Phenylacetyl-CoA

Last updated
Phenylacetyl-CoA
Phenylacetyl-CoA.svg
Chemical structure of phenylacetyl-CoA
Names
IUPAC name
3′-O-Phosphonoadenosine 5′-[(3R)-3-hydroxy-2-methyl-4-{[3-oxo-3-({2-[(phenylacetyl)sulfanyl]ethyl}amino)propyl]amino}-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-2-methyl-4-{[3-oxo-3-({2-[(phenylacetyl)sulfanyl]ethyl}amino)propyl]amino}-4-oxobutyl] dihydrogen diphosphate
Identifiers
3D model (JSmol)
3DMet
ChEBI
ChEMBL
ChemSpider
KEGG
PubChem CID
  • InChI=1S/C29H42N7O17P3S/c1-29(2,24(40)27(41)32-9-8-19(37)31-10-11-57-20(38)12-17-6-4-3-5-7-17)14-50-56(47,48)53-55(45,46)49-13-18-23(52-54(42,43)44)22(39)28(51-18)36-16-35-21-25(30)33-15-34-26(21)36/h3-7,15-16,18,22-24,28,39-40H,8-14H2,1-2H3,(H,31,37)(H,32,41)(H,45,46)(H,47,48)(H2,30,33,34)(H2,42,43,44)/t18-,22-,23-,24+,28-/m1/s1
    Key: ZIGIFDRJFZYEEQ-CECATXLMSA-N
  • 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)CC4=CC=CC=C4)O
Properties
C29H42N7O17P3S
Molar mass 885.67 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Phenylacetyl-CoA (C29H42N7O17P3S) is a form of acetyl-CoA formed from the condensation of the thiol group from coenzyme A with the carboxyl group of phenylacetic acid. [1] [2]

Its molecular-weight is 885.7 g/mol. and IUPAC name is S-[2-[3-[[(2R)-4-[[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxy-2-hydroxy-3,3-dimethylbutanoyl]amino]propanoylamino]ethyl] 2-phenylethanethioate. It is formed via the actions of Phenylacetate—CoA ligase. [3]

Phenylacetyl-CoA is often produced via the reduction of ATP to AMP and the conversion of phenylacetate and CoA to diphosphate and Phenylacetyl-CoA.

ATP + phenylacetate + CoA → AMP + diphosphate + phenylacetyl-CoA

This reaction is catalyzed by phenylacetate-CoA ligase.

Phenylacetyl-CoA combines with water and quinone to produce phenylglyoxylyl-CoA and quinol via a phenylacetyl-CoA dehydrogenase reaction acting as an oxidoreductase.

Phenylacetyl-CoA inhibits choline acetyltransferase acting as a neurotoxin. It competes with acetyl-CoA. [4]

Related Research Articles

<span class="mw-page-title-main">Citric acid cycle</span> Chemical reactions to release energy in cells

The citric acid cycle (CAC)—also known as the Krebs cycle, Szent-Györgyi-Krebs cycle or the TCA cycle (tricarboxylic acid cycle)—is a series of chemical reactions to release stored energy through the oxidation of acetyl-CoA derived from carbohydrates, fats, and proteins. The Krebs cycle is used by organisms that respire (as opposed to organisms that ferment) to generate energy, either by anaerobic respiration or aerobic respiration. In addition, the cycle provides precursors of certain amino acids, as well as the reducing agent NADH, that are used in numerous other reactions. Its central importance to many biochemical pathways suggests that it was one of the earliest components of metabolism. Even though it is branded as a 'cycle', it is not necessary for metabolites to follow only one specific route; at least three alternative segments of the citric acid cycle have been recognized.

Holocarboxylase synthetase ), also known as protein—biotin ligase, is a family of enzymes. This enzyme is important for the effective use of biotin, a B vitamin found in foods such as liver, egg yolks, and milk. In many of the body's tissues, holocarboxylase synthetase activates other specific enzymes by attaching biotin to them. These carboxylases are involved in many critical cellular functions, including the production and breakdown of proteins, fats, and carbohydrates.

<span class="mw-page-title-main">Long-chain-fatty-acid—CoA ligase</span> Class of enzymes

The long chain fatty acyl-CoA ligase is an enzyme of the ligase family that activates the oxidation of complex fatty acids. Long chain fatty acyl-CoA synthetase catalyzes the formation of fatty acyl-CoA by a two-step process proceeding through an adenylated intermediate. The enzyme catalyzes the following reaction,

In enzymology, an aryl-aldehyde dehydrogenase (NADP+) (EC 1.2.1.30) is an enzyme that catalyzes the chemical reaction

In enzymology, a 3α,7α-dihydroxy-5β-cholestanate—CoA ligase is an enzyme that catalyzes the chemical reaction

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

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

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

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

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

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

In enzymology, a biotin—[acetyl-CoA-carboxylase] 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 [citrate (pro-3S)-lyase] ligase is an enzyme that catalyzes the chemical reaction

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

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

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

ATP citrate synthase (also ATP citrate lyase (ACLY)) is an enzyme that in animals represents an important step in fatty acid biosynthesis. By converting citrate to acetyl-CoA, the enzyme links carbohydrate metabolism, which yields citrate as an intermediate, with fatty acid biosynthesis, which consumes acetyl-CoA. In plants, ATP citrate lyase generates cytosolic acetyl-CoA precursors of thousands of specialized metabolites, including waxes, sterols, and polyketides.

Phenylacetyl-CoA 1,2-epoxidase (EC 1.14.13.149, ring 1,2-phenylacetyl-CoA epoxidase, phenylacetyl-CoA monooxygenase, PaaAC, PaaABC(D)E) is an enzyme with systematic name phenylacetyl-CoA:oxygen oxidoreductase (1,2-epoxidizing). This enzyme catalyses the following chemical reaction

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

References

  1. ↑ PubChem. "Phenylacetyl-CoA". pubchem.ncbi.nlm.nih.gov.
  2. ↑ García, Belén; Olivera, Elías R.; Miñambres, Baltasar; Carnicero, David; Muñiz, Carmen; Naharro, Germán; Luengo, José M. (October 2000). "Phenylacetyl-Coenzyme A Is the True Inducer of the Phenylacetic Acid Catabolism Pathway in Pseudomonas putida U". Applied and Environmental Microbiology. 66 (10): 4575–4578. Bibcode:2000ApEnM..66.4575G. doi:10.1128/aem.66.10.4575-4578.2000. PMC   92347 . PMID   11010921.
  3. ↑ Rhee, Sung-Keun; Fuchs, Georg (1999). "Phenylacetyl-CoA:acceptor oxidoreductase, a membrane-bound molybdenum–iron–sulfur enzyme involved in anaerobic metabolism of phenylalanine in the denitrifying bacterium Thauera aromatica". European Journal of Biochemistry. 262 (2): 507–515. doi: 10.1046/j.1432-1327.1999.00399.x . ISSN   1432-1033. PMID   10336636.
  4. ↑ "Human Metabolome Database: Showing metabocard for Phenylacetyl-CoA (HMDB0006503)". www.hmdb.ca. Retrieved 2019-11-06.
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