3-Hydroxybenzoyl-CoA: Difference between revisions
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| ImageAlt = Chemical structure of 3-Hydroxybenzoyl-CoA |
| ImageAlt = Chemical structure of 3-Hydroxybenzoyl-CoA |
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| ImageCaption = Chemical structure of 3-Hydroxybenzoyl-CoA |
| ImageCaption = Chemical structure of 3-Hydroxybenzoyl-CoA |
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| IUPACName = Adenosine 5′-[(3''R'')-3-hydroxy-4-{[3-({2-[(3-hydroxybenzoyl)sulfanyl]ethyl}amino)-3-oxopropyl]amino}-2-methyl-4-oxobutyl dihydrogen diphosphate] |
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| SystematicName = ''O''<sup>1</sup>-<nowiki/>{[(2''R'',3''S'',4''R'',5''R'')-5-(6-Amino-9''H''-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methyl} ''O''<sup>3</sup>-[(3''R'')-3-hydroxy-4-{[3-({2-[(3-hydroxybenzoyl)sulfanyl]ethyl}amino)-3-oxopropyl]amino}-2-methyl-4-oxobutyl] dihydrogen diphosphate |
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| OtherNames = {{bulletedlist|3-Hydroxybenzoyl-coenzyme A|''m''-Hydroxybenzoyl-CoA|''m''-Hydroxybenzoyl-coenzyme A}} |
| OtherNames = {{bulletedlist|3-Hydroxybenzoyl-coenzyme A|''m''-Hydroxybenzoyl-CoA|''m''-Hydroxybenzoyl-coenzyme A}} |
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| Section1 = {{Chembox Identifiers |
| Section1 = {{Chembox Identifiers |
Revision as of 01:01, 27 April 2023
Chemical structure of 3-Hydroxybenzoyl-CoA
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Names | |
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IUPAC name
Adenosine 5′-[(3R)-3-hydroxy-4-{[3-({2-[(3-hydroxybenzoyl)sulfanyl]ethyl}amino)-3-oxopropyl]amino}-2-methyl-4-oxobutyl dihydrogen diphosphate]
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Systematic IUPAC name
O1-{[(2R,3S,4R,5R)-5-(6-Amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methyl} O3-[(3R)-3-hydroxy-4-{[3-({2-[(3-hydroxybenzoyl)sulfanyl]ethyl}amino)-3-oxopropyl]amino}-2-methyl-4-oxobutyl] dihydrogen diphosphate | |
Other names
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Identifiers | |
3D model (JSmol)
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ChEBI | |
ChemSpider | |
KEGG | |
PubChem CID
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Properties | |
C28H40N7O18P3S | |
Molar mass | 887.64 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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3-Hydroxybenzoyl-CoA is a molecule formed by condensing the thiol group of coenzyme A (CoA) with the carboxylic acid group of 3-hydroxybenzoic acid. Stable in acidic conditions, it is a tetraprotic acid due to the pyrophosphate and phosphate groups included. It derives from a benzoyl-CoA and a 3-hydroxybenzoic acid. In organisms such as plants, this can be formed using the 3-hydroxybenzoate—CoA ligase enzyme. This uses ATP, 3-hydroxybenzoate, and CoA as substrates.[1]
It can be reduced to 3-hydroxycyclohexa-1,5-diene-1-carbonyl-CoA by reduced ferredoxin and adenosine triphosphate using the benzoyl-CoA reductase enzyme.[2] in this two hydrogen atoms are added to the benzene ring in a dearomatizing process.
References
- ^ "BRENDA - Information on EC 6.2.1.37 - 3-hydroxybenzoate-CoA ligase". www.brenda-enzymes.org.
- ^ "bcrA - Benzoyl-CoA reductase subunit A - Thauera aromatica - bcrA gene & protein". www.uniprot.org.