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Names | |
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IUPAC name
3′-O-Phosphonoadenosine 5′-{[(2R,3S,4R,5R)-5-(6-Amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methyl} O3-{(3R)-4-[(3-{[2-(butanoylsulfanyl)ethyl]amino}-3-oxopropyl)amino]-3-hydroxy-2,2-dimethyl-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)-4-[(3-{[2-(butanoylsulfanyl)ethyl]amino}-3-oxopropyl)amino]-3-hydroxy-2,2-dimethyl-4-oxobutyl} dihydrogen diphosphate | |
Identifiers | |
3D model (
JSmol)
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3DMet | |
ChEBI | |
ChemSpider | |
KEGG | |
MeSH | butyryl-coenzyme+A |
PubChem
CID
|
|
CompTox Dashboard (
EPA)
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|
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Properties | |
C25H42N7O17P3S | |
Molar mass | 837.62 g·mol−1 |
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
|
Butyryl-CoA (or butyryl-coenzyme A, butanoyl-CoA) is an organic coenzyme A-containing derivative of butyric acid. [1] It is a natural product found in many biological pathways, such as fatty acid metabolism ( degradation and elongation), fermentation, and 4-aminobutanoate (GABA) degradation. It mostly participates as an intermediate, a precursor to and converted from crotonyl-CoA. [2] This interconversion is mediated by butyryl-CoA dehydrogenase.
From redox data, butyryl-CoA dehydrogenase shows little to no activity at pH higher than 7.0. This is important as enzyme midpoint potential is at pH 7.0 and at 25 °C. Therefore, changes above from this value will denature the enzyme. [3]
Within the human colon, butyrate helps supply energy to the gut epithelium and helps regulate cell responses. [4]
Butyryl-CoA has a very high calculated potential Gibbs energy, -462.53937 kcal/mol, stored at its bond with CoA. [5]
Butyryl-CoA interconverts to and from 3-oxohexanoyl-CoA by acetyl-CoA acetyltransferase (or thiolase). [6] In terms of organic chemistry, the reaction is the reverse of a Claisen condensation. [7] [8] [9] [10] [11] [12] Subsequently butyryl-CoA is converted into crotonyl-CoA. The conversion is catalyzed by electron-transfer flavoprotein 2,3-oxidoreductase. [13] This enzyme has many synonyms that are orthologous to each other, including butyryl-CoA dehydrogenase, [14] [15] [16] acyl-CoA dehydrogenase, [17] acyl-CoA oxidase, [18] and short-chain 2-methylacyl-CoA dehydrogenase [19]
Butyryl-CoA is an intermediate of the fermentation pathway found in Clostridium kluyveri. [20] [21] [22] This species can ferment acetyl-CoA and succinate into butanoate, extracting energy through the process. [21] [22] The fermentation pathway from ethanol to acetyl-CoA to butanoate is also known as ABE fermentation.
Butyryl-CoA is reduced from crotonyl-CoAcatalyzing by butyryl-CoA dehydrogenase, where two NADH molecules donate four electrons, with two of them reducing ferredoxin ([2Fe-2S] cluster) and the other two reducing crotonyl-CoA into butyryl-CoA. [23] [24] [25] Subsequently, butyryl-CoA is converted into butanoate by propionyl-CoA transferase, which transfers the coenzyme-A group onto an acetate, forming acetyl-CoA. [26] [27]
It is essential in reducing ferredoxins in anaerobic bacteria and archaea so that electron transport phosphorylation and substrate-level phosphorylation can occur with increased efficiency. [28]
Butyryl-CoA is also an intermediate found in 4-aminobutanoate (GABA) degradation. [29] 4-aminobutanoate (GABA) has two fates in this degradation pathway. When discovered in Acetoanaerobium sticklandii and Pseudomonas fluorescens, 4-aminobutanoate was converted into glutamate, which can be deaminated, releasing ammonium. [30] [31] [32]However, in Acetoanaerobium sticklandii and Clostridium aminobutyricum, 4-aminobutanoate was converted into succinate semialdehyde and, through a series of steps via the intermediate of butanoyl-CoA, finally converted into butanoate. [33] [34]
The degradation pathway plays an important role in regulating the concentration of GABA, which is an inhibitory neurotransmitter that reduces neuronal excitability. [35] Dysregulation of GABA degradation can lead to imbalances in neurotransmitter levels, contributing to various neurological disorders such as epilepsy, anxiety, and depression. [36] [37]The reaction mechanism is the same as that in the fermentation pathway, where butyryl-CoA is first reduced from crotonyl-CoA and then converted into butanoate. [29]
Butyryl-CoA acts upon butanol dehydrogenase via competitive inhibition. The adenine moiety can bind butanol dehydrogenase and reduce its activity. [38] The phosphate moiety of butyryl-CoA is found to have inhibitory activities upon its binding with phosphotransbutyrylase. [39]
Butyryl-CoA is also believed to have inhibitory effects on acetyl-CoA acetyltransferase, [40] DL-methylmalonyl-CoA racemase, [41] and glycine N-acyltransferase, [42] however, the specific mechanism remains unknown.
PubChem. "Butyryl-CoA". pubchem.ncbi.nlm.nih.gov. Retrieved 2021-11-18.
