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Erythrose 4-phosphate

From Wikipedia, the free encyclopedia
Erythrose 4-phosphate
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
MeSHerythrose+4-phosphate
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 checkY
    Key: NGHMDNPXVRFFGS-IUYQGCFVSA-L checkY
  • 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 mass200.084 g/mol
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Chemical compound

Erythrose 4-phosphate is aphosphate of the simple sugarerythrose. It is an intermediate in thepentose phosphate pathway and theCalvin cycle.[1]

The enzymetransaldolase catalyzes the formation of erythrose 4-phosphate andfructose 6-phosphate fromsedoheptulose 7-phosphate andglyceraldehyde 3-phosphate.[2] This reaction is a part of the non-oxidative phase of the pentose phosphate pathway.

In the Calvin cycle, the enzymefructose-bisphosphate aldolase catalyzes the formation of sedoheptulose 1,7-bisphosphate from erythrose 4-phosphate anddihydroxyacetone phosphate.[3]

In addition, it serves as a precursor in the biosynthesis of the aromatic amino acidstyrosine,phenylalanine, andtryptophan. It is used in the first step of theshikimate pathway. At this stage,phosphoenolpyruvate and erythrose-4-phosphate react to form3-deoxy-D-arabinoheptulosonate-7-phosphate (DAHP), in a reaction catalyzed by the enzymeDAHP synthase.

Biosynthesis of DAHP from phosphoenolpyruvate and erythrose-4-phosphate

It also used in3-hydroxy-1-aminoacetone phosphate biosynthesis, which is a precursor ofvitamin B6 inDXP-dependent pathway.Erythrose-4-phosphate dehydrogenase is used to produceerythronate-4-phosphate.

References

[edit]
  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.
Oxidative
Nonoxidative
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