Benzoyl-CoA

Last updated
Benzoyl-Coenzyme A
Benzoyl-CoA.svg
Names
Other names
benzoyl-S-CoA
S-Benzoate coenzyme A
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
PubChem CID
UNII
  • InChI=1S/C28H40N7O17P3S/c1-28(2,22(38)25(39)31-9-8-18(36)30-10-11-56-27(40)16-6-4-3-5-7-16)13-49-55(46,47)52-54(44,45)48-12-17-21(51-53(41,42)43)20(37)26(50-17)35-15-34-19-23(29)32-14-33-24(19)35/h3-7,14-15,17,20-22,26,37-38H,8-13H2,1-2H3,(H,30,36)(H,31,39)(H,44,45)(H,46,47)(H2,29,32,33)(H2,41,42,43)/t17-,20-,21-,22+,26-/m1/s1 X mark.svgN
    Key: VEVJTUNLALKRNO-TYHXJLICSA-N X mark.svgN
  • InChI=1/C28H40N7O17P3S/c1-28(2,22(38)25(39)31-9-8-18(36)30-10-11-56-27(40)16-6-4-3-5-7-16)13-49-55(46,47)52-54(44,45)48-12-17-21(51-53(41,42)43)20(37)26(50-17)35-15-34-19-23(29)32-14-33-24(19)35/h3-7,14-15,17,20-22,26,37-38H,8-13H2,1-2H3,(H,30,36)(H,31,39)(H,44,45)(H,46,47)(H2,29,32,33)(H2,41,42,43)/t17-,20-,21-,22+,26-/m1/s1
    Key: VEVJTUNLALKRNO-TYHXJLICBE
  • CC(C)(COP(=O)(O)OP(=O)(O)OC[C@@H]1[C@H]([C@H]([C@@H](O1)N2C=NC3=C(N=CN=C32)N)O)OP(=O)(O)O)[C@H](C(=O)NCCC(=O)NCCSC(=O)C4=CC=CC=C4)O
Properties
C28H36N7O17P3S−4
Molar mass 867.60 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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Benzoyl-CoA is the thioester derived from benzoic acid and coenzyme A. The term benzoyl-CoA also include diverse conjugates of coenzyme A and aromatic carboxylic acids. Benzoate, vanillin, anthranilic acid, 4-ethylphenol, p-cresol, phenol, aniline, terephthalic acid, [3-hydroxybenzoic acid, and phenylalanine are all metabolized to benzoyl-CoA. Additionally, cinnamic acid, p-coumaric acid, ferulic acid, toluene, caffeic acid, benzyl alcohol, and mandelic acid are suspected to be processed similarly. [1]

Contents

As substrate for reductases

Benzoyl CoA is processed anaerobically to the cyclohexadiene derivative. Benzoyl CoA processing.svg
Benzoyl CoA is processed anaerobically to the cyclohexadiene derivative.

Benzoyl-CoA is a substrate for diverse reductases: [1] 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). Benzoyl-CoA reductase converts benzoyl-CoA to cyclohex-1,5-diene-1-carbonyl-CoA, which is susceptible to hydrolysis, eventually giving acetyl coenzyme A. In this way, many aromatic compounds are biodegraded.

As a benzoyl donor

Benzoyl-CoA is a benzoyl transfer agent for the biosynthesis of hippuric acid. Benzoyl-CoA is a substrate in the formation of xanthonoids in Hypericum androsaemum by benzophenone synthase, condensing a molecule of benzoyl-CoA with three malonyl-CoA, yielding to 2,4,6-trihydroxybenzophenone. This intermediate is subsequently converted by a benzophenone 3′-hydroxylase, a cytochrome P450 monooxygenase, leading to the formation of 2,3′,4,6-tetrahydroxybenzophenone. [2]

Benzoyl-CoA is a substrate of benzoyl-CoA reductase. This enzyme is responsible in part for the reductive dearomatization of aryl compounds mediated by bacteria under anaerobic conditions. [3]

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.

Cyclohexa-1,3-diene (also known as Benzane) is an organic compound with the formula (C2H4)(CH)4. It is a colorless, flammable liquid. Its refractive index is 1.475 (20 °C, D). It is one of two isomers of cyclohexadiene, the other being 1,4-cyclohexadiene.

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

Phenylacetone, also known as phenyl-2-propanone, is an organic compound with the chemical formula C6H5CH2COCH3. It is a colorless oil that is soluble in organic solvents. It is a mono-substituted benzene derivative, consisting of an acetone attached to a phenyl group. As such, its systematic IUPAC name is 1-phenyl-2-propanone.

<span class="mw-page-title-main">4-Hydroxybenzoic acid</span> Chemical compound

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.

<span class="mw-page-title-main">Chalcone synthase</span>

Chalcone synthase or naringenin-chalcone synthase (CHS) is an enzyme ubiquitous to higher plants and belongs to a family of polyketide synthase enzymes (PKS) known as type III PKS. Type III PKSs are associated with the production of chalcones, a class of organic compounds found mainly in plants as natural defense mechanisms and as synthetic intermediates. CHS was the first type III PKS to be discovered. It is the first committed enzyme in flavonoid biosynthesis. The enzyme catalyzes the conversion of 4-coumaroyl-CoA and malonyl-CoA to naringenin chalcone.

