3-Hydroxybenzoyl-CoA

Last updated
3-Hydroxybenzoyl-CoA
3-Hydroxybenzoyl-CoA.svg
Chemical structure of 3-Hydroxybenzoyl-CoA
Names
IUPAC name
3′-O-Phosphonoadenosine 5′-[(3R)-3-hydroxy-4-{[3-({2-[(3-hydroxybenzoyl)sulfanyl]ethyl}amino)-3-oxopropyl]amino}-2-methyl-4-oxobutyl dihydrogen diphosphate]
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
  • 3-Hydroxybenzoyl-coenzyme A
  • m-Hydroxybenzoyl-CoA
  • m-Hydroxybenzoyl-coenzyme A
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
PubChem CID
  • InChI=1S/C28H40N7O18P3S/c1-28(2,22(39)25(40)31-7-6-18(37)30-8-9-57-27(41)15-4-3-5-16(36)10-15)12-50-56(47,48)53-55(45,46)49-11-17-21(52-54(42,43)44)20(38)26(51-17)35-14-34-19-23(29)32-13-33-24(19)35/h3-5,10,13-14,17,20-22,26,36,38-39H,6-9,11-12H2,1-2H3,(H,30,37)(H,31,40)(H,45,46)(H,47,48)(H2,29,32,33)(H2,42,43,44)/t17-,20-,21-,22+,26-/m1/s1
    Key: JTBCMZVWWNFUFR-TYHXJLICSA-N
  • CC(C)(COP(=O)(O)OP(=O)(O)OCC1C(C(C(O1)N2C=NC3=C2N=CN=C3N)O)OP(=O (O)O)C(C(=O)NCCC(=O)NCCSC(=O)C4=CC(=CC=C4)O)O
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).

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.

Related Research Articles

<span class="mw-page-title-main">Benzoic acid</span> Organic compound (C6H5COOH)

Benzoic acid is a white solid organic compound with the formula C6H5COOH, whose structure consists of a benzene ring with a carboxyl substituent. The benzoyl group is often abbreviated "Bz", thus benzoic acid is also denoted as BzOH, since the benzoyl group has the formula –C6H5CO. It is the simplest aromatic carboxylic acid. The name is derived from gum benzoin, which was for a long time its only source.

<span class="mw-page-title-main">HMG-CoA reductase</span> Mammalian protein found in Homo sapiens

HMG-CoA reductase is the rate-controlling enzyme of the mevalonate pathway, the metabolic pathway that produces cholesterol and other isoprenoids. HMGCR catalyzes the conversion of HMG-CoA to mevalonic acid, a necessary step in the biosynthesis of cholesterol. Normally in mammalian cells this enzyme is competitively suppressed so that its effect is controlled. This enzyme is the target of the widely available cholesterol-lowering drugs known collectively as the statins, which help treat dyslipidemia.

Drug metabolism is the metabolic breakdown of drugs by living organisms, usually through specialized enzymatic systems. More generally, xenobiotic metabolism is the set of metabolic pathways that modify the chemical structure of xenobiotics, which are compounds foreign to an organism's normal biochemistry, such as any drug or poison. These pathways are a form of biotransformation present in all major groups of organisms and are considered to be of ancient origin. These reactions often act to detoxify poisonous compounds. The study of drug metabolism is called pharmacokinetics.

<span class="mw-page-title-main">Flavin adenine dinucleotide</span> Redox-active coenzyme

In biochemistry, flavin adenine dinucleotide (FAD) is a redox-active coenzyme associated with various proteins, which is involved with several enzymatic reactions in metabolism. A flavoprotein is a protein that contains a flavin group, which may be in the form of FAD or flavin mononucleotide (FMN). Many flavoproteins are known: components of the succinate dehydrogenase complex, α-ketoglutarate dehydrogenase, and a component of the pyruvate dehydrogenase complex.

4-Hydroxybenzoic acid, also known as p-hydroxybenzoic acid (PHBA), is a monohydroxybenzoic acid, a phenolic derivative of benzoic acid. It is a white crystalline solid that is slightly soluble in water and chloroform but more soluble in polar organic solvents such as alcohols and acetone. 4-Hydroxybenzoic acid is primarily known as the basis for the preparation of its esters, known as parabens, which are used as preservatives in cosmetics and some ophthalmic solutions. It is isomeric with 2-hydroxybenzoic acid, known as salicylic acid, a precursor to aspirin, and with 3-hydroxybenzoic acid.

In enzymology, a 4-hydroxybenzoate polyprenyltransferase is an enzyme that catalyzes the chemical reaction

In enzymology, a benzoyl-CoA reductase (EC 1.3.7.8) is an enzyme that catalyzes the chemical reaction

The enzyme 4-hydroxybenzoate decarboxylase (EC 4.1.1.61) catalyzes the chemical reaction

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

The enzyme chorismate lyase catalyzes the first step in ubiquinone biosynthesis, the removal of pyruvate from chorismate, to yield 4-hydroxybenzoate in Escherichia coli and other Gram-negative bacteria. It belongs to the family of lyases, specifically the oxo-acid-lyases, which cleave carbon-carbon bonds. The systematic name of this enzyme class is chorismate pyruvate-lyase (4-hydroxybenzoate-forming). Other names in common use include CL, CPL, and UbiC.

In enzymology, a 4-hydroxybenzoate—CoA ligase is an enzyme that catalyzes the chemical reaction

In enzymology, a benzoate—CoA ligase is an enzyme that catalyzes the chemical reaction

Butyrate—CoA ligase, also known as xenobiotic/medium-chain fatty acid-ligase (XM-ligase), is an enzyme that catalyzes the chemical reaction:

In enzymology, a long-chain-fatty-acid—luciferin-component ligase is an enzyme that catalyzes the chemical reaction

In enzymology, a glycine N-acyltransferase (GLYAT), also known as acyl-CoA:glycine N-acyltransferase (ACGNAT), is an enzyme that catalyzes the chemical reaction

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

Benzoyl-CoA is a molecule implied in the activity of the different enzymes 4-hydroxybenzoyl-CoA reductase, benzoyl-CoA reductase, benzoyl-CoA 3-monooxygenase, benzoate-CoA ligase, 2alpha-hydroxytaxane 2-O-benzoyltransferase, anthranilate N-benzoyltransferase, biphenyl synthase, glycine N-benzoyltransferase, ornithine N-benzoyltransferase and phenylglyoxylate dehydrogenase (acylating).

4-hydroxybenzoate geranyltransferase is an enzyme with systematic name geranyl-diphosphate:4-hydroxybenzoate 3-geranyltransferase. This enzyme catalyses the following chemical reaction

3-Hydroxybenzoate—CoA ligase is an enzyme with systematic name 3-hydroxybenzoate:CoA ligase (AMP-forming). This enzyme catalyses the following chemical reaction

4-Hydroxybenzoic acid 4-<i>O</i>-glucoside Chemical compound

4-Hydroxybenzoic acid 4-O-glucoside is a glucoside of p-hydroxybenzoic acid. It can be found in mycorrhizal and non-mycorrhizal roots of Norway spruces.

References

  1. ↑ "BRENDA - Information on EC 6.2.1.37 - 3-hydroxybenzoate-CoA ligase". www.brenda-enzymes.org.
  2. ↑ "bcrA - Benzoyl-CoA reductase subunit A - Thauera aromatica - bcrA gene & protein". www.uniprot.org.
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