| Revision as of 18:01, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 472757437 of page 3-Phosphoglyceric_acid for the Chem/Drugbox validation project (updated: 'CASNo'). |
Latest revision as of 06:26, 2 January 2025 edit Arthurfragoso (talk | contribs)Extended confirmed users2,080 edits Fixes image in dark mode |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{Chembox |
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{{Chembox |
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| Verifiedfields = changed |
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|Verifiedfields = changed |
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| verifiedrevid = 456501818 |
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|verifiedrevid = 477220162 |
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| ImageFile = Glycerate 3-phosphate.svg |
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|ImageFile = D-3-Phosphoglycerinsäure.svg |
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|ImageClass = skin-invert |
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| ImageName = Skeletal formula |
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|ImageSize = 200px |
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| ImageFile1 = 3-Phospho-D-glyceric-acid-3D-balls.png |
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| ImageName1 = Ball-and-stick model |
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|ImageName1 = Ball-and-stick model |
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|ImageAlt = Skeletal structure of 3-Phosphoglyceric acid |
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| IUPACName = (2''R'')-2-Hydroxy-3-phosphonooxypropanoic acid |
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|PIN = (2''R'')-2-Hydroxy-3-(phosphonooxy)propanoic acid |
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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|changed|??}} |
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|CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = <!-- blanked - oldvalue: 820-11-1 --> |
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|CASNo = 820-11-1 |
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| PubChem = 439183 |
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|PubChem = 439183 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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|ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 1160563 |
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|ChEMBL = 1160563 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 388326 |
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|ChemSpiderID = 388326 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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|ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 17794 |
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|ChEBI = 17794 |
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|DrugBank = DB04510 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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|KEGG = C00197 |
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| StdInChI = 1S/C3H7O7P/c4-2(3(5)6)1-10-11(7,8)9/h2,4H,1H2,(H,5,6)(H2,7,8,9)/t2-/m1/s1 |
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|3DMet = C00197 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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|StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = OSJPPGNTCRNQQC-UWTATZPHSA-N |
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|StdInChI = 1S/C3H7O7P/c4-2(3(5)6)1-10-11(7,8)9/h2,4H,1H2,(H,5,6)(H2,7,8,9)/t2-/m1/s1 |
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| SMILES = C((C(=O)O)O)OP(=O)(O)O |
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|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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|StdInChIKey = OSJPPGNTCRNQQC-UWTATZPHSA-N |
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|SMILES = C((C(=O)O)O)OP(=O)(O)O |
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}} |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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|C=3 | H=7 | O=7 | P=1 |
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| Formula = |
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|MolarMass = 186.06 g/mol |
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| C = 3 | H = 7 | O = 7 | P = 1 |
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| MolarMass = 186.06 g/mol |
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| Appearance = |
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| Section3 = {{Chembox Hazards |
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| MainHazards = |
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| FlashPt = |
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}} |
