acetyl coenzyme A

WordNet

1. the 1st letter of the Roman alphabet (同)a
2. the blood group whose red cells carry the A antigen (同)type_A, group A
3. the organic group of acetic acid (CH3CO-) (同)acetyl_group, acetyl radical, ethanoyl group, ethanoyl radical
4. a small molecule (not a protein but sometimes a vitamin) essential for the activity of some enzymes

PrepTutorEJDIC

1. answer / ampere
2. arsenicの化学記号

Wikipedia preview

出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/08/21 20:18:48」(JST)

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Acetyl-CoA

Names
IUPAC name 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] ethanethioate
Identifiers
CAS Number	72-89-9 Y
ChEBI	CHEBI:15351 Y
ChemSpider	392413 Y
IUPHAR/BPS	3038
Jmol 3D model	Interactive image Interactive image
MeSH	Acetyl+Coenzyme+A
PubChem	444493
InChI InChI=1S/C23H38N7O17P3S/c1-12(31)51-7-6-25-14(32)4-5-26-21(35)18(34)23(2,3)9-44-50(41,42)47-49(39,40)43-8-13-17(46-48(36,37)38)16(33)22(45-13)30-11-29-15-19(24)27-10-28-20(15)30/h10-11,13,16-18,22,33-34H,4-9H2,1-3H3,(H,25,32)(H,26,35)(H,39,40)(H,41,42)(H2,24,27,28)(H2,36,37,38)/t13-,16-,17-,18+,22-/m1/s1 Y Key: ZSLZBFCDCINBPY-ZSJPKINUSA-N Y InChI=1/C23H38N7O17P3S/c1-12(31)51-7-6-25-14(32)4-5-26-21(35)18(34)23(2,3)9-44-50(41,42)47-49(39,40)43-8-13-17(46-48(36,37)38)16(33)22(45-13)30-11-29-15-19(24)27-10-28-20(15)30/h10-11,13,16-18,22,33-34H,4-9H2,1-3H3,(H,25,32)(H,26,35)(H,39,40)(H,41,42)(H2,24,27,28)(H2,36,37,38)/t13-,16-,17-,18+,22-/m1/s1 Key: ZSLZBFCDCINBPY-ZSJPKINUBJ
SMILES O=C(SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(=O)(O)OP(=O)(O)OC[C@H]3O[C@@H](n2cnc1c(ncnc12)N)[C@H](O)[C@@H]3OP(=O)(O)O)C CC(=O)SCCNC(=O)CCNC(=O)[C@@H](C(C)(C)COP(=O)(O)OP(=O)(O)OC[C@@H]1[C@H]([C@H]([C@@H](O1)n2cnc3c2ncnc3N)O)OP(=O)(O)O)O
Properties
Chemical formula	C23H38N7O17P3S
Molar mass	809.57 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)
Infobox references

Acetyl coenzyme A or acetyl-CoA is an important molecule in metabolism, used in many biochemical reactions. Its main function is to convey the carbon atoms within the acetyl group to the citric acid cycle (Krebs cycle) to be oxidized for energy production. The structure of coenzyme A (CoASH or CoA) consists of a β-mercaptoethylamine group linked to the vitamin pantothenic acid through an amide linkage. The acetyl group (indicated in blue in the structural diagram on the right) of acetyl-CoA is linked by a "high energy" thioester bond to the sulfhydryl substituent of the β-mercaptoethylamine group. It is this thioester bond that makes acetyl-CoA one of the "high energy" compounds. Hydrolysis of the thioester bond is exergonic (-31.5 kJ). Acetyl-CoA is produced during breakdown of carbohydrates through glycolysis, as well as by the beta-oxidation of fatty acids. It then enters the citric acid cycle, where the acetyl group is further oxidized to carbon dioxide and water, with the energy thus released captured in the form of 11 ATP and 1 GTP molecules per acetyl group that enters the cycle.

