Chemistry:Erythrose 4-phosphate

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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
MeSH erythrose+4-phosphate
UNII
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).
Infobox references
Tracking categories (test):

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

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 4-phospho-D-erythronic acid:[4][5]

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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. doi:10.1038/1791349a0. PMID 13451617. Bibcode1957Natur.179.1349S. https://www.nature.com/articles/1791349a0. 
  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" (in en). Journal of Inherited Metabolic Disease 31 (6): 703–717. doi:10.1007/s10545-008-1015-6. ISSN 0141-8955. PMID 18987987. https://onlinelibrary.wiley.com/doi/10.1007/s10545-008-1015-6. 
  3. Stincone, Anna; Prigione, Alessandro; Cramer, Thorsten; Wamelink, Mirjam M. C.; Campbell, Kate; Cheung, Eric; Olin-Sandoval, Viridiana; Grüning, Nana-Maria et al. (August 2015). "The return of metabolism: biochemistry and physiology of the pentose phosphate pathway" (in en). Biological Reviews 90 (3): 927–963. doi:10.1111/brv.12140. ISSN 1464-7931. PMID 25243985. 
  4. Enzyme 1.2.1.72 at KEGG Pathway Database.
  5. "Involvement of the gapA- and epd (gapB)-encoded dehydrogenases in pyridoxal 5'-phosphate coenzyme biosynthesis in Escherichia coli K-12". J. Bacteriol. 180 (16): 4294–9. 1998. doi:10.1128/JB.180.16.4294-4299.1998. PMID 9696782.