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3-Phosphoglyceric acid
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<h2 id="glycolysis">Glycolysis</h2> <p class="note">Main article: <a href="/facts/Glycolysis/a5ApxLoG">Glycolysis</a></p> <p>In the glycolytic pathway, 1,3-bisphosphoglycerate is dephosphorylated to form 3-phosphoglyceric acid in a coupled reaction producing two <a href="/facts/Adenosine_triphosphate/nB9bwgcU">ATP</a> via <a href="/facts/Substrate-level_phosphorylation/1hxqqgBS">substrate-level phosphorylation</a>.<a class="footnote-ref" id="fnref:6" href="#fn:6"><sup>6</sup></a> The single phosphate group left on the 3-PGA molecule then moves from an end carbon to a central carbon, producing 2-phosphoglycerate.<a class="footnote-ref" id="fnref:7" href="#fn:7"><sup>7</sup></a><a class="footnote-ref" id="fnref:8" href="#fn:8"><sup>8</sup></a> This phosphate group relocation is catalyzed by <a href="/facts/Phosphoglycerate_mutase/sz0JH3dk">phosphoglycerate mutase</a>, an enzyme that also catalyzes the reverse reaction.<a class="footnote-ref" id="fnref:9" href="#fn:9"><sup>9</sup></a> </p> <table><tbody><tr><td><a href="/facts/1,3-bisphosphoglycerate/aL6aR6ha">1,3-bisphospho-D-glycerate</a></td><td colspan="2"><a href="/facts/3-phosphoglycerate_kinase/BpUE8QNw">3-phosphoglycerate kinase</a></td><td><a href="/facts/3-phosphoglycerate/vI3TSY4D">3-phospho-D-glycerate</a></td><td colspan="2"><a href="/facts/Phosphoglyceromutase/sz0JH3dk">Phosphoglyceromutase</a></td><td><a href="/facts/2-phosphoglycerate/3xYk095o">2-phospho-D-glycerate</a></td></tr><tr><td rowspan="5"></td><td colspan="2"> </td><td rowspan="5"></td><td colspan="2"> </td><td rowspan="5"></td></tr><tr><td><a href="/facts/Adenosine_diphosphate/JEDnsCjn">ADP</a></td><td><a href="/facts/Adenosine_triphosphate/nB9bwgcU">ATP</a></td><td></td><td></td></tr><tr><td colspan="2"></td><td colspan="2"></td></tr><tr><td><a href="/facts/Adenosine_diphosphate/JEDnsCjn">ADP</a></td><td><a href="/facts/Adenosine_triphosphate/nB9bwgcU">ATP</a></td><td></td><td></td></tr><tr><td colspan="2"> </td><td colspan="2"> </td></tr><tr><td> </td><td colspan="2"><a href="/facts/3-phosphoglycerate_kinase/BpUE8QNw">3-phosphoglycerate kinase</a></td><td> </td><td colspan="2"><a href="/facts/Phosphoglyceromutase/sz0JH3dk">Phosphoglyceromutase</a></td><td></td></tr></tbody></table> <p>Compound <a href="http://www.genome.jp/dbget-bin/www_bget?compound+C00236">C00236</a> at <a href="/facts/KEGG/pK5La8ad">KEGG</a> Pathway Database. Enzyme <a href="http://www.genome.jp/dbget-bin/www_bget?enzyme+2.7.2.3">2.7.2.3</a> at <a href="/facts/KEGG/pK5La8ad">KEGG</a> Pathway Database. Compound <a href="http://www.genome.jp/dbget-bin/www_bget?compound+C00197">C00197</a> at <a href="/facts/KEGG/pK5La8ad">KEGG</a> Pathway Database. Enzyme <a href="http://www.genome.jp/dbget-bin/www_bget?enzyme+5.4.2.1">5.4.2.1</a> at <a href="/facts/KEGG/pK5La8ad">KEGG</a> Pathway Database. Compound <a href="http://www.genome.jp/dbget-bin/www_bget?compound+C00631">C00631</a> at <a href="/facts/KEGG/pK5La8ad">KEGG</a> Pathway Database. </p><p><i>Click on genes, proteins and metabolites below to link to respective articles.