Erythrose 4-phosphate

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]

Erythrose 4-phosphate

Names
IUPAC name (2R,3R)-2,3-dihydroxy-4-oxobutyl phosphate
Other names E4P
Identifiers
CAS Number	585-18-2 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:48153 N
ChemSpider	4573609 Y
MeSH	erythrose+4-phosphate
PubChem CID	5459862
UNII	2156QF7O8M Y
InChI 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 Y Key: NGHMDNPXVRFFGS-IUYQGCFVSA-L Y 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
SMILES [O-]P([O-])(=O)OC[C@@H](O)[C@@H](O)C=O
Properties
Chemical formula	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). N verify (what is YN ?) Infobox references

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 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.