Butyryl-CoA

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Butyryl-CoA
Stereo skeletal formula of tetradeprotonated butyryl-coA ({[(2R,3S,4R,5R)-5-yl,-2-meth,-4-hydrox,-3-yl]})
Names
Preferred IUPAC name
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
Identifiers
3D model (JSmol)
3DMet
ChEBI
ChemSpider
  • 260 checkY
  • 388318 {[(2R,3S,4R,5R)-5-yl,-2-meth,-4-hydrox,-3-yl]} checkY
  • 5292369 {[(2R,3R,5R)-5-yl,-2-({[{[(3S)-3-hydrox]-ox}-phosph]-ox}-meth),-3-yl]} checkY
KEGG
MeSH butyryl-coenzyme+A
  • 265
  • 25201345 {[(2R,5R)-5-yl,-2-({[{[(3R)-3-hydrox]-ox}-phosph]-ox}-meth),-3-yl]}
  • 439173 {[(2R,3S,4R,5R)-5-yl,-2-meth,-4-hydrox,-3-yl]}
  • 46907881 {[(2R,3R,5R)-5-yl,-2-({[{[(3R)-3-hydrox]-ox}-phosph]-ox}-meth),-3-yl]}
  • 6917112 {[(2R,3R,5R)-5-yl,-2-({[{[(3S)-3-hydrox]-ox}-phosph]-ox}-meth),-3-yl]}
  • InChI=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) checkY
    Key: CRFNGMNYKDXRTN-UHFFFAOYSA-N checkY
  • 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
Properties
C25H42N7O17P3S
Molar mass 837.62 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Butyryl-coenzyme A (or butyryl-CoA) is the coenzyme A-activated form of butyric acid.[1]

It is acted upon by butyryl-CoA dehydrogenase.

It is an intermediary compound of ABE fermentation

Butyryl-CoA is also converted from Crotonyl-CoA. This occurs when FADH- transfers a hydride to crotonyl-CoA.[2] It is essential in reducing ferredoxins in anaerobic bacteria and archaea so that electron transport phosphorylation and substrate level phosphorylation can occur with increased efficiency.[3]

Butyryl-COA dehydrogenase Oxidation-Reduction reaction consists of 2 electron transfer with 1 proton exchange. Ideally, this will occur between pH 5.5 and 7 for optimal reaction. In this range is where the enzyme is most stable.

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 degrees C. Therefore, changes above from this value will denature the enzyme.[4]

The molecule Butyryl-CoA has the following functional groups in the structure: phosphate group, hydroxyl groups, phosphoryl groups, amine group, purine group, butane groups, methyl groups, sulfide group. The ones worth noting are the ones above. As some of these groups carry negative charge. This has a change onto the compounds pH, 3D structure, mass and bond angles.[5]Within the human colon, butyrate helps supply energy to the gut epithelium and helps regulate cell responses. [6]

See also[]

References[]

  1. ^ "Human Metabolome Database: Showing metabocard for Butyryl-CoA (HMDB0001088)".
  2. ^ Chowdhury NP, Mowafy AM, Demmer JK, Upadhyay V, Koelzer S, Jayamani E, et al. (February 2014). "Studies on the mechanism of electron bifurcation catalyzed by electron transferring flavoprotein (Etf) and butyryl-CoA dehydrogenase (Bcd) of Acidaminococcus fermentans". The Journal of Biological Chemistry. 289 (8): 5145–5157. doi:10.1074/jbc.M113.521013. PMC 3931072. PMID 24379410.
  3. ^ Demmer JK, Pal Chowdhury N, Selmer T, Ermler U, Buckel W (November 2017). "The semiquinone swing in the bifurcating electron transferring flavoprotein/butyryl-CoA dehydrogenase complex from Clostridium difficile". Nature Communications. 8 (1): 1577. Bibcode:2017NatCo...8.1577D. doi:10.1038/s41467-017-01746-3. PMC 5691135. PMID 29146947.
  4. ^ Berzin V, Tyurin M, Kiriukhin M (February 2013). "Selective n-butanol production by Clostridium sp. MTButOH1365 during continuous synthesis gas fermentation due to expression of synthetic thiolase, 3-hydroxy butyryl-CoA dehydrogenase, crotonase, butyryl-CoA dehydrogenase, butyraldehyde dehydrogenase, and NAD-dependent butanol dehydrogenase". Applied Biochemistry and Biotechnology. 169 (3): 950–959. doi:10.1007/s12010-012-0060-7. PMID 23292245. S2CID 22534861.
  5. ^ PubChem. "Butyryl-CoA". pubchem.ncbi.nlm.nih.gov. Retrieved 2021-11-18.
  6. ^ Louis P, Young P, Holtrop G, Flint HJ (February 2010). "Diversity of human colonic butyrate-producing bacteria revealed by analysis of the butyryl-CoA:acetate CoA-transferase gene". Environmental Microbiology. 12 (2): 304–314. doi:10.1111/j.1462-2920.2009.02066.x. PMID 19807780.
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