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{{Unreferenced stub|auto=yes|date=December 2009}} |
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{{Chembox |
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{{Chembox |
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| Verifiedfields = changed |
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| verifiedrevid = 386554704 |
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| ImageFile = Palmitoyl coenzyme A.svg |
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| ImageFile = Palmitoyl coenzyme A.svg |
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| ImageSize = 300px |
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| ImageSize = 300px |
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| IUPACName = 3′-''O''-Phosphonoadenosine 5′-<nowiki/>{(3''R'')-4-amino}-3-oxopropyl)amino]-3-hydroxy-2,2-dimethyl-4-oxobutyl dihydrogen diphosphate} |
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| IUPACName = |
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| SystematicName = ''O''<sup>1</sup>-<nowiki/>{methyl} ''O''<sup>3</sup>-<nowiki/>{(3''R'')-4-amino}-3-oxopropyl)amino]-3-hydroxy-2,2-dimethyl-4-oxobutyl} dihydrogen diphosphate |
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| OtherNames = |
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| OtherNames = |
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| Section1 = {{Chembox Identifiers |
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| Section1 = {{Chembox Identifiers |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 1763-10-6 |
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| PubChem = 986 |
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| CASNo = 1763-10-6 |
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| SMILES = |
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| PubChem = 644109 |
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| KEGG_Ref = {{keggcite|changed|kegg}} |
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| MeSHName = Palmitoyl+Coenzyme+A |
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| KEGG = C00154 |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID = 559149 |
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| SMILES = CCCCCCCCCCCCCCCC(=O)SCCNC(=O)CCNC(=O)(C(C)(C)COP(=O)(O)OP(=O)(O)OC1(((O1)n2cnc3c2ncnc3N)O)OP(=O)(O)O)O |
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| InChI = 1/C37H66N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-28(46)65-21-20-39-27(45)18-19-40-35(49)32(48)37(2,3)23-58-64(55,56)61-63(53,54)57-22-26-31(60-62(50,51)52)30(47)36(59-26)44-25-43-29-33(38)41-24-42-34(29)44/h24-26,30-32,36,47-48H,4-23H2,1-3H3,(H,39,45)(H,40,49)(H,53,54)(H,55,56)(H2,38,41,42)(H2,50,51,52)/t26-,30-,31-,32+,36-/m1/s1 |
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| InChIKey = MNBKLUUYKPBKDU-BBECNAHFBL |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChI = 1S/C37H66N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-28(46)65-21-20-39-27(45)18-19-40-35(49)32(48)37(2,3)23-58-64(55,56)61-63(53,54)57-22-26-31(60-62(50,51)52)30(47)36(59-26)44-25-43-29-33(38)41-24-42-34(29)44/h24-26,30-32,36,47-48H,4-23H2,1-3H3,(H,39,45)(H,40,49)(H,53,54)(H,55,56)(H2,38,41,42)(H2,50,51,52)/t26-,30-,31-,32+,36-/m1/s1 |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = MNBKLUUYKPBKDU-BBECNAHFSA-N |
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| MeSHName = Palmitoyl+Coenzyme+A |
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| Section2 = {{Chembox Properties |
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| Section2 = {{Chembox Properties |
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| C=37 | H=66 | N=7 | O=17 | P=3 | S=1 |
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| Formula = C<sub>37</sub>H<sub>66</sub>N<sub>7</sub>O<sub>17</sub>P<sub>3</sub>S |
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| Appearance = |
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| MolarMass = 1005.94 g/mol |
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| Section3 = {{Chembox Hazards |
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| Section3 = {{Chembox Hazards |
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'''Palmitoyl-CoA''' is an ] thioester. It is an "activated" form of ] and can be transported into the mitochondrial ] by the ] system (which transports fatty ] molecules into the ]), and once inside can participate in ]. Alternatively, palmitoyl-CoA is used as a substrate in the biosynthesis of ] (this biosynthetic pathway does not require transfer into the mitochondria).<ref>{{cite journal|author1=Brady, R.N.|author2=DiMari, S.J.|author3=Snell, E.E.|year=1969|title=Biosynthesis of sphingolipid bases. 3. Isolation and characterization of ketonic intermediates in the synthesis of sphingosine and dihydrosphingosine by cell-free extracts of ''Hansenula ciferri''|journal=J. Biol. Chem.|volume=244|issue=2|pages=491–496|doi=10.1016/S0021-9258(18)94455-8 |doi-access=free |pmid=4388074}}</ref><ref>{{cite journal|author1=Stoffel, W.|author2=Le Kim, D.|author3=Sticht, G.|year=1968|title=Biosynthesis of dihydrosphingosine in vitro|journal=Hoppe-Seyler's Z. Physiol. Chem.|volume=349|issue=5|pages=664–670|doi=10.1515/bchm2.1968.349.1.664|pmid=4386961}}</ref> |
