Pyridoxal

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Pyridoxal
Pyridoxal.png
Idealised skeletal formula
Pyridoxal-from-xtal-3D-bs-17.png
Ball-and-stick model based on the crystal structure. [1] [2] Note that the acidic phenol group has donated a proton to the basic pyridine group to form a zwitterion, and the hydroxymethyl group has reacted with the aldehyde group to form a hemiacetal.
Names
Preferred IUPAC name
3-Hydroxy-5-(hydroxymethyl)-2-methylpyridine-4-carbaldehyde
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.000.573 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
UNII
  • InChI=1S/C8H9NO3/c1-5-8(12)7(4-11)6(3-10)2-9-5/h2,4,10,12H,3H2,1H3 Yes check.svgY
    Key: RADKZDMFGJYCBB-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C8H9NO3/c1-5-8(12)7(4-11)6(3-10)2-9-5/h2,4,10,12H,3H2,1H3
    Key: RADKZDMFGJYCBB-UHFFFAOYAP
  • O=Cc1c(O)c(C)ncc1CO
Properties
C8H9NO3
Molar mass 167.16 g/mol
Melting point 165 °C (329 °F; 438 K) (decomposes)
Related compounds
Related arylformaldehydes
Damnacanthal

Gossypol

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Pyridoxal is one form of vitamin B6.

Some medically relevant bacteria, such as those in the genera Granulicatella and Abiotrophia, require pyridoxal for growth. This nutritional requirement can lead to the culture phenomenon of satellite growth. In in vitro culture, these pyridoxal-dependent bacteria may only grow in areas surrounding colonies of bacteria from other genera ("satellitism") that are capable of producing pyridoxal.

Pyridoxal is involved in what is believed to be the most ancient reaction of aerobic metabolism on Earth, about 2.9 billion years ago, a forerunner of the Great Oxidation Event. [3]

See also

Related Research Articles

An anaerobic organism or anaerobe is any organism that does not require molecular oxygen for growth. It may react negatively or even die if free oxygen is present. In contrast, an aerobic organism (aerobe) is an organism that requires an oxygenated environment. Anaerobes may be unicellular or multicellular. Most fungi are obligate aerobes, requiring oxygen to survive. However, some species, such as the Chytridiomycota that reside in the rumen of cattle, are obligate anaerobes; for these species, anaerobic respiration is used because oxygen will disrupt their metabolism or kill them. Deep waters of the ocean are a common anoxic environment.

<span class="mw-page-title-main">Green sulfur bacteria</span> Family of bacteria

The green sulfur bacteria are a phylum, Chlorobiota, of obligately anaerobic photoautotrophic bacteria that metabolize sulfur.

<span class="mw-page-title-main">Facultative anaerobic organism</span> Beings that can respire with and without oxygen

A facultative anaerobic organism is an organism that makes ATP by aerobic respiration if oxygen is present, but is capable of switching to fermentation if oxygen is absent.

<span class="mw-page-title-main">Obligate anaerobe</span> Microorganism killed by normal atmospheric levels of oxygen

Obligate anaerobes are microorganisms killed by normal atmospheric concentrations of oxygen (20.95% O2). Oxygen tolerance varies between species, with some species capable of surviving in up to 8% oxygen, while others lose viability in environments with an oxygen concentration greater than 0.5%.

<span class="mw-page-title-main">Pyridoxal phosphate</span> Active form of vitamin B6

Pyridoxal phosphate (PLP, pyridoxal 5'-phosphate, P5P), the active form of vitamin B6, is a coenzyme in a variety of enzymatic reactions. The International Union of Biochemistry and Molecular Biology has catalogued more than 140 PLP-dependent activities, corresponding to ~4% of all classified activities. The versatility of PLP arises from its ability to covalently bind the substrate, and then to act as an electrophilic catalyst, thereby stabilizing different types of carbanionic reaction intermediates.

<span class="mw-page-title-main">Purple bacteria</span> Group of phototrophic bacteria

Purple bacteria or purple photosynthetic bacteria are Gram-negative proteobacteria that are phototrophic, capable of producing their own food via photosynthesis. They are pigmented with bacteriochlorophyll a or b, together with various carotenoids, which give them colours ranging between purple, red, brown, and orange. They may be divided into two groups – purple sulfur bacteria and purple non-sulfur bacteria. Purple bacteria are anoxygenic phototrophs widely spread in nature, but especially in aquatic environments, where there are anoxic conditions that favor the synthesis of their pigments.

