Crotonyl-CoA - Misplaced Pages

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Crotonyl-CoA
Names

IUPAC name 3′-O-Phosphonoadenosine 5′-sulfanyl}ethyl)amino]-3-oxopropyl}amino)-3-hydroxy-2,2-dimethyl-4-oxobutyl dihydrogen diphosphate]
Systematic IUPAC name methyl (3R)-4-({3-sulfanyl}ethyl)amino]-3-oxopropyl}amino)-3-hydroxy-2,2-dimethyl-4-oxobutyl dihydrogen diphosphate
Identifiers
CAS Number	992-67-6
3D model (JSmol)	Interactive image
ChemSpider	444072
ECHA InfoCard	100.012.360
MeSH	Crotonyl-coenzyme+A
PubChem CID	592
UNII	Q959BSX9OA
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/s1Key: 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 , 100 kPa). Infobox references

Chemical compound

Crotonyl-coenzyme A is an intermediate in the fermentation of butyric acid, and in the metabolism of lysine and tryptophan. It is important in the metabolism of fatty acids and amino acids.

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. 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. The specific CCR homolog came from the bacterium Rhodobacter sphaeroides.

Role of Crotonyl-coA in Transcription

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

References

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.
"Crotonyl-CoA".
^ 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.

lysine→	Saccharopine Allysine α-Aminoadipic acid 2-Oxoadipic acid Glutaryl-CoA Glutaconyl-CoA Crotonyl-CoA β-Hydroxybutyryl-CoA
leucine→	β-Hydroxy β-methylbutyric acid β-Hydroxy β-methylbutyryl-CoA Isovaleryl-CoA α-Ketoisocaproic acid β-Ketoisocaproic acid β-Ketoisocaproyl-CoA β-Leucine β-Methylcrotonyl-CoA β-Methylglutaconyl-CoA β-Hydroxy β-methylglutaryl-CoA
tryptophan→alanine→	N′-Formylkynurenine Kynurenine Anthranilic acid 3-Hydroxykynurenine 3-Hydroxyanthranilic acid 2-Amino-3-carboxymuconic semialdehyde 2-Aminomuconic semialdehyde 2-Aminomuconic acid Glutaryl-CoA

G→pyruvate→
citrate

glycine→
serine→

3-Phosphoglyceric acid

G→glutamate→
α-ketoglutarate

histidine→	Urocanic acid Imidazol-4-one-5-propionic acid Formiminoglutamic acid Glutamate-1-semialdehyde
proline→	1-Pyrroline-5-carboxylic acid
arginine→	Agmatine Ornithine Citrulline Cadaverine Putrescine
other	cysteine+glutamate→glutathione: γ-Glutamylcysteine

G→propionyl-CoA→
succinyl-CoA

valine→	α-Ketoisovaleric acid Isobutyryl-CoA Methacrylyl-CoA 3-Hydroxyisobutyryl-CoA 3-Hydroxyisobutyric acid 2-Methyl-3-oxopropanoic acid
isoleucine→	2,3-Dihydroxy-3-methylpentanoic acid 2-Methylbutyryl-CoA Tiglyl-CoA 2-Methylacetoacetyl-CoA
methionine→	generation of homocysteine: S-Adenosyl methionine S-Adenosyl-L-homocysteine Homocysteine conversion to cysteine: Cystathionine α-Ketobutyric acid + Cysteine
threonine→	α-Ketobutyric acid
propionyl-CoA→	Methylmalonyl-CoA

G→fumarate

phenylalanine→tyrosine→	4-Hydroxyphenylpyruvic acid Homogentisic acid 4-Maleylacetoacetic acid

G→oxaloacetate

see urea cycle

Other

Cysteine metabolism	Cysteine sulfinic acid

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Categories:

Crotonyl-coA and reductases

Role of Crotonyl-coA in Transcription

References

See also