Erythrose 4-phosphate

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Erythrose 4-phosphate
Erythrose 4-phosphate.svg
Erythrose 4-phosphate.png
Names
IUPAC names
[(2R,3R)-2,3-Dihydroxy-4-oxobutyl] phosphate
d-Erythrose 4-(dihydrogen phosphate)
Other names
E4P
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
MeSH erythrose+4-phosphate
PubChem CID
UNII
  • InChI=1S/C4H9O7P/c5-1-3(6)4(7)2-11-12(8,9)10/h1,3-4,6-7H,2H2,(H2,8,9,10)/p-2/t3-,4+/m0/s1 Yes check.svgY
    Key: NGHMDNPXVRFFGS-IUYQGCFVSA-L Yes check.svgY
  • InChI=1/C4H9O7P/c5-1-3(6)4(7)2-11-12(8,9)10/h1,3-4,6-7H,2H2,(H2,8,9,10)/p-2/t3-,4+/m0/s1
    Key: NGHMDNPXVRFFGS-VVTNXMPSBK
  • [O-]P([O-])(=O)OC[C@@H](O)[C@@H](O)C=O
Properties
C4H9O7P
Molar mass 200.084 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Erythrose 4-phosphate is a phosphate of the simple sugar erythrose. It is an intermediate in the pentose phosphate pathway and the Calvin cycle. [1]

The enzyme transaldolase catalyzes the formation of erythrose 4-phosphate and fructose 6-phosphate from sedoheptulose 7-phosphate and glyceraldehyde 3-phosphate. [2] This reaction is a part of the non-oxidative phase of the pentose phosphate pathway.

In the Calvin cycle, the enzyme fructose-bisphosphate aldolase catalyzes the formation of sedoheptulose 1,7-bisphosphate from erythrose 4-phosphate and dihydroxyacetone phosphate. [3]

In addition, it serves as a precursor in the biosynthesis of the aromatic amino acids tyrosine, phenylalanine, and tryptophan. It is used in the first step of the shikimate pathway. At this stage, phosphoenolpyruvate and erythrose-4-phosphate react to form 3-deoxy-D-arabinoheptulosonate-7-phosphate (DAHP), in a reaction catalyzed by the enzyme DAHP synthase.

Biosynthesis of DAHP from phosphoenolpyruvate and erythrose-4-phosphate DAHP synthase reaction.svg
Biosynthesis of DAHP from phosphoenolpyruvate and erythrose-4-phosphate

It also used in 3-hydroxy-1-aminoacetone phosphate biosynthesis, which is a precursor of vitamin B6 in DXP-dependent pathway. Erythrose-4-phosphate dehydrogenase is used to produce erythronate-4-phosphate.

References

  1. ↑ Schramm, M.; Racker, E. (1957). "Formation of Erythrose-4-phosphate and Acetyl Phosphate by a Phosphorolytic Cleavage of Fructose-6-phosphate". Nature. 179 (4574): 1349–1350. Bibcode:1957Natur.179.1349S. doi:10.1038/1791349a0. PMID   13451617. S2CID   1541286.
  2. ↑ Wamelink, M. M. C.; Struys, E. A.; Jakobs, C. (December 2008). "The biochemistry, metabolism and inherited defects of the pentose phosphate pathway: A review". Journal of Inherited Metabolic Disease. 31 (6): 703–717. doi:10.1007/s10545-008-1015-6. ISSN   0141-8955. PMID   18987987.
  3. ↑ Stincone, Anna; Prigione, Alessandro; Cramer, Thorsten; Wamelink, Mirjam M. C.; Campbell, Kate; Cheung, Eric; Olin-Sandoval, Viridiana; Grüning, Nana-Maria; Krüger, Antje; Tauqeer Alam, Mohammad; Keller, Markus A.; Breitenbach, Michael; Brindle, Kevin M.; Rabinowitz, Joshua D.; Ralser, Markus (August 2015). "The return of metabolism: biochemistry and physiology of the pentose phosphate pathway". Biological Reviews. 90 (3): 927–963. doi:10.1111/brv.12140. ISSN   1464-7931. PMC   4470864 . PMID   25243985.
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