butyryl-CoA

Butyryl-CoA (or butyryl-coenzyme A, butanoyl-CoA) is an organic coenzyme A-containing derivative of butyric acid. It is a natural product found in many biological pathways, such as fatty acid metabolism (degradation and elongation), fermentation, and 4-aminobutanoate (GABA) degradation. It mostly participates as an intermediate, a precursor to and converted from crotonyl-CoA. This interconversion is mediated by butyryl-CoA dehydrogenase.

Article

8 sections

Contents

Reaction
Fatty acid metabolism
Fermentation
4-Aminobutanoate (GABA) degradation
Regulation
See also
References
Further reading

{{Chembox | ImageFile = Butyryl coenzyme A.svg | ImageFile_Ref = | ImageSize = 244 | ImageName = Stereo skeletal formula of tetradeprotonated butyryl-coA ({[(2R,3S,4R,5R)-5-yl,-2-meth,-4-hydrox,-3-yl]}) | IUPACName = 3′-O-Phosphonoadenosine 5′-{[(2R,3S,4R,5R)-5-(6-Amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methyl} O3-{(3R)-4-[(3-{[2-(butanoylsulfanyl)ethyl]amino}-3-oxopropyl)amino]-3-hydroxy-2,2-dimethyl-4-oxobutyl dihydrogen diphosphate} | SystematicName = O1-{[(2R,3S,4R,5R)-5-(6-Amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methyl} O3-{(3R)-4-[(3-{[2-(butanoylsulfanyl)ethyl]amino}-3-oxopropyl)amino]-3-hydroxy-2,2-dimethyl-4-oxobutyl} dihydrogen diphosphate |Section1={{Chembox Identifiers | CASNo = 2140-48-9 | CASNo_Ref = | PubChem = 265 | PubChem1 = 25201345 | PubChem1_Comment = {[(2R,5R)-5-yl,-2-({[{[(3R)-3-hydrox]-ox}-phosph]-ox}-meth),-3-yl]} | PubChem2 = 439173 | PubChem2_Comment = {[(2R,3S,4R,5R)-5-yl,-2-meth,-4-hydrox,-3-yl]} | PubChem3 = 46907881 | PubChem3_Comment = {[(2R,3R,5R)-5-yl,-2-({[{[(3R)-3-hydrox]-ox}-phosph]-ox}-meth),-3-yl]} | PubChem4 = 6917112 | PubChem4_Comment = {[(2R,3R,5R)-5-yl,-2-({[{[(3S)-3-hydrox]-ox}-phosph]-ox}-meth),-3-yl]} | ChemSpiderID = 260 | ChemSpiderID_Ref = | ChemSpiderID1 = 388318 | ChemSpiderID1_Ref = | ChemSpiderID1_Comment = {[(2R,3S,4R,5R)-5-yl,-2-meth,-4-hydrox,-3-yl]} | ChemSpiderID2 = 5292369 | ChemSpiderID2_Ref = | ChemSpiderID2_Comment = {[(2R,3R,5R)-5-yl,-2-({[{[(3S)-3-hydrox]-ox}-phosph]-ox}-meth),-3-yl]} | KEGG = C00136 | KEGG_Ref = | MeSHName = butyryl-coenzyme+A | ChEBI = 15517 | 3DMet = B04811 | SMILES = CCCC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OCC1OC(C(O)C1OP(O)(O)=O)N1C=NC2=C(N)N=CN=C12 | StdInChI = 1S/C25H42N7O17P3S/c1-4-5-16(34)53-9-8-27-15(33)6-7-28-23(37)20(36)25(2,3)11-46-52(43,44)49-51(41,42)45-10-14-19(48-50(38,39)40)18(35)24(47-14)32-13-31-17-21(26)29-12-30-22(17)32/h12-14,18-20,24,35-36H,4-11H2,1-3H3,(H,27,33)(H,28,37)(H,41,42)(H,43,44)(H2,26,29,30)(H2,38,39,40) | StdInChI_Ref = | StdInChIKey = CRFNGMNYKDXRTN-UHFFFAOYSA-N | StdInChIKey_Ref = }} |Section2= }} Butyryl-CoA (or butyryl-coenzyme A, butanoyl-CoA) is an organic coenzyme A-containing derivative of butyric acid. It is a natural product found in many biological pathways, such as fatty acid metabolism (degradation and elongation), fermentation, and 4-aminobutanoate (GABA) degradation. It mostly participates as an intermediate, a precursor to and converted from crotonyl-CoA. This interconversion is mediated by butyryl-CoA dehydrogenase.

From redox data, butyryl-CoA dehydrogenase shows little to no activity at pH higher than 7.0. This is important as enzyme midpoint potential is at pH 7.0 and at 25 °C. Therefore, changes above from this value will denature the enzyme.