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
CAS Number	992-67-6  Y
3D model (JSmol)	Interactive image
ChemSpider	444072
ECHA InfoCard	100.012.360
MeSH	Crotonyl-coenzyme+A
PubChem CID	592
UNII	Q959BSX9OA  Y
CompTox Dashboard (EPA)	DTXSID30904345
InChI 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
SMILES 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
Chemical formula	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

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. 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. 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

• Crotonic acid
• Glutaryl-CoA dehydrogenase