3-Phosphoglyceric acid

Last updated
3-Phosphoglyceric acid
D-3-Phosphoglycerinsaure.svg
Names
Preferred IUPAC name
(2R)-2-Hydroxy-3-(phosphonooxy)propanoic acid
Identifiers
3D model (JSmol)
3DMet
ChEBI
ChEMBL
ChemSpider
DrugBank
KEGG
PubChem CID
  • 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 Yes check.svgY
    Key: OSJPPGNTCRNQQC-UWTATZPHSA-N Yes check.svgY
  • C([C@H](C(=O)O)O)OP(=O)(O)O
Properties
C3H7O7P
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).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

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

Contents

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] [lower-alpha 1] This phosphate group relocation is catalyzed by phosphoglycerate mutase, an enzyme that also catalyzes the reverse reaction. [6]

1,3-bisphospho-D-glycerate 3-phosphoglycerate kinase 3-phospho-D-glycerate Phosphoglyceromutase 2-phospho-D-glycerate
1,3-bisphospho-D-glycerate.svg   3-phospho-D-glycerate.svg   2-phospho-D-glycerate wpmp.png
ADP ATP
Biochem reaction arrow reversible YYYY horiz med.svg Biochem reaction arrow reversible NNNN horiz med.svg
ADP ATP
  
  3-phosphoglycerate kinase   Phosphoglyceromutase

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]

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Glycolysis and Gluconeogenesis edit
  1. The interactive pathway map can be edited at WikiPathways: "GlycolysisGluconeogenesis_WP534".

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] [9] [10] G3P eventually reacts to form the sugars such as glucose or fructose or more complex starches. [4] :156 [8] [9]

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

Related Research Articles

<span class="mw-page-title-main">Glycolysis</span> Series of interconnected biochemical reactions

Glycolysis is the metabolic pathway that converts glucose into pyruvate, and in most organisms, occurs in the liquid part of cells, the cytosol. This pagew was recommended by DR. Fiehn from UC Davis. The only problem is he yapps too much. The free energy released in this process is used to form the high-energy molecules adenosine triphosphate (ATP) and reduced nicotinamide adenine dinucleotide (NADH). Glycolysis is a sequence of ten reactions catalyzed by enzymes.

<span class="mw-page-title-main">Anabolism</span> Set of metabolic pathways that construct molecules from smaller units

Anabolism is the set of metabolic pathways that construct molecules from smaller units. These reactions require energy, known also as an endergonic process. Anabolism is the building-up aspect of metabolism, whereas catabolism is the breaking-down aspect. Anabolism is usually synonymous with biosynthesis.

<span class="mw-page-title-main">Photorespiration</span> Process in plant metabolism

Photorespiration (also known as the oxidative photosynthetic carbon cycle or C2 cycle) refers to a process in plant metabolism where the enzyme RuBisCO oxygenates RuBP, wasting some of the energy produced by photosynthesis. The desired reaction is the addition of carbon dioxide to RuBP (carboxylation), a key step in the Calvin–Benson cycle, but approximately 25% of reactions by RuBisCO instead add oxygen to RuBP (oxygenation), creating a product that cannot be used within the Calvin–Benson cycle. This process lowers the efficiency of photosynthesis, potentially lowering photosynthetic output by 25% in C3 plants. Photorespiration involves a complex network of enzyme reactions that exchange metabolites between chloroplasts, leaf peroxisomes and mitochondria.

<span class="mw-page-title-main">Ribulose 1,5-bisphosphate</span> Chemical compound

Ribulose 1,5-bisphosphate (RuBP) is an organic substance that is involved in photosynthesis, notably as the principal CO2 acceptor in plants. It is a colourless anion, a double phosphate ester of the ketopentose called ribulose. Salts of RuBP can be isolated, but its crucial biological function happens in solution. RuBP occurs not only in plants but in all domains of life, including Archaea, Bacteria, and Eukarya.

A tetrose is a monosaccharide with 4 carbon atoms. They have either an aldehyde functional group in position 1 (aldotetroses) or a ketone functional group in position 2 (ketotetroses).