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Names | |
---|---|
IUPAC name
3′-O-Phosphonoadenosine 5′-{[(2R,3S,4R,5R)-5-(6-Amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methyl} O3-{(3R)-4-[(3-{[2-(butanoylsulfanyl)ethyl]amino}-3-oxopropyl)amino]-3-hydroxy-2,2-dimethyl-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)-4-[(3-{[2-(butanoylsulfanyl)ethyl]amino}-3-oxopropyl)amino]-3-hydroxy-2,2-dimethyl-4-oxobutyl} dihydrogen diphosphate | |
Identifiers | |
3D model (
JSmol)
|
|
3DMet | |
ChEBI | |
ChemSpider | |
KEGG | |
MeSH | butyryl-coenzyme+A |
PubChem
CID
|
|
CompTox Dashboard (
EPA)
|
|
| |
| |
Properties | |
C25H42N7O17P3S | |
Molar mass | 837.62 g·mol−1 |
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
|
Butyryl-CoA (or butyryl-coenzyme A, butanoyl-CoA) is an organic coenzyme A-containing derivative of butyric acid. [1] It is a natural product found in many biological pathways, such as fatty acid metabolism ( degradation and elongation), fermentation, and 4-aminobutanoate (GABA) degradation. It mostly participates as an intermediate, a precursor to and converted from crotonyl-CoA. [2] This interconversion is mediated by butyryl-CoA dehydrogenase.
From redox data, butyryl-CoA dehydrogenase shows little to no activity at pH higher than 7.0. This is important as enzyme midpoint potential is at pH 7.0 and at 25 °C. Therefore, changes above from this value will denature the enzyme. [3]
Within the human colon, butyrate helps supply energy to the gut epithelium and helps regulate cell responses. [4]
Butyryl-CoA has a very high calculated potential Gibbs energy, -462.53937 kcal/mol, stored at its bond with CoA. [5]
Butyryl-CoA interconverts to and from 3-oxohexanoyl-CoA by acetyl-CoA acetyltransferase (or thiolase). [6] In terms of organic chemistry, the reaction is the reverse of a Claisen condensation. [7] [8] [9] [10] [11] [12] Subsequently butyryl-CoA is converted into crotonyl-CoA. The conversion is catalyzed by electron-transfer flavoprotein 2,3-oxidoreductase. [13] This enzyme has many synonyms that are orthologous to each other, including butyryl-CoA dehydrogenase, [14] [15] [16] acyl-CoA dehydrogenase, [17] acyl-CoA oxidase, [18] and short-chain 2-methylacyl-CoA dehydrogenase [19]
Butyryl-CoA is an intermediate of the fermentation pathway found in Clostridium kluyveri. [20] [21] [22] This species can ferment acetyl-CoA and succinate into butanoate, extracting energy through the process. [21] [22] The fermentation pathway from ethanol to acetyl-CoA to butanoate is also known as ABE fermentation.
Butyryl-CoA is reduced from crotonyl-CoAcatalyzing by butyryl-CoA dehydrogenase, where two NADH molecules donate four electrons, with two of them reducing ferredoxin ([2Fe-2S] cluster) and the other two reducing crotonyl-CoA into butyryl-CoA. [23] [24] [25] Subsequently, butyryl-CoA is converted into butanoate by propionyl-CoA transferase, which transfers the coenzyme-A group onto an acetate, forming acetyl-CoA. [26] [27]
It is essential in reducing ferredoxins in anaerobic bacteria and archaea so that electron transport phosphorylation and substrate-level phosphorylation can occur with increased efficiency. [28]
Butyryl-CoA is also an intermediate found in 4-aminobutanoate (GABA) degradation. [29] 4-aminobutanoate (GABA) has two fates in this degradation pathway. When discovered in Acetoanaerobium sticklandii and Pseudomonas fluorescens, 4-aminobutanoate was converted into glutamate, which can be deaminated, releasing ammonium. [30] [31] [32]However, in Acetoanaerobium sticklandii and Clostridium aminobutyricum, 4-aminobutanoate was converted into succinate semialdehyde and, through a series of steps via the intermediate of butanoyl-CoA, finally converted into butanoate. [33] [34]
The degradation pathway plays an important role in regulating the concentration of GABA, which is an inhibitory neurotransmitter that reduces neuronal excitability. [35] Dysregulation of GABA degradation can lead to imbalances in neurotransmitter levels, contributing to various neurological disorders such as epilepsy, anxiety, and depression. [36] [37]The reaction mechanism is the same as that in the fermentation pathway, where butyryl-CoA is first reduced from crotonyl-CoA and then converted into butanoate. [29]
Butyryl-CoA acts upon butanol dehydrogenase via competitive inhibition. The adenine moiety can bind butanol dehydrogenase and reduce its activity. [38] The phosphate moiety of butyryl-CoA is found to have inhibitory activities upon its binding with phosphotransbutyrylase. [39]
Butyryl-CoA is also believed to have inhibitory effects on acetyl-CoA acetyltransferase, [40] DL-methylmalonyl-CoA racemase, [41] and glycine N-acyltransferase, [42] however, the specific mechanism remains unknown.
PubChem. "Butyryl-CoA". pubchem.ncbi.nlm.nih.gov. Retrieved 2021-11-18.