Benzoyl-CoA: Difference between revisions

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	{{chembox		{{chembox
			\| Verifiedfields = changed
⚫	\| verifiedrevid = ~~367246180~~
			\| Watchedfields = changed
		⚫	\| verifiedrevid = 432092180
	\| Name = Benzoyl-Coenzyme A		\| Name = Benzoyl-Coenzyme A
	\| ImageFile = Benzoyl-CoA.svg		\| ImageFile = Benzoyl-CoA.svg
Line 8:		Line 10:
	\| IUPACName =		\| IUPACName =
	\| OtherNames = benzoyl-S-CoA<br>S-Benzoate coenzyme A		\| OtherNames = benzoyl-S-CoA<br>S-Benzoate coenzyme A
	\|Section1= {{Chembox Identifiers		\|Section1={{Chembox Identifiers
	\| CASNo = 102185-37-5		\| CASNo = 102185-37-5
	\| CASNo_Ref =		\| CASNo_Ref = {{cascite\|correct\|??}}
	\| ~~CASOther~~ =		\| CASNoOther =
			\| UNII_Ref = {{fdacite\|correct\|FDA}}
			\| UNII = 6ZL6G9S5GY
	\| PubChem = 25245721		\| PubChem = 25245721
			\| ChemSpiderID_Ref = {{chemspidercite\|changed\|chemspider}}
	\| SMILES =
	\| ~~InChI~~ =		\| ChemSpiderID = 7822142
			\| ChEBI = 15515
			\| SMILES = CC(C)(COP(=O)(O)OP(=O)(O)OC1(((O1)N2C=NC3=C(N=CN=C32)N)O)OP(=O)(O)O)(C(=O)NCCC(=O)NCCSC(=O)C4=CC=CC=C4)O
			\| InChI = 1/C28H40N7O17P3S/c1-28(2,22(38)25(39)31-9-8-18(36)30-10-11-56-27(40)16-6-4-3-5-7-16)13-49-55(46,47)52-54(44,45)48-12-17-21(51-53(41,42)43)20(37)26(50-17)35-15-34-19-23(29)32-14-33-24(19)35/h3-7,14-15,17,20-22,26,37-38H,8-13H2,1-2H3,(H,30,36)(H,31,39)(H,44,45)(H,46,47)(H2,29,32,33)(H2,41,42,43)/t17-,20-,21-,22+,26-/m1/s1
			\| InChIKey = VEVJTUNLALKRNO-TYHXJLICBE
			\| StdInChI_Ref = {{stdinchicite\|changed\|chemspider}}
			\| StdInChI = 1S/C28H40N7O17P3S/c1-28(2,22(38)25(39)31-9-8-18(36)30-10-11-56-27(40)16-6-4-3-5-7-16)13-49-55(46,47)52-54(44,45)48-12-17-21(51-53(41,42)43)20(37)26(50-17)35-15-34-19-23(29)32-14-33-24(19)35/h3-7,14-15,17,20-22,26,37-38H,8-13H2,1-2H3,(H,30,36)(H,31,39)(H,44,45)(H,46,47)(H2,29,32,33)(H2,41,42,43)/t17-,20-,21-,22+,26-/m1/s1
			\| StdInChIKey_Ref = {{stdinchicite\|changed\|chemspider}}
			\| StdInChIKey = VEVJTUNLALKRNO-TYHXJLICSA-N
	\| MeSHName =		\| MeSHName =
	}}		}}
	\|Section2= {{Chembox Properties		\|Section2={{Chembox Properties
	\| Formula = C<sub>28</sub>H<sub>36</sub>N<sub>7</sub>O<sub>17</sub>P<sub>3</sub>S<sup>-4</sup>		\| Formula = C<sub>28</sub>H<sub>36</sub>N<sub>7</sub>O<sub>17</sub>P<sub>3</sub>S<sup>−4</sup>
	\| MolarMass = 867.60 g/mol		\| MolarMass = 867.60 g/mol
	\| ExactMass = 867.110123 u
	\| Appearance =		\| Appearance =
	\| Density =		\| Density =
	\| MeltingPt = ~~<!-- °C -->~~		\| MeltingPt =
	\| BoilingPt = ~~<!-- °C -->~~		\| BoilingPt =
	\| Solubility =		\| Solubility =
	}}		}}
	}}		}}
			'''Benzoyl-CoA''' is the thioester derived from ] and ]. The term benzoyl-CoA also include diverse conjugates of coenzyme A and aromatic carboxylic acids. Benzoate, ], ], ], ], ], ], ], ], and ] are all metabolized to benzoyl-CoA. Additionally,
	'''Benzoyl-CoA''' is a molecule implied in the activity of the different enzymes ], ], ], ], ], ], ], ], ] and ].
			], ], ], ], ], ], and ] are suspected to be processed similarly.<ref name= Porter/>

