Crotonyl-CoA

Crotonyl-CoA
Names
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
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.012.360 Edit this at Wikidata
MeSH Crotonyl-coenzyme+A
UNII
  • InChI=1/C36H46N4O7S2/c1-25(2)24-40(49(45,46)30-19-15-27(4)16-20-30)34(36(42)47-5)12-8-9-21-37-35(41)33(22-28-23-38-32-11-7-6-10-31(28)32)39-48(43,44)29-17-13-26(3)14-18-29/h6-7,10-11,13-20,23,25,33-34,38-39H,8-9,12,21-22,24H2,1-5H3,(H,37,41)/t33-,34-/m0/s1
    Key: KDDJMRASDNUVJO-HEVIKAOCBM
  • CC=CC(=O)SCCNC(=O)CCNC(=O)C(C(C)(C)COP(=O)(O)OP(=O)(O)OCC1C(C(C(O1)N2C=NC3=C(N=CN=C32)N)O)OP(=O)(O)O)O
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).

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; 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.
  2. ^ "Crotonyl-CoA".
  3. ^ a b c 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.
  4. ^ a b 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.

See also


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