Crotonyl_CoA
Crotonyl-CoA
Chemical compound
Crotonyl-coenzyme A is an intermediate in the fermentation of butyric acid, and in the metabolism of lysine and tryptophan.[1] It is important in the metabolism of fatty acids and amino acids.[2]
| Names | |
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| IUPAC name
3′-O-Phosphonoadenosine 5′-[(3R)-4-({3-[(2-{[(2E)-but-2-enoyl]sulfanyl}ethyl)amino]-3-oxopropyl}amino)-3-hydroxy-2,2-dimethyl-4-oxobutyl dihydrogen diphosphate] | |
| Systematic IUPAC name
[(2R,3S,4R,5R)-5-(6-Amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methyl (3R)-4-({3-[(2-{[(2E)-but-2-enoyl]sulfanyl}ethyl)amino]-3-oxopropyl}amino)-3-hydroxy-2,2-dimethyl-4-oxobutyl dihydrogen diphosphate | |
| Identifiers | |
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3D model (JSmol) |
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| ChemSpider | |
| ECHA InfoCard | 100.012.360  |
| MeSH | Crotonyl-coenzyme+A |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C25H40N7O17P3S | |
| Molar mass | 835.609 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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Before a 2007 report by Alber and coworkers, crotonyl-coA carboxylases and reductases (CCRs) were known for reducing crotonyl-coA to butyryl-coA.[3] A report by Alber and coworkers concluded that a specific CCR homolog was able to reduce crotonyl-coA to (2S)-ethyl malonyl-coA which was a favorable reaction.[3] The specific CCR homolog came from the bacterium Rhodobacter sphaeroides.[3]
Post-translational modification of histones either by acetylation or crotonylation is important for the active transcription of genes.[4] Histone crotonylation is regulated by the concentration of crotonyl-coA which can change based on environmental cell conditions or genetic factors.[4]
- Ray, Lauren; Valentic, Timothy R; Miyazawa, Takeshi; Withall, David M; Song, Lijiang; Milligan, Jacob C; Osada, Hiroyuki; Takahashi, Shunji; Tsai, Shiou-Chuan; Challis, Gregory L (2016). "A crotonyl-CoA reductase-carboxylase independent pathway for assembly of unusual alkylmalonyl-CoA polyketide synthase extender units". Nature Communications. 7: 13609. Bibcode:2016NatCo...713609R. doi:10.1038/ncomms13609. PMC 5187497. PMID 28000660.
- Wilson, Micheal C.; Moore, Bradley S. (2012). "Beyond ethylmalonyl-CoA: The functional role of crotonyl-CoAcarboxylase/reductase homologs in expanding polyketide diversity". Nat. Prod. Rep. 29 (1): 72–86. doi:10.1039/c1np00082a. ISSN 0265-0568. PMID 22124767.
- Sabari, Benjamin R.; Tang, Zhanyun; Huang, He; Yong-Gonzalez, Vladimir; Molina, Henrik; Kong, Ha Eun; Dai, Lunzhi; Shimada, Miho; Cross, Justin R.; Zhao, Yingming; Roeder, Robert G. (2015-04-16). "Intracellular Crotonyl-CoA Stimulates Transcription through p300-Catalyzed Histone Crotonylation". Molecular Cell. 58 (2): 203–215. doi:10.1016/j.molcel.2015.02.029. ISSN 1097-2765. PMC 4501262. PMID 25818647.
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