			==As substrate for reductases==
⚫	It is a substrate in the formation of ]s in '']'' by ] condensing a molecule of benzoyl-CoA with three ] yielding to ]. This intermediate is subsequently converted by a ], a cytochrome P450 monooxygenase, leading to the formation of ]<ref></ref>.
			]
			Benzoyl-CoA is a substrate for diverse reductases:<ref name= Porter>{{cite journal \|pmid=24767428 \|date=2014 \|last1=Porter \|first1=A. W. \|last2=Young \|first2=L. Y. \|title=Benzoyl-CoA, a Universal Biomarker for Anaerobic Degradation of Aromatic Compounds \|journal=Advances in Applied Microbiology \|volume=88 \|pages=167–203 \|doi=10.1016/B978-0-12-800260-5.00005-X \|isbn=978-0-12-800260-5 }}</ref> ], ], ], ], ], ], ], ], ] and ]. Benzoyl-CoA reductase converts benzoyl-CoA to cyclohex-1,5-diene-1-carbonyl-CoA, which is susceptible to hydrolysis, eventually giving ]. In this way, many aromatic compounds are biodegraded.

			==As a benzoyl donor==
⚫	==References==
		⚫	Benzoyl-CoA is a benzoyl transfer agent for the ] of ]. Benzoyl-CoA is a substrate in the formation of ]s in '']'' by ], condensing a molecule of benzoyl-CoA with three ], yielding to 2,4,6-trihydroxybenzophenone. This intermediate is subsequently converted by a benzophenone 3′-hydroxylase, a ] monooxygenase, leading to the formation of 2,3′,4,6-tetrahydroxybenzophenone.<ref>, {{doi\|10.1016/S0014-5793(97)01507-X}}</ref>
⚫	{{reflist}}

			Benzoyl-CoA is a substrate of benzoyl-CoA reductase. This enzyme is responsible in part for the reductive ] of aryl compounds mediated by bacteria under anaerobic conditions.<ref>Matthias Boll , Georg Fuchs , Johann Heider "Anaerobic oxidation of aromatic compounds and hydrocarbons" Current Opinion in Chemical Biology 2002 Volume 6, pp. 604–611. {{doi\|10.1016/S1367-5931(02)00375-7}}</ref>
	]

		⚫	==References==
	{{metabolism-stub}}
		⚫	{{reflist}}

	]		]