<span class="mw-page-title-main">Entner–Doudoroff pathway</span> Series of interconnected biochemical reactions

The Entner–Doudoroff pathway is a metabolic pathway that is most notable in Gram-negative bacteria, certain Gram-positive bacteria and archaea. Glucose is the substrate in the ED pathway and through a series of enzyme assisted chemical reactions it is catabolized into pyruvate. Entner and Doudoroff (1952) and MacGee and Doudoroff (1954) first reported the ED pathway in the bacterium Pseudomonas saccharophila. While originally thought to be just an alternative to glycolysis (EMP) and the pentose phosphate pathway (PPP), some studies now suggest that the original role of the EMP may have originally been about anabolism and repurposed over time to catabolism, meaning the ED pathway may be the older pathway. Recent studies have also shown the prevalence of the ED pathway may be more widespread than first predicted with evidence supporting the presence of the pathway in cyanobacteria, ferns, algae, mosses, and plants. Specifically, there is direct evidence that Hordeum vulgare uses the Entner–Doudoroff pathway.

<span class="mw-page-title-main">Calvin cycle</span> Light-independent reactions in photosynthesis

The Calvin cycle,light-independent reactions, bio synthetic phase,dark reactions, or photosynthetic carbon reduction (PCR) cycle of photosynthesis is a series of chemical reactions that convert carbon dioxide and hydrogen-carrier compounds into glucose. The Calvin cycle is present in all photosynthetic eukaryotes and also many photosynthetic bacteria. In plants, these reactions occur in the stroma, the fluid-filled region of a chloroplast outside the thylakoid membranes. These reactions take the products of light-dependent reactions and perform further chemical processes on them. The Calvin cycle uses the chemical energy of ATP and reducing power of NADPH from the light dependent reactions to produce sugars for the plant to use. These substrates are used in a series of reduction-oxidation (redox) reactions to produce sugars in a step-wise process; there is no direct reaction that converts several molecules of CO2 to a sugar. There are three phases to the light-independent reactions, collectively called the Calvin cycle: carboxylation, reduction reactions, and ribulose 1,5-bisphosphate (RuBP) regeneration.

<span class="mw-page-title-main">Glyceraldehyde 3-phosphate</span> Chemical compound

Glyceraldehyde 3-phosphate, also known as triose phosphate or 3-phosphoglyceraldehyde and abbreviated as G3P, GA3P, GADP, GAP, TP, GALP or PGAL, is a metabolite that occurs as an intermediate in several central pathways of all organisms. With the chemical formula H(O)CCH(OH)CH2OPO32-, this anion is a monophosphate ester of glyceraldehyde.

Dihydroxyacetone phosphate (DHAP, also glycerone phosphate in older texts) is the anion with the formula HOCH2C(O)CH2OPO32-. This anion is involved in many metabolic pathways, including the Calvin cycle in plants and glycolysis. It is the phosphate ester of dihydroxyacetone.

<span class="mw-page-title-main">Phosphoenolpyruvic acid</span> Chemical compound

Phosphoenolpyruvate is the carboxylic acid derived from the enol of pyruvate and phosphate. It exists as an anion. PEP is an important intermediate in biochemistry. It has the highest-energy phosphate bond found in organisms, and is involved in glycolysis and gluconeogenesis. In plants, it is also involved in the biosynthesis of various aromatic compounds, and in carbon fixation; in bacteria, it is also used as the source of energy for the phosphotransferase system.

<span class="mw-page-title-main">1,3-Bisphosphoglyceric acid</span> Chemical compound

1,3-Bisphosphoglyceric acid (1,3-Bisphosphoglycerate or 1,3BPG) is a 3-carbon organic molecule present in most, if not all, living organisms. It primarily exists as a metabolic intermediate in both glycolysis during respiration and the Calvin cycle during photosynthesis. 1,3BPG is a transitional stage between glycerate 3-phosphate and glyceraldehyde 3-phosphate during the fixation/reduction of CO2. 1,3BPG is also a precursor to 2,3-bisphosphoglycerate which in turn is a reaction intermediate in the glycolytic pathway.

<span class="mw-page-title-main">2,3-Bisphosphoglyceric acid</span> Chemical compound

2,3-Bisphosphoglyceric acid (2,3-BPG), also known as 2,3-diphosphoglyceric acid (2,3-DPG), is a three-carbon isomer of the glycolytic intermediate 1,3-bisphosphoglyceric acid (1,3-BPG).