<span class="mw-page-title-main">Sulfate-reducing microorganism</span> Microorganisms that "breathe" sulfates

Sulfate-reducing microorganisms (SRM) or sulfate-reducing prokaryotes (SRP) are a group composed of sulfate-reducing bacteria (SRB) and sulfate-reducing archaea (SRA), both of which can perform anaerobic respiration utilizing sulfate (SO2−
4
) as terminal electron acceptor, reducing it to hydrogen sulfide (H2S). Therefore, these sulfidogenic microorganisms "breathe" sulfate rather than molecular oxygen (O2), which is the terminal electron acceptor reduced to water (H2O) in aerobic respiration.

<span class="mw-page-title-main">Lactic acid bacteria</span> Order of bacteria

Lactobacillales are an order of gram-positive, low-GC, acid-tolerant, generally nonsporulating, nonrespiring, either rod-shaped (bacilli) or spherical (cocci) bacteria that share common metabolic and physiological characteristics. These bacteria, usually found in decomposing plants and milk products, produce lactic acid as the major metabolic end product of carbohydrate fermentation, giving them the common name lactic acid bacteria (LAB).

<i>Beggiatoa</i> Genus of bacteria

Beggiatoa is a genus of Gammaproteobacteria belonging to the order Thiotrichales, in the Pseudomonadota phylum. This genus was one of the first bacteria discovered by Ukrainian botanist Sergei Winogradsky. During his research in Anton de Bary's laboratory of botany in 1887, he found that Beggiatoa oxidized hydrogen sulfide (H2S) as an energy source, forming intracellular sulfur droplets, with oxygen as the terminal electron acceptor and CO2 used as a carbon source. Winogradsky named it in honor of the Italian doctor and botanist Francesco Secondo Beggiato (1806 - 1883), from Venice. Winogradsky referred to this form of metabolism as "inorgoxidation" (oxidation of inorganic compounds), today called chemolithotrophy. These organisms live in sulfur-rich environments such as soil, both marine and freshwater, in the deep sea hydrothermal vents and in polluted marine environments. The finding represented the first discovery of lithotrophy. Two species of Beggiatoa have been formally described: the type species Beggiatoa alba and Beggiatoa leptomitoformis, the latter of which was only published in 2017. This colorless and filamentous bacterium, sometimes in association with other sulfur bacteria (for example the genus Thiothrix), can be arranged in biofilm visible to the naked eye formed by a very long white filamentous mat, the white color is due to the stored sulfur. Species of Beggiatoa have cells up to 200 µm in diameter and they are one of the largest prokaryotes on Earth.

Microbial metabolism is the means by which a microbe obtains the energy and nutrients it needs to live and reproduce. Microbes use many different types of metabolic strategies and species can often be differentiated from each other based on metabolic characteristics. The specific metabolic properties of a microbe are the major factors in determining that microbe's ecological niche, and often allow for that microbe to be useful in industrial processes or responsible for biogeochemical cycles.

Leuconostoc mesenteroides is a species of lactic acid bacteria associated with fermentation, under conditions of salinity and low temperatures. In some cases of vegetable and food storage, it was associated with pathogenicity. L. mesenteroides is approximately 0.5-0.7 µm in diameter and has a length of 0.7-1.2 µm, producing small grayish colonies that are typically less than 1.0 mm in diameter. It is facultatively anaerobic, Gram-positive, non-motile, non-sporogenous, and spherical. It often forms lenticular coccoid cells in pairs and chains, however, it can occasionally form short rods with rounded ends in long chains, as its shape can differ depending on what media the species is grown on. L. mesenteroides grows best at 30 °C, but can survive in temperatures ranging from 10 °C to 30 °C. Its optimum pH is 5.5, but can still show growth in pH of 4.5-7.0.

Hydrogen-oxidizing bacteria are a group of facultative autotrophs that can use hydrogen as an electron donor. They can be divided into aerobes and anaerobes. The former use hydrogen as an electron donor and oxygen as an acceptor while the latter use sulphate or nitrogen dioxide as electron acceptors. Species of both types have been isolated from a variety of environments, including fresh waters, sediments, soils, activated sludge, hot springs, hydrothermal vents and percolating water.

<span class="mw-page-title-main">Flavobacteriia</span> Class of bacteria

The class Flavobacteriia is composed of a single class of environmental bacteria. It contains the family Flavobacteriaceae, which is the largest family in the phylum Bacteroidota. This class is widely distributed in soil, fresh, and seawater habitats. The name is often spelt Flavobacteria, but was officially named Flavobacteriia in 2012.