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'''Palmitoyl CoA''' is an acyl-CoA thioester used in the biosynthesis of ]: |
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== Biosynthesis == |
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] |
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Palmitoyl CoA formed from palmitic acid, in the reaction below.<ref name=":0">{{Cite book|last1=Voet|first1=Donald|url=https://books.google.com/books?id=9T7hCgAAQBAJ&q=Fatty%20Acids%20Are%20Activated%20by%20Their%20Attachment%20to%20Coenzyme%20A%20voet%20fundamentals%20of%20biochemistry&pg=PA672|title=Fundamentals of Biochemistry: Life at the Molecular Level|last2=Voet|first2=Judith G.|last3=Pratt|first3=Charlotte W.|date=2016-02-29|publisher=John Wiley & Sons|isbn=978-1-118-91840-1|language=en}}</ref> |
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:{{Chem2 | Palmitate + CoA\-SH + ATP -> Palmitoyl\-CoA + AMP + Pyrophosphate }} |
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This reaction is often referred to as the "activation" of a fatty acid. The activation is catalyzed by ] and the reaction proceeds through a two step mechanism, in which palmitoyl-AMP is an intermediate.<ref>{{Cite journal|last1=Bar–Tana|first1=J.|last2=Rose|first2=G.|last3=Brandes|first3=R.|last4=Shapiro|first4=B.|date=1973-02-01|title=Palmitoyl-coenzyme A synthetase. Mechanism of reaction|journal=Biochemical Journal|volume=131|issue=2|pages=199–209|doi=10.1042/bj1310199|pmid=4722436|issn=0264-6021|pmc=1177459}}</ref> The reaction is driven to completion by the exergonic hydrolysis of pyrophosphate.<ref name=":0" /> |
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The activation of fatty acids occurs in the cytosol and beta-oxidation occurs in the mitochondria. However, long chain fatty acyl-CoA cannot cross the mitochondrial membrane. If palmitoyl-CoA is to enter the mitochondria, it must react with carnitine in order to be transported across: |
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:{{Chem2 | Palmitoyl\-CoA + Carnitine <-> Palmitoyl\-Carnitine + CoA\-SH }} |
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This transesterification reaction is catalyzed by ].<ref>{{Citation|last=Sharma|first=R.|chapter=Biochemical Mechanisms of Fatty Liver and Bioactive Foods|date=2013|title=Bioactive Food as Dietary Interventions for Liver and Gastrointestinal Disease|pages=709–741|publisher=Elsevier|doi=10.1016/b978-0-12-397154-8.00041-5|isbn=978-0-12-397154-8}}</ref> Palmitoyl-Carnitine may translocate across the membrane, and once on matrix side, the reaction proceeds in reverse as CoA-SH is recombined with palmitoyl-CoA, and released. Unattached carnitine is then shuttled back to the cytosolic side of mitochondrial membrane. |
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== Beta-oxidation == |
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Once inside the mitochondrial matrix, palmitoyl-CoA may undergo ]. The full oxidation of palmitic acid (or palmitoyl-CoA) results in 8 acetyl-CoA's, 7 ], 7 {{chem2|H+}}, and 7 ].<ref>{{Citation|last1=Kamel|first1=Kamel S.|title=Ketoacidosis|date=2017|work=Fluid, Electrolyte and Acid-Base Physiology|pages=99–139|publisher=Elsevier|isbn=978-0-323-35515-5|last2=Halperin|first2=Mitchell L.|doi=10.1016/b978-0-323-35515-5.00005-1}}</ref> The full reaction is below: |
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:{{Chem2 | Palmitoyl\-CoA + 7 CoA\-SH + 7 NAD+ + 7 FAD -> 8 Acetyl\-CoA + 7 NADH + 7 H+ + 7 FADH2 }} |
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== Sphingolipid biosynthesis == |
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Palmitoyl-CoA is also the starting substrate, along with serine, for sphingolipid biosynthesis. Palmitoyl CoA and serine participate in a condensation reaction catalyzed by ] (SPT), in which ] is formed. These reactions occur in the cytosol.<ref>{{Cite journal|last1=Michel|first1=Christoph|last2=van Echten-Deckert|first2=Gerhild|date=1997-10-20|title=Conversion of dihydroceramide to ceramide occurs at the cytosolic face of the endoplasmic reticulum|journal=FEBS Letters|volume=416|issue=2|pages=153–155|doi=10.1016/s0014-5793(97)01187-3|pmid=9369202|s2cid=467943|issn=0014-5793|doi-access=|bibcode=1997FEBSL.416..153M }}</ref> |
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==Additional images== |
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==See also== |
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{{DEFAULTSORT:Palmitoyl-Coa}} |
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* ] (CoA) |
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==References== |
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{{Reflist|2}} |
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{{Organic-compound-stub}} |
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{{Lysophospholipid signaling}} |
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{{DEFAULTSORT:Palmitoyl-Coa}} |
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