Acetyl-CoA is also an important component in the biogenic synthesis of the neurotransmitter acetylcholine. Choline, in combination with acetyl-CoA, is catalyzed by the enzyme choline acetyltransferase to produce acetylcholine and a Coenzyme A byproduct.

Konrad Bloch and Feodor Lynen were awarded the 1964 Nobel Prize in Physiology and Medicine for their discoveries linking acetyl-CoA and fatty acid metabolism. Fritz Lipmann won the Nobel Prize in 1953 for his discovery of the cofactor Coenzyme A.

Functions

Pyruvate dehydrogenase and pyruvate formate lyase reactions

The oxidative conversion of pyruvate into acetyl-CoA is referred to as the pyruvate dehydrogenase reaction. It is catalyzed by the pyruvate dehydrogenase complex. Other conversions between pyruvate and acetyl-CoA are possible. For example, pyruvate formate lyase disproportionates pyruvate into acetyl-CoA and formic acid.

Direct synthesis

The two components of acetyl-CoA—the acetyl, supplied via acetate, and Coenzyme-A groups—can be linked directly, catalyzed by the enzyme acetyl—CoA synthetase. This process is involved in metabolism of carbon sugars. As a starting point for the citric acid cycle, the acetyl—Co-A synthetase route is less common than the pyruvate dehydrogenase route.

Fatty acid metabolism

Acetyl-CoA is produced by the breakdown of both carbohydrates (by glycolysis) and fats (by beta-oxidation). It then enters the citric acid cycle in the mitochondrion by combining with oxaloacetate to form citrate. This conversion results in the complete conversion of the acetyl group of acetyl-CoA to CO₂ and water. The energy released in this process is captured in the form of 12 high energy pyrophosphate bonds (1 GTP and 11 ATP molecules) per acetyl group (or acetic acid molecule) oxidized. Conversion to CO₂ is the fate of acetyl-CoA derived from glycolysis or β-oxidation of fatty acids, except under certain circumstances in the liver. In the liver oxaloacetate is wholly or partially diverted into the gluconeogenic pathway during fasting, starvation, a low carbohydrate diet, prolonged strenuous exercise, and in uncontrolled type 1 diabetes mellitus. Under these circumstances oxaloacetate is reduced to malate, which is then removed from the mitochondrion to be converted into glucose in the cytoplasm of the liver cells, from where it is released into the blood. In the liver, therefore, oxaloacetate is unavailable for condensation with the acetyl-CoA produced by the β-oxidation of fatty acids when significant gluconeogenesis has been stimulated (and glycolysis has been inhibited) by low (or absent) insulin and high glucagon concentrations in the blood. Under these circumstances two acetyl-CoA molecules condense to form acetoacetyl-CoA, which then gives rise to the formation of acetoacetate and beta-hydroxybutyrate. Acetoacetate, beta-hydroxybutyrate, and their spontaneous breakdown product, acetone, are frequently, but confusingly, known as ketone bodies (as they are not "bodies" at all, but water soluble chemical substances). The ketone bodies are released by the liver into the blood. All cells with mitochondria can take ketone bodies up from the blood and reconvert them into acetyl-CoA, which can then be used as fuel in their citric acid cycles, as no other tissue can divert its oxaloacetate into the gluconeogenic pathway in the way that the liver does. Unlike free fatty acids, ketone bodies can cross the blood-brain barrier and are therefore available as fuel for the cells of the central nervous system, acting as a substitute for glucose, on which these cells normally survive. The occurrence of high levels of ketone bodies in the blood during starvation, a low carbohydrate diet, prolonged heavy exercise, and uncontrolled type-1 diabetes mellitus is known as ketosis, and in its extreme form in out-of-control type-1 diabetes mellitus, as ketoacidosis.

