Butyryl-CoA - Wiki slovník

Butyryl-CoA
Names
	IUPAC name 3′-O-Phosphonoadenosine 5′-{methyl} O3-{(3R)-4-2-(butanoylsulfanyl)ethylamino}-3-oxopropyl)amino-3-hydroxy-2,2-dimethyl-4-oxobutyl dihydrogen diphosphate}
	Systematic IUPAC name O1-{(2R,3S,4R,5R)-5-(6-Amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-ylmethyl} O3-{(3R)-4-(3-{2-(butanoylsulfanyl)ethylamino}-3-oxopropyl)amino-3-hydroxy-2,2-dimethyl-4-oxobutyl} dihydrogen diphosphate
Identifiers
CAS Number	2140-48-9 ;
3D model (JSmol)	Interactive image;
3DMet	B04811;
ChEBI	CHEBI:15517;
ChemSpider	260 ; 388318 {(2R,3S,4R,5R)-5-yl,-2-meth,-4-hydrox,-3-yl} ; 5292369 {(2R,3R,5R)-5-yl,-2-({{(3S)-3-hydrox-ox}-phosph-ox}-meth),-3-yl} ;
KEGG	C00136 ;
MeSH	butyryl-coenzyme+A
PubChem CID	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};
CompTox Dashboard (EPA)	DTXSID70943955 ;
	InChI 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) Key: CRFNGMNYKDXRTN-UHFFFAOYSA-N ;
	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;
Properties
Chemical formula	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]

Referencesedit

^ "Human Metabolome Database: Showing metabocard for Butyryl-CoA (HMDB0001088)".
^ 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.
^ 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.
^ 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.
^ 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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[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] 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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Further readingedit

See alsoedit

Referencesedit

Names

IUPAC name 3′-O-Phosphonoadenosine 5′-{methyl} O³-{(3R)-4-2-(butanoylsulfanyl)ethylamino}-3-oxopropyl)amino-3-hydroxy-2,2-dimethyl-4-oxobutyl dihydrogen diphosphate}
Systematic IUPAC name O¹-{(2R,3S,4R,5R)-5-(6-Amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-ylmethyl} O³-{(3R)-4-(3-{2-(butanoylsulfanyl)ethylamino}-3-oxopropyl)amino-3-hydroxy-2,2-dimethyl-4-oxobutyl} dihydrogen diphosphate
Identifiers
CAS Number	2140-48-9^N
3D model (JSmol)	Interactive image
3DMet	B04811
ChEBI	CHEBI:15517
ChemSpider	260^Y 388318 {(2R,3S,4R,5R)-5-yl,-2-meth,-4-hydrox,-3-yl}^Y 5292369 {(2R,3R,5R)-5-yl,-2-({{(3S)-3-hydrox-ox}-phosph-ox}-meth),-3-yl}^Y
KEGG	C00136^Y
MeSH	butyryl-coenzyme+A
PubChem CID	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}
CompTox Dashboard (EPA)	DTXSID70943955
InChI 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)^Y Key: CRFNGMNYKDXRTN-UHFFFAOYSA-N^Y
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
Properties
Chemical formula	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