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{{chembox |
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{{chembox |
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| Verifiedfields = changed |
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| Watchedfields = changed |
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| verifiedrevid = 432092180 |
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| Name = Benzoyl-Coenzyme A |
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| Name = Benzoyl-Coenzyme A |
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| ImageFile = Benzoyl-CoA.svg |
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| ImageFile = Benzoyl-CoA.svg |
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| IUPACName = |
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| IUPACName = |
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| OtherNames = benzoyl-S-CoA<br>S-Benzoate coenzyme A |
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| OtherNames = benzoyl-S-CoA<br>S-Benzoate coenzyme A |
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|Section1= {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| CASNo = 102185-37-5 |
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| CASNo = 102185-37-5 |
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| CASNo_Ref = |
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| CASNo_Ref = {{cascite|correct|??}} |
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| CASOther = |
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| CASNoOther = |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 6ZL6G9S5GY |
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| PubChem = 25245721 |
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| PubChem = 25245721 |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| SMILES = |
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| InChI = |
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| ChemSpiderID = 7822142 |
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| ChEBI = 15515 |
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| 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 |
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| 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 |
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| InChIKey = VEVJTUNLALKRNO-TYHXJLICBE |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| 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 |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = VEVJTUNLALKRNO-TYHXJLICSA-N |
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| MeSHName = |
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}} |
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|Section2= {{Chembox Properties |
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|Section2={{Chembox Properties |
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| 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> |
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| 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> |
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| MolarMass = 867.60 g/mol |
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| MolarMass = 867.60 g/mol |
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| ExactMass = 867.110123 u |
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| Appearance = |
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| Appearance = |
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| Density = |
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| Density = |
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| MeltingPt = <!-- °C --> |
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| MeltingPt = |
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| BoilingPt = <!-- °C --> |
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| BoilingPt = |
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| Solubility = |
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| Solubility = |
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}} |
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'''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, |
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'''Benzoyl-CoA''' is a molecule implied in the activity of the different enzymes ], ], ], ], ], ], ], ], ] and ]. |
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], ], ], ], ], ], and ] are suspected to be processed similarly.<ref name= Porter/> |
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==As substrate for reductases== |
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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>. |
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] |
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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. |
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==As a benzoyl donor== |
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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> |
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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> |
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==References== |
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==References== |
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{{reflist}} |
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{{reflist}} |
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] |
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] |
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{{metabolism-stub}} |
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