</i><a class="footnote-ref" id="fnref:10" href="#fn:10"><sup>10</sup></a> </p> <h2 id="calvin-benson-cycle">Calvin-Benson cycle</h2> <p>In the <a href="/facts/Light-independent_reactions/M1bIgQb9">light-independent reactions</a> (also known as the Calvin-Benson cycle), two 3-phosphoglycerate molecules are synthesized. <a href="/facts/Ribulose-1,5-bisphosphate/1DwB2uHE">RuBP</a>, a 5-carbon sugar, undergoes <a href="/facts/Carbon_fixation/JqvfmCdH">carbon fixation</a>, catalyzed by the <a href="/facts/Rubisco/C8asuQsc">rubisco</a> enzyme, to become an unstable 6-carbon intermediate. This intermediate is then cleaved into two, separate 3-carbon molecules of 3-PGA.<a class="footnote-ref" id="fnref:11" href="#fn:11"><sup>11</sup></a> 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 <a href="/facts/Glyceraldehyde_3-phosphate/Wy3FMLzJ">glyceraldehyde 3-phosphate</a> (G3P) in two steps: the <a href="/facts/Phosphorylation/LXUEEeIL">phosphorylation</a> of 3-PGA into <a href="/facts/1,3-bisphosphoglyceric_acid/aL6aR6ha">1,3-bisphosphoglyceric acid</a> via the enzyme <a href="/facts/Phosphoglycerate_kinase/BpUE8QNw">phosphoglycerate kinase</a> (the reverse of the reaction seen in glycolysis) and the subsequent catalysis by <a href="/facts/Glyceraldehyde_3-phosphate_dehydrogenase/lkfwRuDx">glyceraldehyde 3-phosphate dehydrogenase</a> into G3P.<a class="footnote-ref" id="fnref:12" href="#fn:12"><sup>12</sup></a><a class="footnote-ref" id="fnref:13" href="#fn:13"><sup>13</sup></a><a class="footnote-ref" id="fnref:14" href="#fn:14"><sup>14</sup></a> G3P eventually reacts to form the sugars such as <a href="/facts/Glucose/oUSkoLCD">glucose</a> or <a href="/facts/Fructose/pEqWJC2N">fructose</a> or more complex <a href="/facts/Starch/gHAqGfJb">starches</a>.<a class="footnote-ref" id="fnref:15" href="#fn:15"><sup>15</sup></a>: 156 <a class="footnote-ref" id="fnref:16" href="#fn:16"><sup>16</sup></a><a class="footnote-ref" id="fnref:17" href="#fn:17"><sup>17</sup></a> </p> <h2 id="amino-acid-synthesis">Amino acid synthesis</h2> <p>Glycerate 3-phosphate (formed from 3-phosphoglycerate) is also a precursor for <a href="/facts/Serine/4duVl30B">serine</a>, which, in turn, can create <a href="/facts/Cysteine/kbqvUm6d">cysteine</a> and <a href="/facts/Glycine/3nXI1hqW">glycine</a> through the <a href="/facts/Homocysteine/m4cgrRBG">homocysteine</a> cycle.<a class="footnote-ref" id="fnref:18" href="#fn:18"><sup>18</sup></a><a class="footnote-ref" id="fnref:19" href="#fn:19"><sup>19</sup></a><a class="footnote-ref" id="fnref:20" href="#fn:20"><sup>20</sup></a> </p> <h2 id="measurement">Measurement</h2> <p>3-phosphoglycerate can be separated and measured using <a href="/facts/Paper_chromatography/1qDcbIp0">paper chromatography</a><a class="footnote-ref" id="fnref:21" href="#fn:21"><sup>21</sup></a> as well as with <a href="/facts/Column_chromatography/fPNBKwx8">column chromatography</a> and other chromatographic separation methods.<a class="footnote-ref" id="fnref:22" href="#fn:22"><sup>22</sup></a> It can be identified using both <a href="/facts/Gas_chromatography%E2%80%93mass_spectrometry/Gm3eCCoQ">gas-chromatography</a> and <a href="/facts/Liquid_chromatography%E2%80%93mass_spectrometry/nGlDC6Hw">liquid-chromatography mass spectrometry</a> and has been optimized for evaluation using <a href="/facts/Tandem_mass_spectrometry/otT5Q9tY">tandem MS</a> techniques.