Adenosine thiamine diphosphate

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Adenosine thiamine diphosphate
Adenosine Thiamine pyrophosphate.svg
Names
Systematic IUPAC name
(22R,23S,24R,25R)-16,134-Diamino-23,24,5,7-tetrahydroxy-114,132-dimethyl-5,7-dioxo-4,6,8-trioxa-5λ5,7λ5-diphospha-113λ5-1(9)-purina-13(5)-pyrimidina-11(5,3)-[1,3]thiazola-2(2,5)-oxolanatridecaphan-113-ylium
Identifiers
3D model (JSmol)
PubChem CID
  • InChI=1S/C22H29N9O10P2S/c1-11-15(44-10-30(11)6-13-5-25-12(2)29-19(13)23)3-4-38-42(34,35)41-43(36,37)39-7-14-17(32)18(33)22(40-14)31-9-28-16-20(24)26-8-27-21(16)31/h5,8-10,14,17-18,22,32-33H,3-4,6-7H2,1-2H3,(H5-,23,24,25,26,27,29,34,35,36,37)/p+1/t14-,17+,18+,22-/m1/s1
    Key: YLSJMTRFGUMRTH-HPXJRWHBSA-O
  • acid:CC1=C(SC=[N+]1CC2=CN=C(N=C2N)C)CCOP(=O)(O)OP(=O)(O)OC[C@@H]3[C@@H]([C@@H]([C@@H](O3)N4C=NC5=C(N=CN=C54)N)O)O
Properties
C22H28N9O10P2S
Molar mass 674.50 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Adenosine thiamine diphosphate (AThDP), or thiaminylated adenosine diphosphate (ADP) is a naturally occurring thiamine adenine nucleotide. It was chemically synthesized and exists in small amounts in vertebrate liver. Its biological significance remains unknown. [1] [2]

See also

Related Research Articles

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Nucleotides are organic molecules composed of a nitrogenous base, a pentose sugar and a phosphate. They serve as monomeric units of the nucleic acid polymers – deoxyribonucleic acid (DNA) and ribonucleic acid (RNA), both of which are essential biomolecules within all life-forms on Earth. Nucleotides are obtained in the diet and are also synthesized from common nutrients by the liver.

<span class="mw-page-title-main">Thiamine</span> Chemical compound

Thiamine, also known as thiamin and vitamin B1, is a vitamin, an essential micronutrient for humans and animals. It is found in food and commercially synthesized to be a dietary supplement or medication. Phosphorylated forms of thiamine are required for some metabolic reactions, including the breakdown of glucose and amino acids.

<span class="mw-page-title-main">Adenine</span> Chemical compound in DNA and RNA

Adenine is a purine nucleobase. It is one of the four nucleobases in the nucleic acids of DNA, the other three being guanine (G), cytosine (C), and thymine (T). Adenine derivatives have various roles in biochemistry including cellular respiration, in the form of both the energy-rich adenosine triphosphate (ATP) and the cofactors nicotinamide adenine dinucleotide (NAD), flavin adenine dinucleotide (FAD) and Coenzyme A. It also has functions in protein synthesis and as a chemical component of DNA and RNA. The shape of adenine is complementary to either thymine in DNA or uracil in RNA.

<span class="mw-page-title-main">Adenosine diphosphate</span> Chemical compound

Adenosine diphosphate (ADP), also known as adenosine pyrophosphate (APP), is an important organic compound in metabolism and is essential to the flow of energy in living cells. ADP consists of three important structural components: a sugar backbone attached to adenine and two phosphate groups bonded to the 5 carbon atom of ribose. The diphosphate group of ADP is attached to the 5’ carbon of the sugar backbone, while the adenine attaches to the 1’ carbon.

<span class="mw-page-title-main">Pyrophosphate</span> Class of chemical compounds

In chemistry, pyrophosphates are phosphorus oxyanions that contain two phosphorus atoms in a P–O–P linkage. A number of pyrophosphate salts exist, such as disodium pyrophosphate (Na2H2P2O7) and tetrasodium pyrophosphate (Na4P2O7), among others. Often pyrophosphates are called diphosphates. The parent pyrophosphates are derived from partial or complete neutralization of pyrophosphoric acid. The pyrophosphate bond is also sometimes referred to as a phosphoanhydride bond, a naming convention which emphasizes the loss of water that occurs when two phosphates form a new P–O–P bond, and which mirrors the nomenclature for anhydrides of carboxylic acids. Pyrophosphates are found in ATP and other nucleotide triphosphates, which are important in biochemistry. The term pyrophosphate is also the name of esters formed by the condensation of a phosphorylated biological compound with inorganic phosphate, as for dimethylallyl pyrophosphate. This bond is also referred to as a high-energy phosphate bond.

<span class="mw-page-title-main">Nicotinamide adenine dinucleotide</span> Chemical compound which is reduced and oxidized

Nicotinamide adenine dinucleotide (NAD) is a coenzyme central to metabolism. Found in all living cells, NAD is called a dinucleotide because it consists of two nucleotides joined through their phosphate groups. One nucleotide contains an adenine nucleobase and the other, nicotinamide. NAD exists in two forms: an oxidized and reduced form, abbreviated as NAD+ and NADH (H for hydrogen), respectively.