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'''3-Phosphoglyceric acid''' ('''3PG''', '''3-PGA''', or '''PGA''') is the conjugate acid of '''3-phosphoglycerate''' or '''glycerate 3-phosphate''' ('''GP''' or '''G3P''').<ref name="hmdb">{{cite web | website = Human Metabolome Database | title = 3-Phosphoglyceric acid (HMDB0000807) | publisher = The Metabolomics Innovation Centre | url = https://hmdb.ca/metabolites/HMDB0000807 | access-date = 23 May 2021}}</ref> This glycerate is a ] significant metabolic intermediate in both ] and the ]. The anion is often termed as '''PGA''' when referring to the Calvin-Benson cycle. In the Calvin-Benson cycle, 3-phosphoglycerate is typically the product of the spontaneous scission of an unstable 6-carbon intermediate formed upon CO<sub>2</sub> fixation. Thus, two equivalents of 3-phosphoglycerate are produced for each molecule of CO<sub>2</sub> that is fixed.<ref>{{cite book |last1=Berg |first1=J.M. |last2=Tymoczko | first2 = J.L. | last3 = Stryer | first3 = L. |title=Biochemistry |year=2002 |edition=5th |publisher=] |location=New York |isbn=0-7167-3051-0 |url=https://archive.org/details/biochemistrychap00jere |url-access=registration }}</ref><ref name="lehninger2000">{{cite book | last1 = Nelson | first1 = D.L. | last2 = Cox | first2 = M.M. | title = Lehninger, Principles of Biochemistry | edition = 3rd | publisher = Worth Publishing | location = New York | date = 2000 | isbn = 1-57259-153-6}}</ref><ref name="ppm">{{cite book | title = Photosynthesis: Physiology and Metabolism | editor1-last = Leegood | editor1-first = R.C. | editor2-last = Sharkey | editor2-first = T.D. | editor3-last = von Caemmerer | editor3-first = S. | date = 2000 | publisher = Kluwer Academic Publishers | series = Advances in Photosynthesis | volume = 9 | isbn = 978-0-7923-6143-5 | doi = 10.1007/0-306-48137-5 | s2cid = 266763949 | url = https://archive.org/details/springer_10.1007-0-306-48137-5/}}</ref> In glycolysis, 3-phosphoglycerate is an intermediate following the ] (]) of ].<ref name="ppm" />{{rp|14}} |
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==Glycolysis== |
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{{main|Glycolysis}} |
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In the glycolytic pathway, 1,3-bisphosphoglycerate is dephosphorylated to form 3-phosphoglyceric acid in a coupled reaction producing two ] via ].<ref name="openstaxbio">{{cite book | first1 = Connie | last1 = Rye | first2 = Robert | last2 = Wise | first3 = Vladimir | last3 = Jurukovski | first4 = Jean | last4 = DeSaix | first5 = Jung | last5 = Choi | first6 = Yael | last6 = Avissar | title = Biology | publisher = OpenStax College | chapter = Glycolysis | chapter-url = https://openstax.org/books/biology/pages/7-2-glycolysis | url = https://openstax.org/books/biology/pages/1-introduction | date = 2016}}</ref> The single phosphate group left on the 3-PGA molecule then moves from an end carbon to a central carbon, producing 2-phosphoglycerate.<ref name="openstaxbio" />{{efn|Note that 3-phosphoglycerate and 2-phosphoglycerate are isomers of one another}} This phosphate group relocation is catalyzed by ], an enzyme that also catalyzes the reverse reaction.<ref name="rose1976">{{cite journal | title = Rates of phosphorylation and dephosphorylation of phosphoglycerate mutase and bisphosphoglycerate synthase | last1 = Rose | first1 = Z.B. | last2 = Dube | first2 = S. | journal = Journal of Biological Chemistry | date = 1976 | volume = 251 | issue = 16 | pages = 4817–4822 | doi = 10.1016/S0021-9258(17)33188-5 | pmid = 8447| doi-access = free }}</ref> |
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</div> |
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{{KEGG compound|C00236}} {{KEGG enzyme|2.7.2.3}} {{KEGG compound|C00197}} {{KEGG enzyme|5.4.2.1}} {{KEGG compound|C00631}} |
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{{GlycolysisGluconeogenesis_WP534|highlight=3-Phosphoglyceric_acid}} |
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==Calvin-Benson cycle== |
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In the ] (also known as the Calvin-Benson cycle), two 3-phosphoglycerate molecules are synthesized. ], a 5-carbon sugar, undergoes ], catalyzed by the ] enzyme, to become an unstable 6-carbon intermediate. This intermediate is then cleaved into two, separate 3-carbon molecules of 3-PGA.<ref name="andersson2008">{{cite journal | last = Andersson | first = I. | title = Catalysis and regulation in Rubisco | journal = Journal of Experimental Botany | volume = 59 | issue = 7 | date = 2008 | pages = 1555–1568 | doi = 10.1093/jxb/ern091 | pmid = 18417482| doi-access = free }}</ref> One of the resultant 3-PGA molecules continues through the Calvin-Benson cycle to be regenerated into RuBP while the other is reduced to form one molecule of ] (G3P) in two steps: the ] of 3-PGA into ] via the enzyme ] (the reverse of the reaction seen in glycolysis) and the subsequent catalysis by ] into G3P.<ref name="moran2007">{{cite web | last = Moran | first = L. | date = 2007 | url = https://sandwalk.blogspot.com/2007/07/calvin-cycle-regeneration.html | title = The Calvin Cycle: Regeneration | website = Sandwalk | access-date = 11 May 2021}}</ref><ref name="pettersson1988">{{cite journal | last1 = Pettersson | first1 = G. | last2 = Ryde-Pettersson | first2 = Ulf | title = A mathematical model of the Calvin photosynthesis cycle | journal = European Journal of Biochemistry | volume = 175 | issue = 3 | pages = 661–672 | date = 1988 | doi = 10.1111/j.1432-1033.1988.tb14242.x | pmid = 3137030| url = https://lup.lub.lu.se/record/2ee3ec8e-69e9-4250-a6cc-fb016bf097a0 | doi-access = free }}</ref><ref name="fridlyand1999">{{cite journal | title = Regulation of the Calvin cycle for CO2 fixation as an example for general control mechanisms in metabolic cycles | last1 = Fridlyand | first1 = L.E. | last2 = Scheibe | first2 = R. | journal = Biosystems | volume = 51 | issue = 2 | date = 1999 | pages = 79–93 | doi = 10.1016/S0303-2647(99)00017-9 | pmid = 10482420}}</ref> G3P eventually reacts to form the sugars such as ] or ] or more complex ]es.<ref name="ppm" />{{rp|156}}<ref name="moran2007" /><ref name="pettersson1988" /> |