In enzymology, a 4-hydroxybenzoyl-CoA reductase (EC 1.3.7.9) is an enzyme found in some bacteria and archaea that catalyzes the chemical reaction

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

<span class="mw-page-title-main">Coenzyme-B sulfoethylthiotransferase</span> Class of enzymes

In enzymology, coenzyme-B sulfoethylthiotransferase, also known as methyl-coenzyme M reductase (MCR) or most systematically as 2-(methylthio)ethanesulfonate:N-(7-thioheptanoyl)-3-O-phosphothreonine S-(2-sulfoethyl)thiotransferase is an enzyme that catalyzes the final step in the formation of methane. It does so by combining the hydrogen donor coenzyme B and the methyl donor coenzyme M. Via this enzyme, most of the natural gas on earth was produced. Ruminants produce methane because their rumens contain methanogenic prokaryotes (Archaea) that encode and express the set of genes of this enzymatic complex.

<span class="mw-page-title-main">Benzylsuccinate synthase</span>

The enzyme benzylsuccinate synthase catalyzes the chemical reaction

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

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

The enzyme chorismate synthase catalyzes the chemical reaction

<span class="mw-page-title-main">Hydroxymethylglutaryl-CoA synthase</span> Class of enzymes

In molecular biology, hydroxymethylglutaryl-CoA synthase or HMG-CoA synthase EC 2.3.3.10 is an enzyme which catalyzes the reaction in which acetyl-CoA condenses with acetoacetyl-CoA to form 3-hydroxy-3-methylglutaryl-CoA (HMG-CoA). This reaction comprises the second step in the mevalonate-dependent isoprenoid biosynthesis pathway. HMG-CoA is an intermediate in both cholesterol synthesis and ketogenesis. This reaction is overactivated in patients with diabetes mellitus type 1 if left untreated, due to prolonged insulin deficiency and the exhaustion of substrates for gluconeogenesis and the TCA cycle, notably oxaloacetate. This results in shunting of excess acetyl-CoA into the ketone synthesis pathway via HMG-CoA, leading to the development of diabetic ketoacidosis.

Coumaroyl-coenzyme A is the thioester of coenzyme-A and coumaric acid. Coumaroyl-coenzyme A is a central intermediate in the biosynthesis of myriad natural products found in plants. These products include lignols, flavonoids, isoflavonoids, coumarins, aurones, stilbenes, catechin, and other phenylpropanoids.

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

A xanthonoid is a chemical natural phenolic compound formed from the xanthone backbone. Many members of the Clusiaceae contain xanthonoids.

<span class="mw-page-title-main">Cobalamin biosynthesis</span>

Cobalamin biosynthesis is the process by which bacteria and archea make cobalamin, vitamin B12. Many steps are involved in converting aminolevulinic acid via uroporphyrinogen III and adenosylcobyric acid to the final forms in which it is used by enzymes in both the producing organisms and other species, including humans who acquire it through their diet.

Benzyl alcohol O-benzoyltransferase is an enzyme with systematic name benzoyl-CoA:benzyl alcohol O-benzoyltransferase. This enzyme catalyses the following chemical reaction

<i>p</i>-Hydroxynorephedrine Chemical compound

p-Hydroxynorephedrine (PHN), or 4-hydroxynorephedrine, is the para-hydroxy analog of norephedrine and an active sympathomimetic metabolite of amphetamine in humans. When it occurs as a metabolite of amphetamine, it is produced from both p-hydroxyamphetamine and norephedrine.

<span class="mw-page-title-main">4-Hydroxyphenylacetone</span> Chemical compound

4-Hydroxyphenylacetone is the para-hydroxy analog of phenylacetone, an inactive metabolite of amphetamine in humans. When it occurs as a metabolite of amphetamine, it is produced directly from the inactive metabolite phenylacetone.

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

Chlorophyllide a and Chlorophyllide b are the biosynthetic precursors of chlorophyll a and chlorophyll b respectively. Their propionic acid groups are converted to phytyl esters by the enzyme chlorophyll synthase in the final step of the pathway. Thus the main interest in these chemical compounds has been in the study of chlorophyll biosynthesis in plants, algae and cyanobacteria. Chlorophyllide a is also an intermediate in the biosynthesis of bacteriochlorophylls.

References

  1. 1 2 Porter, A. W.; Young, L. Y. (2014). "Benzoyl-CoA, a Universal Biomarker for Anaerobic Degradation of Aromatic Compounds". Advances in Applied Microbiology. 88: 167–203. doi:10.1016/B978-0-12-800260-5.00005-X. ISBN   978-0-12-800260-5. PMID   24767428.
  2. ↑ Alternative pathways of xanthone biosynthesis in cell cultures of Hypericum androsaemum L. Werner Schmidt and Ludger Beerhues, FEBS Letters, Volume 420, Issues 2-3, 29 December 1997, Pages 143-146, doi : 10.1016/S0014-5793(97)01507-X
  3. ↑ Matthias Boll , Georg Fuchs , Johann Heider "Anaerobic oxidation of aromatic compounds and hydrocarbons" Current Opinion in Chemical Biology 2002 Volume 6, pp. 604–611. doi : 10.1016/S1367-5931(02)00375-7
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