3-Phosphoglyceric acid Names Preferred IUPAC name (2R )-2-Hydroxy-3-(phosphonooxy)propanoic acid
Identifiers ChEBI ChEMBL ChemSpider DrugBank KEGG InChI=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
Y Key: OSJPPGNTCRNQQC-UWTATZPHSA-N
Y Properties C 3 H 7 O 7 P Molar mass 186.06 g/mol Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
3-Phosphoglyceric acid (3PG ,3-PGA , orPGA ) is theconjugate acid of3-phosphoglycerate orglycerate 3-phosphate (GP orG3P ).[ 1] biochemically significant metabolic intermediate in bothglycolysis and theCalvin-Benson cycle . The anion is often termed asPGA 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 CO2 fixation. Thus, two equivalents of 3-phosphoglycerate are produced for each molecule of CO2 that is fixed.[ 2] [ 3] [ 4] dephosphorylation (reduction ) of1,3-bisphosphoglycerate .[ 4] : 14
In the glycolytic pathway, 1,3-bisphosphoglycerate is dephosphorylated to form 3-phosphoglyceric acid in a coupled reaction producing twoATP viasubstrate-level phosphorylation .[ 5] [ 5] [ a] phosphoglycerate mutase , an enzyme that also catalyzes the reverse reaction.[ 6]
CompoundC00236 atKEGG Pathway Database. Enzyme2.7.2.3 atKEGG Pathway Database. CompoundC00197 atKEGG Pathway Database. Enzyme5.4.2.1 atKEGG Pathway Database. CompoundC00631 atKEGG Pathway Database.
Click on genes, proteins and metabolites below to link to respective articles. [ § 1]
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Glycolysis and Gluconeogenesis
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Calvin-Benson cycle [ edit ] In thelight-independent reactions (also known as the Calvin-Benson cycle), two 3-phosphoglycerate molecules are synthesized.RuBP , a 5-carbon sugar, undergoescarbon fixation , catalyzed by therubisco enzyme, to become an unstable 6-carbon intermediate. This intermediate is then cleaved into two, separate 3-carbon molecules of 3-PGA.[ 7] glyceraldehyde 3-phosphate (G3P) in two steps: thephosphorylation of 3-PGA into1,3-bisphosphoglyceric acid via the enzymephosphoglycerate kinase (the reverse of the reaction seen in glycolysis) and the subsequent catalysis byglyceraldehyde 3-phosphate dehydrogenase into G3P.[ 8] [ 9] [ 10] glucose orfructose or more complexstarches .[ 4] : 156 [ 8] [ 9]
Amino acid synthesis [ edit ] Glycerate 3-phosphate (formed from 3-phosphoglycerate) is also a precursor forserine , which, in turn, can createcysteine andglycine through thehomocysteine cycle.[ 11] [ 12] [ 13]
3-phosphoglycerate can be separated and measured usingpaper chromatography [ 14] column chromatography and other chromatographic separation methods.[ 15] gas-chromatography andliquid-chromatography mass spectrometry and has been optimized for evaluation usingtandem MS techniques.[ 1] [ 16] [ 17]
^a b "3-Phosphoglyceric acid (HMDB0000807)" .Human Metabolome Database . The Metabolomics Innovation Centre. Retrieved23 May 2021 .^ Berg, J.M.; Tymoczko, J.L.; Stryer, L. (2002).Biochemistry W.H. Freeman and Company .ISBN 0-7167-3051-0 ^ Nelson, D.L.; Cox, M.M. (2000).Lehninger, Principles of Biochemistry (3rd ed.). New York: Worth Publishing.ISBN 1-57259-153-6 ^a b c Leegood, R.C.; Sharkey, T.D.; von Caemmerer, S., eds. (2000).Photosynthesis: Physiology and Metabolism doi :10.1007/0-306-48137-5 .ISBN 978-0-7923-6143-5 S2CID 266763949 . ^a b Rye, Connie; Wise, Robert; Jurukovski, Vladimir; DeSaix, Jean; Choi, Jung; Avissar, Yael (2016)."Glycolysis" .Biology ^ 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 . ^ Andersson, I. (2008)."Catalysis and regulation in Rubisco" .Journal of Experimental Botany .59 (7):1555– 1568.doi :10.1093/jxb/ern091 PMID 18417482 . ^a b Moran, L. (2007)."The Calvin Cycle: Regeneration" .Sandwalk . Retrieved11 May 2021 . ^a b 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 . ^ 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 . ^ Igamberdiev, A.U.; Kleczkowski, L.A. (2018)."The