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==Amino acid synthesis== |
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Glycerate 3-phosphate (formed from 3-phosphoglycerate) is also a precursor for ], which, in turn, can create ] and ] through the ] cycle.<ref name="Igamberdiev2018">{{cite journal | last1 = Igamberdiev | first1 = A.U. | last2 = Kleczkowski | first2 = L.A. | title = The Glycerate and Phosphorylated Pathways of Serine Synthesis in Plants: The Branches of Plant Glycolysis Linking Carbon and Nitrogen Metabolism | journal = Frontiers in Plant Science | volume = 9 | issue = 318 | doi = 10.3389/fpls.2018.00318 | date = 2018 | page = 318 | pmid = 29593770| pmc = 5861185 | doi-access = free }}</ref><ref name="ichihara1955">{{cite journal | last1 = Ichihara | first1 = A. | last2 = Greenberg | first2 = D.M. | title = Pathway of Serine Formation from Carbohydrate in Rat Liver | journal = PNAS | date = 1955 | volume = 41 | number = 9 | pages = 605–609 | doi = 10.1073/pnas.41.9.605 | jstor = 89140 | pmid = 16589713| pmc = 528146 | bibcode = 1955PNAS...41..605I | doi-access = free}}</ref><ref name="hanford1958">{{cite journal | title = Formation of Phosphoserine from 3-Phosphoglycerate in Higher Plants | last1 = Hanford | first1 = J. | last2 = Davies | first2 = D.D. | journal = Nature | date = 1958 | volume = 182 | issue = 4634 | pages = 532–533 | doi = 10.1038/182532a0| bibcode = 1958Natur.182..532H | s2cid = 4192791 }}</ref> |
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==Measurement== |
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3-phosphoglycerate can be separated and measured using ]<ref name="cowgill1956">{{cite journal | last1 = Cowgill | first1 = R.W. | last2 = Pizer | first2 = L.I. | title = Purification and Some Properties of Phosphorylglyceric Acid Mutase from Rabbit Skeletal Muscle | journal = Journal of Biological Chemistry | volume = 223 | issue = 2 | date = 1956 | pages = 885–895 | doi = 10.1016/S0021-9258(18)65087-2 | pmid = 13385236| doi-access = free}}</ref> as well as with ] and other chromatographic separation methods.<ref name="hofer1974">{{cite journal | last1 = Hofer | first1 = H.W. | title = Separation of glycolytic metabolites by column chromatography | journal = Analytical Biochemistry | date = 1974 | volume = 61 | issue = 1 | pages = 54–61 | doi = 10.1016/0003-2697(74)90332-7 | pmid = 4278264}}</ref> It can be identified using both ] and ] and has been optimized for evaluation using ] techniques.<ref name="hmdb" /><ref name="sibayama2015">{{cite journal | last1 = Shibayama | first1 = J. | last2 = Yuzyuk | first2 = T.N. | last3 = Cox | first3 = J. | display-authors = etal | title = Metabolic Remodeling in Moderate Synchronous versus Dyssynchronous Pacing-Induced Heart Failure: Integrated Metabolomics and Proteomics Study | journal = PLOS ONE | date = 2015 | volume = 10 | issue = 3 | pages = e0118974 | doi = 10.1371/journal.pone.0118974 | pmid = 25790351| pmc = 4366225 | bibcode = 2015PLoSO..1018974S | doi-access = free }}</ref><ref name="xu2019">{{cite journal | last1 = Xu | first1 = J. | last2 = Zhai | first2 = Y. | last3 = Feng | first3 = L. | title = An optimized analytical method for cellular targeted quantification of primary metabolites in tricarboxylic acid cycle and glycolysis using gas chromatography-tandem mass spectrometry and its application in three kinds of hepatic cell lines | journal = Journal of Pharmaceutical and Biomedical Analysis | volume = 171 | date = 2019 | pages = 171–179 | doi = 10.1016/j.jpba.2019.04.022| pmid = 31005043 | s2cid = 125170446}}</ref> |
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==See also== |
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* ] |
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* ] |
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* ] |
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* ] |
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==References== |
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{{Reflist}} |
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{{notelist}} |
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{{Glycolysis}} |
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{{Amino acid metabolism intermediates}} |
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{{Glycinergics}} |
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{{DEFAULTSORT:Phosphoglyceric Acid, 3-}} |
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] |
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