<span class="mw-page-title-main">Phosphoenolpyruvate carboxylase</span> Class of enzymes

Phosphoenolpyruvate carboxylase (also known as PEP carboxylase, PEPCase, or PEPC; EC 4.1.1.31, PDB ID: 3ZGE) is an enzyme in the family of carboxy-lyases found in plants and some bacteria that catalyzes the addition of bicarbonate (HCO3) to phosphoenolpyruvate (PEP) to form the four-carbon compound oxaloacetate and inorganic phosphate:

<span class="mw-page-title-main">Bisphosphoglycerate mutase</span> Enzyme

Bisphosphoglycerate mutase is an enzyme expressed in erythrocytes and placental cells. It is responsible for the catalytic synthesis of 2,3-Bisphosphoglycerate (2,3-BPG) from 1,3-bisphosphoglycerate. BPGM also has a mutase and a phosphatase function, but these are much less active, in contrast to its glycolytic cousin, phosphoglycerate mutase (PGM), which favors these two functions, but can also catalyze the synthesis of 2,3-BPG to a lesser extent.

<span class="mw-page-title-main">Phosphoglycerate mutase</span> Class of enzymes

Phosphoglycerate mutase (PGM) is any enzyme that catalyzes step 8 of glycolysis - the internal transfer of a phosphate group from C-3 to C-2 which results in the conversion of 3-phosphoglycerate (3PG) to 2-phosphoglycerate (2PG) through a 2,3-bisphosphoglycerate intermediate. These enzymes are categorized into the two distinct classes of either cofactor-dependent (dPGM) or cofactor-independent (iPGM). The dPGM enzyme is composed of approximately 250 amino acids and is found in all vertebrates as well as in some invertebrates, fungi, and bacteria. The iPGM class is found in all plants and algae as well as in some invertebrate, fungi, and Gram-positive bacteria. This class of PGM enzyme shares the same superfamily as alkaline phosphatase.

<span class="mw-page-title-main">Ribose 5-phosphate</span> Chemical compound

Ribose 5-phosphate (R5P) is both a product and an intermediate of the pentose phosphate pathway. The last step of the oxidative reactions in the pentose phosphate pathway is the production of ribulose 5-phosphate. Depending on the body's state, ribulose 5-phosphate can reversibly isomerize to ribose 5-phosphate. Ribulose 5-phosphate can alternatively undergo a series of isomerizations as well as transaldolations and transketolations that result in the production of other pentose phosphates as well as fructose 6-phosphate and glyceraldehyde 3-phosphate.

<span class="mw-page-title-main">Fructose-bisphosphate aldolase</span>

Fructose-bisphosphate aldolase, often just aldolase, is an enzyme catalyzing a reversible reaction that splits the aldol, fructose 1,6-bisphosphate, into the triose phosphates dihydroxyacetone phosphate (DHAP) and glyceraldehyde 3-phosphate (G3P). Aldolase can also produce DHAP from other (3S,4R)-ketose 1-phosphates such as fructose 1-phosphate and sedoheptulose 1,7-bisphosphate. Gluconeogenesis and the Calvin cycle, which are anabolic pathways, use the reverse reaction. Glycolysis, a catabolic pathway, uses the forward reaction. Aldolase is divided into two classes by mechanism.

Glucose-1,6-bisphosphate synthase is a type of enzyme called a phosphotransferase and is involved in mammalian starch and sucrose metabolism. It catalyzes the transfer of a phosphate group from 1,3-bisphosphoglycerate to glucose-1-phosphate, yielding 3-phosphoglycerate and glucose-1,6-bisphosphate.

<span class="mw-page-title-main">PGAM2</span> Protein-coding gene in the species Homo sapiens

Phosphoglycerate mutase 2 (PGAM2), also known as muscle-specific phosphoglycerate mutase (PGAM-M), is a phosphoglycerate mutase that, in humans, is encoded by the PGAM2 gene on chromosome 7.

<span class="mw-page-title-main">2-Phosphoglycolate</span> Chemical compound

2-Phosphoglycolate (chemical formula C2H2O6P3-; also known as phosphoglycolate, 2-PG, or PG) is a natural metabolic product of the oxygenase reaction mediated by the enzyme ribulose 1,5-bisphosphate carboxylase (RuBisCo).

References

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  6. 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.
  7. Andersson, I. (2008). "Catalysis and regulation in Rubisco". Journal of Experimental Botany. 59 (7): 1555–1568. doi: 10.1093/jxb/ern091 . PMID   18417482.
  8. 1 2 Moran, L. (2007). "The Calvin Cycle: Regeneration". Sandwalk. Retrieved 11 May 2021.
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  1. Note that 3-phosphoglycerate and 2-phosphoglycerate are isomers of one another