Latest revision as of 17:13, 22 January 2024

Benzoyl-Coenzyme A
Names

Other names benzoyl-S-CoA S-Benzoate coenzyme A
Identifiers
CAS Number	102185-37-5
3D model (JSmol)	Interactive image
ChEBI	CHEBI:15515
ChemSpider	7822142
PubChem CID	25245721
UNII	6ZL6G9S5GY
CompTox Dashboard (EPA)	DTXSID80585082
InChI InChI=1S/C28H40N7O17P3S/c1-28(2,22(38)25(39)31-9-8-18(36)30-10-11-56-27(40)16-6-4-3-5-7-16)13-49-55(46,47)52-54(44,45)48-12-17-21(51-53(41,42)43)20(37)26(50-17)35-15-34-19-23(29)32-14-33-24(19)35/h3-7,14-15,17,20-22,26,37-38H,8-13H2,1-2H3,(H,30,36)(H,31,39)(H,44,45)(H,46,47)(H2,29,32,33)(H2,41,42,43)/t17-,20-,21-,22+,26-/m1/s1Key: VEVJTUNLALKRNO-TYHXJLICSA-N InChI=1/C28H40N7O17P3S/c1-28(2,22(38)25(39)31-9-8-18(36)30-10-11-56-27(40)16-6-4-3-5-7-16)13-49-55(46,47)52-54(44,45)48-12-17-21(51-53(41,42)43)20(37)26(50-17)35-15-34-19-23(29)32-14-33-24(19)35/h3-7,14-15,17,20-22,26,37-38H,8-13H2,1-2H3,(H,30,36)(H,31,39)(H,44,45)(H,46,47)(H2,29,32,33)(H2,41,42,43)/t17-,20-,21-,22+,26-/m1/s1Key: VEVJTUNLALKRNO-TYHXJLICBE
SMILES CC(C)(COP(=O)(O)OP(=O)(O)OC1(((O1)N2C=NC3=C(N=CN=C32)N)O)OP(=O)(O)O)(C(=O)NCCC(=O)NCCSC(=O)C4=CC=CC=C4)O
Properties
Chemical formula	C₂₈H₃₆N₇O₁₇P₃S
Molar mass	867.60 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). N verify (what is ?) Infobox references

Chemical compound

Benzoyl-CoA is the thioester derived from benzoic acid and coenzyme A. The term benzoyl-CoA also include diverse conjugates of coenzyme A and aromatic carboxylic acids. Benzoate, vanillin, anthranilic acid, 4-ethylphenol, p-cresol, phenol, aniline, terephthalic acid, [3-hydroxybenzoic acid, and phenylalanine are all metabolized to benzoyl-CoA. Additionally, cinnamic acid, p-coumaric acid, ferulic acid, toluene, caffeic acid, benzyl alcohol, and mandelic acid are suspected to be processed similarly.

As substrate for reductases

Benzoyl-CoA is a substrate for diverse reductases: 4-hydroxybenzoyl-CoA reductase, benzoyl-CoA reductase, benzoyl-CoA 3-monooxygenase, benzoate-CoA ligase, 2alpha-hydroxytaxane 2-O-benzoyltransferase, anthranilate N-benzoyltransferase, biphenyl synthase, glycine N-benzoyltransferase, ornithine N-benzoyltransferase and phenylglyoxylate dehydrogenase (acylating). Benzoyl-CoA reductase converts benzoyl-CoA to cyclohex-1,5-diene-1-carbonyl-CoA, which is susceptible to hydrolysis, eventually giving acetyl coenzyme A. In this way, many aromatic compounds are biodegraded.

As a benzoyl donor

Benzoyl-CoA is a benzoyl transfer agent for the biosynthesis of hippuric acid. Benzoyl-CoA is a substrate in the formation of xanthonoids in Hypericum androsaemum by benzophenone synthase, condensing a molecule of benzoyl-CoA with three malonyl-CoA, yielding to 2,4,6-trihydroxybenzophenone. This intermediate is subsequently converted by a benzophenone 3′-hydroxylase, a cytochrome P450 monooxygenase, leading to the formation of 2,3′,4,6-tetrahydroxybenzophenone.

Benzoyl-CoA is a substrate of benzoyl-CoA reductase. This enzyme is responsible in part for the reductive dearomatization of aryl compounds mediated by bacteria under anaerobic conditions.

References

^ Porter, A. W.; Young, L. Y. (2014). "Benzoyl-CoA, a Universal Biomarker for Anaerobic Degradation of Aromatic Compounds". Advances in Applied Microbiology. 88: 167–203. doi:10.1016/B978-0-12-800260-5.00005-X. ISBN 978-0-12-800260-5. PMID 24767428.
Alternative pathways of xanthone biosynthesis in cell cultures of Hypericum androsaemum L. Werner Schmidt and Ludger Beerhues, FEBS Letters, Volume 420, Issues 2-3, 29 December 1997, Pages 143-146, doi:10.1016/S0014-5793(97)01507-X
Matthias Boll , Georg Fuchs , Johann Heider "Anaerobic oxidation of aromatic compounds and hydrocarbons" Current Opinion in Chemical Biology 2002 Volume 6, pp. 604–611. doi:10.1016/S1367-5931(02)00375-7

Category:

Thioesters of coenzyme A