<span class="mw-page-title-main">Ribonucleotide</span> Nucleotide containing ribose as its pentose component

In biochemistry, a ribonucleotide is a nucleotide containing ribose as its pentose component. It is considered a molecular precursor of nucleic acids. Nucleotides are the basic building blocks of DNA and RNA. Ribonucleotides themselves are basic monomeric building blocks for RNA. Deoxyribonucleotides, formed by reducing ribonucleotides with the enzyme ribonucleotide reductase (RNR), are essential building blocks for DNA. There are several differences between DNA deoxyribonucleotides and RNA ribonucleotides. Successive nucleotides are linked together via phosphodiester bonds.

<span class="mw-page-title-main">Cofactor (biochemistry)</span> Non-protein chemical compound or metallic ion

A cofactor is a non-protein chemical compound or metallic ion that is required for an enzyme's role as a catalyst. Cofactors can be considered "helper molecules" that assist in biochemical transformations. The rates at which these happen are characterized in an area of study called enzyme kinetics. Cofactors typically differ from ligands in that they often derive their function by remaining bound.

A salvage pathway is a pathway in which a biological product is produced from intermediates in the degradative pathway of its own or a similar substance. The term often refers to nucleotide salvage in particular, in which nucleotides are synthesized from intermediates in their degradative pathway.

<span class="mw-page-title-main">Adenylate kinase</span> Class of enzymes

Adenylate kinase is a phosphotransferase enzyme that catalyzes the interconversion of the various adenosine phosphates. By constantly monitoring phosphate nucleotide levels inside the cell, ADK plays an important role in cellular energy homeostasis.

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<span class="mw-page-title-main">Nucleic acid metabolism</span> Process

Nucleic acid metabolism is a collective term that refers to the variety of chemical reactions by which nucleic acids are either synthesized or degraded. Nucleic acids are polymers made up of a variety of monomers called nucleotides. Nucleotide synthesis is an anabolic mechanism generally involving the chemical reaction of phosphate, pentose sugar, and a nitrogenous base. Degradation of nucleic acids is a catabolic reaction and the resulting parts of the nucleotides or nucleobases can be salvaged to recreate new nucleotides. Both synthesis and degradation reactions require multiple enzymes to facilitate the event. Defects or deficiencies in these enzymes can lead to a variety of diseases.

<span class="mw-page-title-main">Phosphodiesterase 2</span> Class of enzymes

The PDE2 enzyme is one of 21 different phosphodiesterases (PDE) found in mammals. These different PDEs can be subdivided to 11 families. The different PDEs of the same family are functionally related despite the fact that their amino acid sequences show considerable divergence. The PDEs have different substrate specificities. Some are cAMP selective hydrolases, others are cGMP selective hydrolases and the rest can hydrolyse both cAMP and cGMP.

<span class="mw-page-title-main">Thiamine triphosphate</span> Chemical compound

Thiamine triphosphate (ThTP) is a biomolecule found in most organisms including bacteria, fungi, plants and animals. Chemically, it is the triphosphate derivative of the vitamin thiamine.

Adenosine thiamine triphosphate (AThTP), or thiaminylated adenosine triphosphate, is a natural thiamine adenine nucleotide. It was discovered in Escherichia coli where it may account for up to 15 - 20% of total thiamine under carbon starvation. AThTP also exists in eukaryotic organisms such as yeast, roots of higher plants and animal tissues, albeit at a much lower concentration. It was found to exist in small amounts in the muscle, heart, brain, kidneys and liver of mice.

<span class="mw-page-title-main">Nucleoside-diphosphatase</span> Group of proteins having nucleoside-diphosphatase activity

In enzymology, a nucleoside-diphosphatase (EC 3.6.1.6) is an enzyme that catalyzes the chemical reaction

<span class="mw-page-title-main">Adenosine 3',5'-bisphosphate</span> Chemical compound

Adenosine 3',5'-bisphosphate is a form of an adenosine nucleotide with two phosphate groups attached to different carbons in the ribose ring. This is distinct from adenosine diphosphate, where the two phosphate groups are attached in a chain to the 5' carbon atom in the ring.

In enzymology, a FMN adenylyltransferase is an enzyme that catalyzes the chemical reaction

<span class="mw-page-title-main">Nicotinamide-nucleotide adenylyltransferase</span>

In enzymology, nicotinamide-nucleotide adenylyltransferase (NMNAT) (EC 2.7.7.1) are enzymes that catalyzes the chemical reaction

<span class="mw-page-title-main">Purinergic signalling</span> Signalling complex involving purine nucleosides and their receptors

Purinergic signalling is a form of extracellular signalling mediated by purine nucleotides and nucleosides such as adenosine and ATP. It involves the activation of purinergic receptors in the cell and/or in nearby cells, thereby regulating cellular functions.

References

  1. Bettendorff L (November 2021). "Update on Thiamine Triphosphorylated Derivatives and Metabolizing Enzymatic Complexes". Biomolecules. 11 (11). doi:10.3390/biom11111645. PMC   8615392 . PMID   34827643.
  2. Frédérich M.; Delvaux D.; Gigliobianco T.; Gangolf M.; Dive G.; Mazzucchelli G.; Elias B.; De Pauw E.; Angenot L.; Wins P.; Bettendorff L. (2009). "Thiaminylated adenine nucleotides — chemical synthesis, structural characterization and natural occurrence FEBS J.". The FEBS Journal. 276 (12): 3256–3268. doi:10.1111/j.1742-4658.2009.07040.x. PMID   19438713.