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Xylulose 5-phosphate

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Xylulose 5-phosphate
Names
IUPAC name 5-O-Phosphonato-D-xylulose
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
MeSH xylulose-5-phosphate
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C5H11O8P/c6-1-3(7)5(9)4(8)2-13-14(10,11)12/h4-6,8-9H,1-2H2,(H2,10,11,12)/p-2/t4-,5-/m1/s1Key: FNZLKVNUWIIPSJ-RFZPGFLSSA-L
SMILES
  • P()(=O)OC(O)(O)C(=O)CO
Properties
Chemical formula C5H11O8P
Molar mass 230.109 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

D-Xylulose 5-phosphate (D-xylulose-5-P) is an intermediate in the pentose phosphate pathway. It is a ketose sugar formed from ribulose-5-phosphate by ribulose-5-phosphate epimerase. In the non-oxidative branch of the pentose phosphate pathway, xylulose-5-phosphate acts as a donor of two-carbon ketone groups in transketolase reactions.

Xylulose-5-phosphate also plays a crucial role in the regulation of glycolysis through its interaction with the bifunctional enzyme PFK2/FBPase2. Specifically, it activates protein phosphatase, which then dephosphorylates PFK2/FBPase2. This inactivates the FBPase2 activity of the bifunctional enzyme and activates its PFK2 activity. As a result, the production of fructose 2,6-bisphosphate increases, ultimately leading to an upregulation of glycolysis.

Although previously thought of mainly as an intermediary in the pentose phosphate pathway, recent research reported that the sugar also has a role in gene expression, mainly by promoting the ChREBP transcription factor in the well-fed state. However, more recent study showed that D-glucose-6-phosphate, rather than D-xylulose-5-phosphate, is essential for the activation of ChREBP in response to glucose.

References

  1. Stincone A, Prigione A, Cramer T, Wamelink MM, Campbell K, Cheung E, et al. (August 2015). "The return of metabolism: biochemistry and physiology of the pentose phosphate pathway". Biological Reviews of the Cambridge Philosophical Society. 90 (3): 927–963. doi:10.1111/brv.12140. PMC 4470864. PMID 25243985.
  2. Nelson, David L.; Cox, Michael M.; Nelson, David L. (2013). Lehninger, Albert L. (ed.). Lehninger principles of biochemistry (6th ed.). Basingstoke: Macmillan Higher Education. p. 606. ISBN 978-1-4292-3414-6.
  3. Uyeda K (June 2021). "Short- and Long-Term Adaptation to Altered Levels of Glucose: Fifty Years of Scientific Adventure". Annual Review of Biochemistry. 90 (1): 31–55. doi:10.1146/annurev-biochem-070820-125228. PMID 34153217.
  4. Kabashima T, Kawaguchi T, Wadzinski BE, Uyeda K (April 2003). "Xylulose 5-phosphate mediates glucose-induced lipogenesis by xylulose 5-phosphate-activated protein phosphatase in rat liver". Proceedings of the National Academy of Sciences of the United States of America. 100 (9): 5107–5112. Bibcode:2003PNAS..100.5107K. doi:10.1073/pnas.0730817100. PMC 154306. PMID 12684532.
  5. Iizuka K, Horikawa Y (August 2008). "ChREBP: a glucose-activated transcription factor involved in the development of metabolic syndrome". Endocrine Journal. 55 (4): 617–624. doi:10.1507/endocrj.k07e-110. PMID 18490833.
  6. Dentin R, Tomas-Cobos L, Foufelle F, Leopold J, Girard J, Postic C, Ferré P (January 2012). "Glucose 6-phosphate, rather than xylulose 5-phosphate, is required for the activation of ChREBP in response to glucose in the liver". Journal of Hepatology. 56 (1): 199–209. doi:10.1016/j.jhep.2011.07.019. PMID 21835137.
Pentose phosphate pathway metabolic intermediates
Oxidative
Nonoxidative
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