Chemistry:Butyryl-CoA
![Stereo skeletal formula of tetradeprotonated butyryl-coA ({[(2R,3S,4R,5R)-5-yl,-2-meth,-4-hydrox,-3-yl]})](/wiki/File:Butyryl_coenzyme_A.svg)
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| Names | |
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| IUPAC name
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}
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| Systematic 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)
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| 3DMet | |
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| KEGG | |
| MeSH | butyryl-coenzyme+A |
PubChem CID
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| 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-containing derivative of butyric acid.[1] It is acted upon by butyryl-CoA dehydrogenase and an intermediary compound of ABE fermentation.
Butyryl-CoA is a precursor to and converted from crotonyl-CoA. This interconversion is mediated by butyryl-COA dehydrogenase. FADH- is the hydride to crotonyl-CoA and FAD+ is the hydride acceptor.[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]
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]
Within the human colon, butyrate helps supply energy to the gut epithelium and helps regulate cell responses.[5]
Further reading
PubChem. "Butyryl-CoA" (in en). https://pubchem.ncbi.nlm.nih.gov/compound/122283.
See also
References
- ↑ "Human Metabolome Database: Showing metabocard for Butyryl-CoA (HMDB0001088)". http://www.hmdb.ca/metabolites/HMDB0001088.
- ↑ "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. February 2014. doi:10.1074/jbc.M113.521013. PMID 24379410.
- ↑ "The semiquinone swing in the bifurcating electron transferring flavoprotein/butyryl-CoA dehydrogenase complex from Clostridium difficile". Nature Communications 8 (1): 1577. November 2017. doi:10.1038/s41467-017-01746-3. PMID 29146947. Bibcode: 2017NatCo...8.1577D.
- ↑ "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. February 2013. doi:10.1007/s12010-012-0060-7. PMID 23292245.
- ↑ "Diversity of human colonic butyrate-producing bacteria revealed by analysis of the butyryl-CoA:acetate CoA-transferase gene". Environmental Microbiology 12 (2): 304–314. February 2010. doi:10.1111/j.1462-2920.2009.02066.x. PMID 19807780.
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