3-Phosphoglyceric acid
Names
Preferred IUPAC name
(2R )-2-Hydroxy-3-(phosphonooxy)propanoic acid
Identifiers
3DMet
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
C([C@H](C(=O)O)O)OP(=O)(O)O
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 , or PGA ) is the conjugate acid of 3-phosphoglycerate or glycerate 3-phosphate (GP or G3P ).
[1] This glycerate is a
biochemically significant metabolic intermediate in both
glycolysis and the
Calvin-Benson cycle . 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 CO2 fixation. Thus, two equivalents of 3-phosphoglycerate are produced for each molecule of CO2 that is fixed.
[2]
[3]
[4] In glycolysis, 3-phosphoglycerate is an intermediate following the
dephosphorylation (
reduction ) of
1,3-bisphosphoglycerate .
[4] : 14
Glycolysis
In the glycolytic pathway, 1,3-bisphosphoglycerate is dephosphorylated to form 3-phosphoglyceric acid in a coupled reaction producing two
ATP via
substrate-level phosphorylation .
[5] The single phosphate group left on the 3-PGA molecule then moves from an end carbon to a central carbon, producing 2-phosphoglycerate.
[5]
[a] This phosphate group relocation is catalyzed by
phosphoglycerate mutase , an enzyme that also catalyzes the reverse reaction.
[6]
Compound
C00236 at
KEGG Pathway Database. Enzyme
2.7.2.3 at
KEGG Pathway Database. Compound
C00197 at
KEGG Pathway Database. Enzyme
5.4.2.1 at
KEGG Pathway Database. Compound
C00631 at
KEGG Pathway Database.
Click on genes, proteins and metabolites below to link to respective articles.
[§ 1]
[[File:
|alt=Glycolysis and Gluconeogenesis
]]
Glycolysis and Gluconeogenesis
Calvin-Benson cycle
In the
light-independent reactions (also known as the Calvin-Benson cycle), two 3-phosphoglycerate molecules are synthesized.
RuBP , a 5-carbon sugar, undergoes
carbon fixation , catalyzed by the
rubisco enzyme, to become an unstable 6-carbon intermediate. This intermediate is then cleaved into two, separate 3-carbon molecules of 3-PGA.
[7] 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
glyceraldehyde 3-phosphate (G3P) in two steps: the
phosphorylation of 3-PGA into
1,3-bisphosphoglyceric acid via the enzyme
phosphoglycerate kinase (the reverse of the reaction seen in glycolysis) and the subsequent catalysis by
glyceraldehyde 3-phosphate dehydrogenase into G3P.
[8]
[10] G3P eventually reacts to form the sugars such as
glucose or
fructose or more complex
starches .
[4] : 156
[8]
Amino acid synthesis
Glycerate 3-phosphate (formed from 3-phosphoglycerate) is also a precursor for
serine , which, in turn, can create
cysteine and
glycine through the
homocysteine cycle.
[11]
[12]
[13]
Measurement
3-phosphoglycerate can be separated and measured using
paper chromatography
[14] as well as with
column chromatography and other chromatographic separation methods.
[15] It can be identified using both
gas-chromatography and
liquid-chromatography mass spectrometry and has been optimized for evaluation using
tandem MS techniques.
[1]
[16]
[17]
See also
References
^
a
b
"3-Phosphoglyceric acid (HMDB0000807)" . Human Metabolome Database . The Metabolomics Innovation Centre. Retrieved 23 May 2021 .
^ Berg, J.M.; Tymoczko, J.L.; Stryer, L. (2002).
Biochemistry (5th ed.). New York:
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 . Advances in Photosynthesis. Vol. 9. Kluwer Academic Publishers.
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 . OpenStax College.
^ 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 . Retrieved 11 May 2021 .
^ 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
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 and
picrotoxinin )
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