<a class="footnote-ref" id="fnref:23" href="#fn:23"><sup>23</sup></a><a class="footnote-ref" id="fnref:24" href="#fn:24"><sup>24</sup></a><a class="footnote-ref" id="fnref:25" href="#fn:25"><sup>25</sup></a> </p> <h2 id="see-also">See also</h2> <ul><li><a href="/facts/2-Phosphoglyceric_acid/3xYk095o">2-Phosphoglyceric acid</a></li> <li><a href="/facts/Calvin-Benson_cycle/M1bIgQb9">Calvin-Benson cycle</a></li> <li><a href="/facts/Photosynthesis/TMV7w693">Photosynthesis</a></li> <li><a href="/facts/Ribulose_1,5-bisphosphate/1DwB2uHE">Ribulose 1,5-bisphosphate</a></li></ul> <h2 id="references">References</h2> <ol> <li id="fn:1"><p>"3-Phosphoglyceric acid (HMDB0000807)". Human Metabolome Database. The Metabolomics Innovation Centre. Retrieved 23 May 2021. <a href="https://hmdb.ca/metabolites/HMDB0000807" target="_blank">https://hmdb.ca/metabolites/HMDB0000807</a> <a href="#fnref:1" class="footnote-back-ref">↩</a></p></li> <li id="fn:2"><p>Berg, J.M.; Tymoczko, J.L.; Stryer, L. (2002). Biochemistry (5th ed.). New York: W.H. Freeman and Company. ISBN 0-7167-3051-0. <a href="0-7167-3051-0" target="_blank">0-7167-3051-0</a> <a href="#fnref:2" class="footnote-back-ref">↩</a></p></li> <li id="fn:3"><p>Nelson, D.L.; Cox, M.M. (2000). Lehninger, Principles of Biochemistry (3rd ed.). New York: Worth Publishing. ISBN 1-57259-153-6. <a href="1-57259-153-6" target="_blank">1-57259-153-6</a> <a href="#fnref:3" class="footnote-back-ref">↩</a></p></li> <li id="fn:4"><p>Leegood, R.C.; Sharkey, T.D.; von Caemmerer, S., eds. (2000). Photosynthesis: Physiology and Metabolism. Advances in Photosynthesis. Vol. 9. Kluwer Academic Publishers. doi:10.1007/0-306-48137-5. ISBN 978-0-7923-6143-5. S2CID 266763949. <a href="978-0-7923-6143-5" target="_blank">978-0-7923-6143-5</a> <a href="#fnref:4" class="footnote-back-ref">↩</a></p></li> <li id="fn:5"><p>Leegood, R.C.; Sharkey, T.D.; von Caemmerer, S., eds. (2000). Photosynthesis: Physiology and Metabolism. Advances in Photosynthesis. Vol. 9. Kluwer Academic Publishers. doi:10.1007/0-306-48137-5. ISBN 978-0-7923-6143-5. S2CID 266763949. <a href="978-0-7923-6143-5" target="_blank">978-0-7923-6143-5</a> <a href="#fnref:5" class="footnote-back-ref">↩</a></p></li> <li id="fn:6"><p>Rye, Connie; Wise, Robert; Jurukovski, Vladimir; DeSaix, Jean; Choi, Jung; Avissar, Yael (2016). "Glycolysis". Biology. OpenStax College. <a href="https://openstax.org/books/biology/pages/7-2-glycolysis" target="_blank">https://openstax.org/books/biology/pages/7-2-glycolysis</a> <a href="#fnref:6" class="footnote-back-ref">↩</a></p></li> <li id="fn:7"><p>Rye, Connie; Wise, Robert; Jurukovski, Vladimir; DeSaix, Jean; Choi, Jung; Avissar, Yael (2016). "Glycolysis". Biology. OpenStax College. <a href="https://openstax.org/books/biology/pages/7-2-glycolysis" target="_blank">https://openstax.org/books/biology/pages/7-2-glycolysis</a> <a href="#fnref:7" class="footnote-back-ref">↩</a></p></li> <li id="fn:8"><p>Note that 3-phosphoglycerate and 2-phosphoglycerate are isomers of one another <a href="#fnref:8" class="footnote-back-ref">↩</a></p></li> <li id="fn:9"><p>Rose, Z.B.; Dube, S. (1976). "Rates of phosphorylation and dephosphorylation of phosphoglycerate mutase and bisphosphoglycerate synthase". Journal of Biological Chemistry. 251 (16): 4817–4822. doi:10.1016/S0021-9258(17)33188-5. PMID 8447. <a href="https://doi.org/10.1016%2FS0021-9258%2817%2933188-5" target="_blank">https://doi.org/10.1016%2FS0021-9258%2817%2933188-5</a> <a href="#fnref:9" class="footnote-back-ref">↩</a></p></li> <li id="fn:10"><p>The interactive pathway map can be edited at WikiPathways: "GlycolysisGluconeogenesis_WP534". <a href="http://www.wikipathways.org/index.php/Pathway:WP534" target="_blank">http://www.wikipathways.org/index.php/Pathway:WP534</a> <a href="#fnref:10" class="footnote-back-ref">↩</a></p></li> <li id="fn:11"><p>Andersson, I. (2008). "Catalysis and regulation in Rubisco". Journal of Experimental Botany. 