNA-binding HTH domain is usually located in the C-terminal region of the protein; the N-terminal region often containing an autoinducer-binding domain or a response regulatory domain. Most luxR-type regulators act as transcription activators, but some can be repressors or have a dual role for different sites. LuxR-type HTH regulators control a wide variety of activities in various biological processes.

Interspecies quorum sensing is a type of quorum sensing in which bacteria send and receive signals to other species besides their own. This is accomplished by the secretion of signaling molecules which trigger a response in nearby bacteria at high enough concentrations. Once the molecule hits a certain concentration it triggers the transcription of certain genes such as virulence factors. It has been discovered that bacteria can not only interact via quorum sensing with members of their own species but that there is a kind of universal molecule that allows them to gather information about other species as well. This universal molecule is called autoinducer 2 or AI-2.

Bacterial morphological plasticity refers to changes in the shape and size that bacterial cells undergo when they encounter stressful environments. Although bacteria have evolved complex molecular strategies to maintain their shape, many are able to alter their shape as a survival strategy in response to protist predators, antibiotics, the immune response, and other threats.

Vibrio campbellii is a Gram-negative, curved rod-shaped, marine bacterium closely related to its sister species, Vibrio harveyi. It is an emerging pathogen in aquatic organisms.

Bioluminescent bacteria

Bioluminescent bacteria are light-producing bacteria that are predominantly present in sea water, marine sediments, the surface of decomposing fish and in the gut of marine animals. While not as common, bacterial bioluminescence is also found in terrestrial and freshwater bacteria. These bacteria may be free living or in symbiosis with animals such as the Hawaiian Bobtail squid or terrestrial nematodes. The host organisms provide these bacteria a safe home and sufficient nutrition. In exchange, the hosts use the light produced by the bacteria for camouflage, prey and/or mate attraction. Bioluminescent bacteria have evolved symbiotic relationships with other organisms in which both participants benefit close to equally. Another possible reason bacteria use luminescence reaction is for quorum sensing, an ability to regulate gene expression in response to bacterial cell density.

The type VI secretion system (T6SS) is molecular machine used by a wide range of Gram-negative bacterial species to transport effectors from the interior of a bacterial cell across the cellular envelope into an adjacent target cell. While often reported that the T6SS was discovered in 2006 by researchers studying the causative agent of cholera, Vibrio cholerae, the first study demonstrating that T6SS genes encode a protein export apparatus was actually published in 2004, in a study of protein secretion by the fish pathogen Edwardsiella tarda.

A phytobiome consists of a plant (phyto) situated in its specific ecological area (biome), including its environment and the associated communities of organisms which inhabit it. These organisms include all macro- and micro-organisms living in, on, or around the plant including bacteria, archaea, fungi, protists, insects, animals, and other plants. The environment includes the soil, air, and climate. Examples of ecological areas are fields, rangelands, forests. Knowledge of the interactions within a phytobiome can be used to create tools for agriculture, crop management, increased health, preservation, productivity, and sustainability of cropping and forest systems.

References

  1. Jinge Zhu, Eric Dizin, Xubo Hu, Anne-Sophie Wavreille, Junguk Park, Dehua Pei "S-Ribosylhomocysteinase (LuxS) Is a Mononuclear Iron Protein" Biochemistry, 2003, volume 42, pp 4717–4726. doi : 10.1021/bi034289j
  2. Roberta J. Worthington and Christian Melander "Deconvoluting Interspecies Bacterial Communication" Angew. Chem. Int. Ed. 2012, volume 51, 6314 – 6315. doi : 10.1002/anie.201202440
  3. Miller, Stephen T.; Xavier, Karina B.; Campagna, Shawn R.; Taga, Michiko E.; Semmelhack, Martin F.; Bassler, Bonnie L.; Hughson, Frederick M. (2004). "Salmonella typhimurium Recognizes a Chemically Distinct Form of the Bacterial Quorum-Sensing Signal AI-2". Molecular Cell . 15 (5): 677–687. doi: 10.1016/j.molcel.2004.07.020 . PMID   15350213.
  4. Miller, M. B.; Bassler, B. L. (2001). "Quorum sensing in bacteria". Annual Review of Microbiology . 55: 165–199. doi:10.1146/annurev.micro.55.1.165. PMID   11544353.
  5. "Chemistry - Queen Mary University of London".