Chemistry:Crotonyl-CoA

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Crotonyl-CoA
Crotonyl coenzyme A.svg
Names
Preferred 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
3D model (JSmol)
ChemSpider
MeSH Crotonyl-coenzyme+A
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).
Infobox references
Tracking categories (test):

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]

Crotonyl-coA and reductases

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]

Role of Crotonyl-coA in Transcription

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]

References

  1. Ray, Lauren; Valentic, Timothy R; Miyazawa, Takeshi; Withall, David M; Song, Lijiang; Milligan, Jacob C; Osada, Hiroyuki; Takahashi, Shunji et al. (2016). "A crotonyl-CoA reductase-carboxylase independent pathway for assembly of unusual alkylmalonyl-CoA polyketide synthase extender units". Nature Communications 7: 13609. doi:10.1038/ncomms13609. PMID 28000660. Bibcode2016NatCo...713609R. 
  2. "Crotonyl-CoA". https://pubchem.ncbi.nlm.nih.gov/compound/5280381#section=Top. 
  3. 3.0 3.1 3.2 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. http://dx.doi.org/10.1039/c1np00082a. 
  4. 4.0 4.1 Sabari, Benjamin R.; Tang, Zhanyun; Huang, He; Yong-Gonzalez, Vladimir; Molina, Henrik; Kong, Ha Eun; Dai, Lunzhi; Shimada, Miho et al. (2015-04-16). "Intracellular Crotonyl-CoA Stimulates Transcription through p300-Catalyzed Histone Crotonylation" (in English). Molecular Cell 58 (2): 203–215. doi:10.1016/j.molcel.2015.02.029. ISSN 1097-2765. PMID 25818647. 

See also