<span class="mw-page-title-main">Alanine racemase</span>

In enzymology, an alanine racemase is an enzyme that catalyzes the chemical reaction

<span class="mw-page-title-main">Cystathionine beta-lyase</span> Enzyme

Cystathionine beta-lyase, also commonly referred to as CBL or β-cystathionase, is an enzyme that primarily catalyzes the following α,β-elimination reaction

<span class="mw-page-title-main">Threonine ammonia-lyase</span>

Threonine ammonia-lyase (EC 4.3.1.19, systematic name L-threonine ammonia-lyase (2-oxobutanoate-forming), also commonly referred to as threonine deaminase or threonine dehydratase, is an enzyme responsible for catalyzing the conversion of L-threonine into α-ketobutyrate and ammonia:

<span class="mw-page-title-main">Arginine decarboxylase</span>

The enzyme Acid-Induced Arginine Decarboxylase (AdiA), also commonly referred to as arginine decarboxylase, catalyzes the conversion of L-arginine into agmatine and carbon dioxide. The process consumes a proton in the decarboxylation and employs a pyridoxal-5'-phosphate (PLP) cofactor, similar to other enzymes involved in amino acid metabolism, such as ornithine decarboxylase and glutamine decarboxylase. It is found in bacteria and virus, though most research has so far focused on forms of the enzyme in bacteria. During the AdiA catalyzed decarboxylation of arginine, the necessary proton is consumed from the cell cytoplasm which helps to prevent the over-accumulation of protons inside the cell and serves to increase the intracellular pH. Arginine decarboxylase is part of an enzymatic system in Escherichia coli, Salmonella Typhimurium, and methane-producing bacteria Methanococcus jannaschii that makes these organisms acid resistant and allows them to survive under highly acidic medium.

Ultramicrobacteria are bacteria that are smaller than 0.1 μm3 under all growth conditions. This term was coined in 1981, describing cocci in seawater that were less than 0.3 μm in diameter. Ultramicrobacteria have also been recovered from soil and appear to be a mixture of Gram-positive, Gram-negative and cell-wall-lacking species. Ultramicrobacteria possess a relatively high surface-area-to-volume ratio due to their small size, which aids in growth under oligotrophic conditions. The relatively small size of ultramicrobacteria also enables parasitism of larger organisms; some ultramicrobacteria have been observed to be obligate or facultative parasites of various eukaryotes and prokaryotes. One factor allowing ultramicrobacteria to achieve their small size seems to be genome minimization such as in the case of the ultramicrobacterium P. ubique whose small 1.3 Mb genome is seemingly devoid of extraneous genetic elements like non-coding DNA, transposons, extrachromosomal elements etc. However, genomic data from ultramicrobacteria is lacking since the study of ultramicrobacteria, like many other prokaryotes, is hindered by difficulties in cultivating them.

Diauxic growth, diauxie or diphasic growth is any cell growth characterized by cellular growth in two phases. Diauxic growth, meaning double growth, is caused by the presence of two sugars on a culture growth media, one of which is easier for the target bacterium to metabolize. The preferred sugar is consumed first, which leads to rapid growth, followed by a lag phase. During the lag phase the cellular machinery used to metabolize the second sugar is activated and subsequently the second sugar is metabolized.

Congregibacter litoralis KT71 is a gram-negative Gammaproteobacteria part of the NOR5/OM60 Clade discovered in seawater from Heligoland, an island in the North Sea by H. Eilers from the Max Planck Institute for Microbiology. C. litoralis KT71 is described as a pleomorphic bacterium and has a size of 2 x 0.5 μm. When grown in culture, C. litoralis KT71 has a generation time of 4.5 hours and prefers to grow on complex substrates where the sole carbon source is undefined, though it can utilize some sole carbon sources because they are most likely used by the organism for its central metabolism.

References

  1. "CSD Entry: BIHKEI01". Cambridge Structural Database: Access Structures. Cambridge Crystallographic Data Centre. 1985. Retrieved 2023-11-04.
  2. MacLaurin, C. L.; Richardson, M. F. (1985). "Pyridoxal, C8H9NO3, and pyridoxamine dihydrate, C8H12N2O2.2H2O". Acta Crystallogr. C . 41 (2): 261–263. Bibcode:1985AcCrC..41..261M. doi:10.1107/S0108270185003547.
  3. "Protein Domain Structure Uncovers the Origin of Aerobic Metabolism and the Rise of Planetary Oxygen", Gustavo Caetano-Anolles et al., published in Structure; paper available from University of Illinois News Bureau, 2012.