Coenzyme A
IUPAC name	3-hydroxy-4-(3-(2-mercaptoethylamino)-3-oxopropylamino)-2,2-dimethylpent-4-enyl diphosphate 5-(8-amino-3,4-dihydropyrimido[5,4-d]pyrimidin-4-yl)-2-(ethan-1-ylium-2-yl)-4-hydroxytetrahydrofuran-3-yl phosphate
Identifiers
CAS number	[85-61-0]
PubChem	317
MeSH	Coenzyme+A
Properties
Molecular formula	C21H36N7O16P3S
Molar mass	767.535
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Coenzyme A (CoA, CoASH, or HSCoA) is a coenzyme, notable for its role in the synthesis and oxidization of fatty acids, and the oxidation of pyruvate in the citric acid cycle. It is adapted from cysteamine, pantothenate and adenosine triphosphate. Image File history File links No higher resolution available. ... Image File history File links Size of this preview: 800 × 312 pixel Image in higher resolution (1100 × 429 pixel, file size: 140 KB, MIME type: image/png) File links The following pages on the English Wikipedia link to this file (pages on other projects are not listed): Coenzyme A ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... PubChem is a database of chemical molecules. ... Medical Subject Headings (MeSH) is a huge controlled vocabulary (or metadata system) for the purpose of indexing journal articles and books in the life sciences. ... This article or section does not cite any references or sources. ... Molar mass is the mass of one mole of a chemical element or chemical compound. ... In chemistry, the standard state of a material is its state at 1 bar (100 kilopascals) and 25 degrees Celsius (298. ... Coenzyme A Coenzymes are small organic non-protein molecules that carry chemical groups between enzymes. ... Fatty acids are an important source of energy for many organisms. ... Fatty acids are an important source of energy for many organisms. ... In chemistry, especially biochemistry, a fatty acid is a carboxylic acid often with a long unbranched aliphatic tail (chain), which is either saturated or unsaturated. ... Pyruvic acid (CH3COCO2H) is an alpha-keto acid which plays an important role in biochemical processes. ... Overview of the citric acid cycle The citric acid cycle (also known as the tricarboxylic acid cycle, the TCA cycle, or the Krebs cycle, after Hans Adolf Krebs who identified the cycle) is a series of chemical reactions of central importance in all living cells that use oxygen as part... Cysteamine is an medication (trade name Cystagon) used in the treatment of disorders of cystine excretion. ... Pantothenic acid, also called vitamin B5, is a water-soluble vitamin required to sustain life. ... Adenosine 5-triphosphate (ATP) is a multifunctional nucleotide that is most important as a molecular currency of intracellular energy transfer. ...

Biosynthesis

Coenzyme A is synthesized in a five-step process from pantothenate:

1. Pantothenate is phosphorylated to 4'-phosphopantothenate by the enzyme pantothenate kinase
2. A cysteine is added to 4'-phosphopantothenate by the enzyme phosphopantothenoylcysteine synthetase to form 4'-phospho-N-pantothenoylcysteine (PPC)
3. PPC is decarboxylated to 4'-phosphopantetheine by phosphopantothenoylcysteine decarboxylase
4. 4'-phosphopantetheine is adenylylated to form dephospho-CoA by the enzyme phosphopantetheine adenylyl transerase
5. Finally, dephospho-CoA is phosphorylated using ATP to coenzyme A by the enzyme dephosphocoenzyme A kinase.

Pantothenic acid, also called vitamin B5 (a B vitamin), is a water-soluble vitamin required to sustain life (essential nutrient). ... Pantothenate kinase is an enzyme involved in the synthesis of Coenzyme A. PANK1, PANK2, PANK3, PANK4. ... Pantetheine is the mercaptoethyl conjugated amide analogue of pantothenic acid (Vitamin B5). ... Pantetheine is the mercaptoethyl conjugated amide analogue of pantothenic acid (Vitamin B5). ...

Function

Since coenzyme A is chemically a thiol, it can react with carboxylic acids to form thioesters, thus functioning as an acyl group carrier. A molecule of coenzyme A carrying an acetyl group is also referred to as acetyl-CoA. When it is not attached to an acyl group it is usually referred to as 'CoASH' or 'HSCoA'. Sulphydryl // In organic chemistry, a thiol is a compound that contains the functional group composed of a sulfur atom and a hydrogen atom (-SH). ... Structure of a carboxylic acid The 3D structure of the carboxyl group A space-filling model of the carboxyl group Carboxylic acids are organic acids characterized by the presence of a carboxyl group, which has the formula -C(=O)OH, usually written -COOH or -CO2H. [1] Carboxylic acids are Bronsted... Thioesters are compounds resulting from the bonding of sulfur with an acyl group (an alkyl group attached to a carbon-oxygen double bond), with the general formula R-S-CO-R. Some biochemists believe that the thioester bond was critical for the origin of life. ... In chemistry, the terms acyl or acyl group refer to a functional group obtained from an acid by removal of a hydroxyl group. ... Acetyl is the radical of acetic acid. ... Categories: Biochemistry stubs | Thiols ...

List of coenzyme A activated acyl groups

• Acetyl-CoA
• Propionyl-CoA
• Acetoacetyl-CoA
• Coumaroyl-CoA (used in flavonoid and stilbenoid biosynthesis)
• Acyl derived from dicarboxylic acids
  • Malonyl-CoA
  • Succinyl-CoA
  • Hydroxymethylglutaryl-CoA (used in isoprenoid biosynthesis)
  • Pimelyl-CoA (used in biotin biosynthesis)

Categories: Biochemistry stubs | Thiols ... Propionyl-CoA is a coenzyme A derivative of propionic acid. ... The mevalonate pathway or HMG-CoA reductase pathway or mevalonate-dependent (MAD) route, is an important cellular metabolic pathway present in all higher eukaryotes and many bacteria. ... Coumaric acids are organic compounds that are hydroxy derivatives of cinnamic acid. ... Molecular structure of flavone The term flavonoid refers to a class of plant secondary metabolites based around a phenylbenzopyrone structure. ... Stilbenoids are secondary products of heartwood formation in trees that can act as phytoalexins. ... Dicarboxylic acids are organic compounds that are substituted with two carboxylic acid functional groups. ... -1... Categories: Biochemistry stubs ... The mevalonate pathway or HMG-CoA reductase pathway or mevalonate-dependent (MAD) route, is an important cellular metabolic pathway present in all higher eukaryotes and many bacteria. ... The terpenoids, sometimes referred to as isoprenoids, are a class of naturally occurring chemicals similar to terpenes, derived from five-carbon isoprene units assembled and modified in thousands of ways. ... Pimelic acid (IUPAC systematic name: heptanedioic acid) is a dicarboxylic acid, with formula C5H10(COOH)2. ... Vitamin H redirects here. ...

Additional images

Coenzyme A Image File history File links This is a lossless scalable vector image. ...

References

• Karl Miller (1998). Beta Oxidation of Fatty Acids. Retrieved May 18, 2005.
• Charles Ophard (2003). Acetyl-CoA Crossroads. Retrieved May 18, 2005.
• Lehninger: Principles of Biochemistry, 4th edition, David L. Nelson, Michael M. Cox

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Coenzyme A

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External links

• Links to external chemical sources