59 (7): 1555–1568. doi:10.1093/jxb/ern091. PMID 18417482. <a href="https://doi.org/10.1093%2Fjxb%2Fern091" target="_blank">https://doi.org/10.1093%2Fjxb%2Fern091</a> <a href="#fnref:11" class="footnote-back-ref">↩</a></p></li> <li id="fn:12"><p>Moran, L. (2007). "The Calvin Cycle: Regeneration". Sandwalk. Retrieved 11 May 2021. <a href="https://sandwalk.blogspot.com/2007/07/calvin-cycle-regeneration.html" target="_blank">https://sandwalk.blogspot.com/2007/07/calvin-cycle-regeneration.html</a> <a href="#fnref:12" class="footnote-back-ref">↩</a></p></li> <li id="fn:13"><p>Pettersson, G.; Ryde-Pettersson, Ulf (1988). "A mathematical model of the Calvin photosynthesis cycle". European Journal of Biochemistry. 175 (3): 661–672. doi:10.1111/j.1432-1033.1988.tb14242.x. PMID 3137030. <a href="https://lup.lub.lu.se/record/2ee3ec8e-69e9-4250-a6cc-fb016bf097a0" target="_blank">https://lup.lub.lu.se/record/2ee3ec8e-69e9-4250-a6cc-fb016bf097a0</a> <a href="#fnref:13" class="footnote-back-ref">↩</a></p></li> <li id="fn:14"><p>Fridlyand, L.E.; Scheibe, R. (1999). "Regulation of the Calvin cycle for CO2 fixation as an example for general control mechanisms in metabolic cycles". Biosystems. 51 (2): 79–93. doi:10.1016/S0303-2647(99)00017-9. PMID 10482420. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:14" class="footnote-back-ref">↩</a></p></li> <li id="fn:15"><p>Leegood, R.C.; Sharkey, T.D.; von Caemmerer, S., eds. (2000). Photosynthesis: Physiology and Metabolism. Advances in Photosynthesis. Vol. 9. Kluwer Academic Publishers. doi:10.1007/0-306-48137-5. ISBN 978-0-7923-6143-5. S2CID 266763949. <a href="978-0-7923-6143-5" target="_blank">978-0-7923-6143-5</a> <a href="#fnref:15" class="footnote-back-ref">↩</a></p></li> <li id="fn:16"><p>Moran, L. (2007). "The Calvin Cycle: Regeneration". Sandwalk. Retrieved 11 May 2021. <a href="https://sandwalk.blogspot.com/2007/07/calvin-cycle-regeneration.html" target="_blank">https://sandwalk.blogspot.com/2007/07/calvin-cycle-regeneration.html</a> <a href="#fnref:16" class="footnote-back-ref">↩</a></p></li> <li id="fn:17"><p>Pettersson, G.; Ryde-Pettersson, Ulf (1988). "A mathematical model of the Calvin photosynthesis cycle". 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Bibcode:1955PNAS...41..605I. doi:10.1073/pnas.41.9.605. JSTOR 89140. PMC 528146. PMID 16589713. <a href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC528146" target="_blank">https://www.ncbi.nlm.nih.gov/pmc/articles/PMC528146</a> <a href="#fnref:19" class="footnote-back-ref">↩</a></p></li> <li id="fn:20"><p>Hanford, J.; Davies, D.D. (1958). "Formation of Phosphoserine from 3-Phosphoglycerate in Higher Plants". Nature. 182 (4634): 532–533. Bibcode:1958Natur.182..532H. doi:10.1038/182532a0. S2CID 4192791. <a href="/wiki/Bibcode_(identifier)" target="_blank">/wiki/Bibcode_(identifier)</a> <a href="#fnref:20" class="footnote-back-ref">↩</a></p></li> <li id="fn:21"><p>Cowgill, R.W.; Pizer, L.I. (1956). "Purification and Some Properties of Phosphorylglyceric Acid Mutase from Rabbit Skeletal Muscle". Journal of Biological Chemistry. 223 (2): 885–895. doi:10.1016/S0021-9258(18)65087-2. 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