On the other hand, when the insulin concentration in the blood is high, and that of glucagon is low (i.e. after meals), the acetyl-CoA produced by glycolysis condenses as normal with oxaloacetate to form citrate in the mitochondrion. However, instead of continuing through the citric acid cycle to be converted to carbon dioxide and water, the citrate is removed from the mitochondrion into the cytoplasm. There it is cleaved by ATP citrate lyase into acetyl-CoA and oxaloacetate. The oxaloacetate is returned to mitochondrion as malate (and then converted back into oxaloacetate to transfer more acetyl-CoA out of the mitochondrion). This cytosolic acetyl-CoA can then be used to synthesize fatty acids through carboxylation by acetyl CoA carboxylase into malonyl CoA, the first committed step in the synthesis of fatty acids. This conversion occurs primarily in the liver, adipose tissue and lactating mammary glands, where the fatty acids are combined with glycerol to form triglycerides, the major fuel reservoir of most animals. Fatty acids are also components of the phospholipids that make up the bulk of the lipid bilayers of all the cellular membranes.

In plants, de novo fatty acid synthesis occurs in the plastids. Many seeds accumulate large reservoirs of seed oils to support germination and early growth of the seedling before it is a net photosynthetic organism.

The cytosolic acetyl-CoA can also condense with acetoacetyl-CoA to form 3-hydroxy-3-methylglutaryl-CoA (HMG-CoA) which is the rate limiting step controlling the synthesis of cholesterol. Cholesterol can be used as is, as a structural component of cellular membranes, or it can be used to synthesize the steroid hormones, bile salts, and vitamin D.

Other reactions

• Acetyl-CoA is also the source of the acetyl group incorporated onto certain lysine residues of histone and nonhistone proteins in the posttranslational modification acetylation, a reaction catalyzed by acetyltransferases.
• In plants and animals, cytosolic acetyl-CoA is synthesized by ATP citrate lyase. When glucose is abundant in the blood of animals, it is converted via glycolysis in the cytosol to pyruvate, and then to acetyl-CoA in the mitochondrion. The excess of acetyl-CoA results in production of excess citrate, which is exported into the cytosol to give rise to cytosolic acetyl-CoA.
• Acetyl-CoA can be carboxylated in the cytosol by acetyl-CoA carboxylase, giving rise to malonyl-CoA, a substrate required for synthesis of flavonoids and related polyketides, for elongation of fatty acids to produce waxes, cuticle, and seed oils in members of the Brassica family, and for malonation of proteins and other phytochemicals.
• In plants, these include sesquiterpenes, brassinosteroids (hormones), and membrane sterols.

Interactive pathway map

Click on genes, proteins and metabolites below to visit Gene Wiki pages and related Wikipedia articles. The pathway can be downloaded and edited at WikiPathways.

[[File: [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] |{{{bSize}}}px|alt=TCA Cycle edit]] File:TCACycle WP78.png TCA Cycle edit

[[File: [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] |px|alt=Statin Pathway edit]] File:StatinPathway_WP430.png Statin Pathway edit

See also

• Malonyl-CoA decarboxylase

References

External links

• Acetyl Coenzyme A at the US National Library of Medicine Medical Subject Headings (MeSH)

UpToDate Contents

全文を閲覧するには購読必要です。 To read the full text you will need to subscribe.

• 1. 筋肉におけるエネルギー代謝 energy metabolism in muscle
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• 5. インスリン作用 insulin action

English Journal

• Label-free fluorescent enzymatic assay of citrate synthase by CoA-Au(I) co-ordination polymer and its application in a multi-enzyme logic gate cascade.

• Li Y1, Wang H1, Dai F1, Li P1, Jin X1, Huang Y1, Nie Z2, Yao S1.
• Biosensors & bioelectronics.Biosens Bioelectron.2016 Dec 15;86:1038-46. doi: 10.1016/j.bios.2016.07.107. Epub 2016 Jul 30.
• Citrate synthase (CS) is one of the key metabolic enzymes in the Krebs tricarboxylic acid (TCA) cycle. It regulates energy generation in mitochondrial respiration by catalysing the reaction between oxaloacetic acid (OAA) and acetyl coenzyme A (Ac-CoA) to generate citrate and coenzyme A (CoA). CS has
• PMID 27501341

• Ancillary contributions of heterologous biotin protein ligase and carbonic anhydrase for CO2 incorporation into 3-hydroxypropionate by metabolically engineered Pyrococcus furiosus.