Glycerate and Phosphorylated Pathways of Serine Synthesis in Plants: The Branches of Plant Glycolysis Linking Carbon and Nitrogen Metabolism" .Frontiers in Plant Science .9 (318): 318.doi :10.3389/fpls.2018.00318 PMC 5861185 PMID 29593770 . ^ Ichihara, A.; Greenberg, D.M. (1955)."Pathway of Serine Formation from Carbohydrate in Rat Liver" .PNAS .41 (9):605– 609.Bibcode :1955PNAS...41..605I .doi :10.1073/pnas.41.9.605 JSTOR 89140 .PMC 528146 PMID 16589713 . ^ 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 . ^ 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 PMID 13385236 . ^ Hofer, H.W. (1974). "Separation of glycolytic metabolites by column chromatography".Analytical Biochemistry .61 (1):54– 61.doi :10.1016/0003-2697(74)90332-7 .PMID 4278264 . ^ Shibayama, J.; Yuzyuk, T.N.; Cox, J.; et al. (2015)."Metabolic Remodeling in Moderate Synchronous versus Dyssynchronous Pacing-Induced Heart Failure: Integrated Metabolomics and Proteomics Study" .PLOS ONE .10 (3) e0118974.Bibcode :2015PLoSO..1018974S .doi :10.1371/journal.pone.0118974 PMC 4366225 PMID 25790351 . ^ Xu, J.; Zhai, Y.; Feng, L. (2019). "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 of Pharmaceutical and Biomedical Analysis .171 :171– 179.doi :10.1016/j.jpba.2019.04.022 .PMID 31005043 .S2CID 125170446 . ^ Note that 3-phosphoglycerate and 2-phosphoglycerate are isomers of one another
Receptor (ligands )
GlyR Tooltip Glycine receptor Positive modulators: Alcohols (e.g.,brometone ,chlorobutanol (chloretone) ,ethanol (alcohol) ,tert -butanol (2M2P)tribromoethanol ,trichloroethanol ,trifluoroethanol )Alkylbenzene sulfonate Anandamide Barbiturates (e.g.,pentobarbital ,sodium thiopental )Chlormethiazole D12-116 Dihydropyridines (e.g.,nicardipine )Etomidate Ginseng constituents (e.g.,ginsenosides (e.g.,ginsenoside-Rf ))Glutamic acid (glutamate) Ivermectin Ketamine Neuroactive steroids (e.g.,alfaxolone ,pregnenolone (eltanolone) ,pregnenolone acetate ,minaxolone ,ORG-20599 )Nitrous oxide Penicillin G Propofol Tamoxifen Tetrahydrocannabinol Triclofos Tropeines (e.g.,atropine ,bemesetron ,cocaine ,LY-278584 ,tropisetron ,zatosetron )Volatiles /gases (e.g.,chloral hydrate ,chloroform ,desflurane ,diethyl ether (ether) ,enflurane ,halothane ,isoflurane ,methoxyflurane ,sevoflurane ,toluene ,trichloroethane (methyl chloroform) ,trichloroethylene )Xenon Zinc Antagonists: 2-Aminostrychnine 2-Nitrostrychnine 4-Phenyl-4-formyl-N-methylpiperidine αEMBTL Bicuculline Brucine Cacotheline Caffeine Colchicine Colubrine Cyanotriphenylborate Dendrobine Diaboline Endocannabinoids (e.g.,2-AG ,anandamide (AEA) )Gaboxadol (THIP) Gelsemine iso-THAZ Isobutyric acid Isonipecotic acid Isostrychnine Laudanosine N-Methylbicuculline N-Methylstrychnine N,N-Dimethylmuscimol Nipecotic acid Pitrazepin Pseudostrychnine Quinolines (e.g.,4-hydroxyquinoline ,4-hydroxyquinoline-3-carboxylic acid ,5,7-CIQA ,7-CIQ ,7-TFQ ,7-TFQA )RU-5135 Sinomenine Strychnine THAZ Thiocolchicoside Tutin Negative modulators: Amiloride Benzodiazepines (e.g.,bromazepam ,clonazepam ,diazepam ,flunitrazepam ,flurazepam )Corymine Cyanotriphenylborate Daidzein Dihydropyridines (e.g.,nicardipine ,nifedipine ,nitrendipine )Furosemide Genistein Ginkgo constituents (e.g.,bilobalide ,ginkgolides (e.g.,ginkgolide A ,ginkgolide B ,ginkgolide C ,ginkgolide J ,ginkgolide M ))Imipramine NBQX Neuroactive steroids (e.g.,3α-androsterone sulfate ,3β-androsterone sulfate ,deoxycorticosterone ,DHEA sulfate ,pregnenolone sulfate ,progesterone )Opioids (e.g.,codeine ,dextromethorphan ,dextrorphan ,levomethadone ,levorphanol ,morphine ,oripavine ,pethidine ,thebaine )Picrotoxin (i.e.,picrotin andpicrotoxinin )PMBA Riluzole Tropeines (e.g.,bemesetron ,LY-278584 ,tropisetron ,zatosetron )Verapamil Zinc NMDAR Tooltip N-Methyl-D-aspartate receptor
Transporter (blockers )
GlyT1 Tooltip Glycine transporter 1 GlyT2 Tooltip Glycine transporter 2
