Chemistry:Crotonyl-CoA

From HandWiki

Crotonyl-coenzyme A (crotonyl-CoA) 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 is also involved in β-oxidation, where it is formed from butyryl-CoA through the action of acyl-CoA dehydrogenases, linking fatty acid breakdown to cellular energy production.[3]

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.[4] 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.[4] The specific CCR homolog came from the bacterium Rhodobacter sphaeroides.[4] Crotonyl-CoA reductases belong to a broader class of enzymes that catalyze reduction reactions involving coenzyme A thioesters, often contributing to the biosynthesis of complex metabolites in microorganisms.[4] These enzymes are particularly important in metabolic pathways that generate precursors for polyketide synthesis and other secondary metabolites.[4]

Role of crotonyl-CoA in transcription

Post-translational modification of histones either by acetylation or crotonylation is important for the active transcription of genes.[5] Histone crotonylation is regulated by the concentration of crotonyl-CoA which can change based on environmental cell conditions or genetic factors.[5]

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. doi:10.1038/ncomms13609. PMID 28000660. Bibcode2016NatCo...713609R. 
  2. "Crotonyl-CoA". https://pubchem.ncbi.nlm.nih.gov/compound/5280381#section=Top. 
  3. Nelson, David L. (2021). Lehninger Principles of Biochemistry. 
  4. 4.0 4.1 4.2 4.3 4.4 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. 
  5. 5.0 5.1 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