• Lian H1, Zeldes BM1, Lipscomb GL2, Hawkins AB1, Han Y1, Loder AJ1, Nishiyama D1, Adams MW2, Kelly RM3.
• Biotechnology and bioengineering.Biotechnol Bioeng.2016 Dec;113(12):2652-2660. doi: 10.1002/bit.26033. Epub 2016 Jun 30.
• Acetyl-Coenzyme A carboxylase (ACC), malonyl-CoA reductase (MCR), and malonic semialdehyde reductase (MRS) convert HCO3- and acetyl-CoA into 3-hydroxypropionate (3HP) in the 3-hydroxypropionate/4-hydroxybutyrate carbon fixation cycle resident in the extremely thermoacidophilic archaeon Metallosphaer
• PMID 27315782

• Signal-on CoA-dependent electrochemical biosensor for highly sensitive and label-free detection of Citrate synthase activity.

• Wang Q1, Chen H1, Li Y1, Wang H1, Nie Z2, Hu Y3, Yao S1.
• Talanta.Talanta.2016 Dec 1;161:583-591. doi: 10.1016/j.talanta.2016.08.085. Epub 2016 Aug 31.
• We report here a label-free and sensitive electrochemical method for probing Citrate synthase (CS) activity based on detailed investigations into the nucleic acid-mimicking coordination polymer (CP) formed from the coenzyme A (CoA)-Ag(I) repeat units. Our biosensing approach provides an especial and
• PMID 27769451

Japanese Journal

• Aspirin regulates hepatocellular lipid metabolism by activating AMPK signaling pathway

• , , [他], , , , , ,
• The Journal of Toxicological Sciences 40(1), 127-136, 2015
• … The results demonstrated that aspirin treatment did not regulate the expression of AMPK and its downstream target, Acetyl-Coenzyme A Carboxylase (ACC), but activated the AMPK signaling pathway by promoting the phosphorylation of AMPK and ACC. …
• NAID 130004904029

• 5. 子宮内膜症におけるエピジェネティクス異常の解明(シンポジウム3(生殖・女性ヘルスケア) 子宮内膜症の病因・病態解明と治療戦略,第66回日本産科婦人科学会・学術講演会)

• 奈須 家栄
• 日本産科婦人科學會雜誌 66(12), 2919-2928, 2014-12-01
• … The latter of these two enzymes transfers acetyl groups from acetyl-coenzyme A to lysine residues on the N-terminal region of the histones to activate genetic transcription. … They remove the acetyl groups, restoring the positive charge on lysine residues and thus preventing transcription. …
• NAID 110009896017

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★リンクテーブル★

リンク元	「アセチル補酵素A」「アセチルCoA」
拡張検索	「acetyl-coenzyme A synthetase」「acetyl-coenzyme A」
関連記事	「A」「Ad」「acetyl」

「アセチル補酵素A」

　　[★]

英

acetyl-coenzyme A, acetyl coenzyme A、acetyl-CoA, acetyl CoA

同

アセチルCoA、アセチルコエンザイムA、アセチル-CoA、アセチル-補酵素A

関

補酵素A

「アセチルCoA」

　　[★]

英

acetyl-CoA, acetyl coenzyme A

同

アセチル補酵素A、活性酢酸 active acetate

関

アセチル基

CH3-CO-CoA

「acetyl-coenzyme A synthetase」

　　[★]

• アセチル補酵素A合成酵素、アセチルCoA合成酵素

関

acetate-CoA ligase、acetyl-CoA synthetase

「acetyl-coenzyme A」

　　[★]

英

acetyl coenzyme A

関

アセチルCoA

「A」

　　[★]

• アデニン adenine
• アデノシン adenosine
• アラニン alanine

　 　 　

「Ad」

　　[★]

• アデノウイルス

関

adenoviral、adenovirus

「acetyl」

　　[★]

アセチル

関

Ac