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Chemical Compound Review

D-xylulose     (3S,4R)-1,3,4,5- tetrahydroxypentan-2-one

Synonyms: D-Xul, AC1NRDJS, CHEMBL195094, CHEBI:17140, HMDB01644, ...
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Disease relevance of D-xylulose

  • In Escherichia coli, it is known that the vitamin is derived from deoxyxylulose 5-phosphate (an intermediate in the nonmevalonate pathway of isoprenoid biosynthesis) and 4-phosphohydroxy-l-threonine [1].

High impact information on D-xylulose

  • Radioactivity from [2-(14)C]2C-methyl-D-erythritol 2,4-cyclodiphosphate was diverted efficiently to carotenoids by isolated chromoplasts from Capsicum annuum and, thus, was established as an intermediate in the deoxyxylulose phosphate pathway of isoprenoid biosynthesis [2].
  • A gene from Arabidopsis thaliana with similarity to ygbP carries a putative plastid import sequence, which is well in line with the assumed localization of the deoxyxylulose pathway in the plastid compartment of plants [3].
  • Moreover, several microorganisms have genes specifying putative fusion proteins with ygbP and ygbB domains, suggesting that both the YgbP protein and the YgbB protein are involved in the deoxyxylulose pathway [3].
  • The biomimetic epoxy ester[bond]orthoester rearrangement has been applied to a new synthesis of 2-methyl-D-erythritol, a branched five-carbon sugar of importance to the deoxyxylulose pathway of isoprenoid biosynthesis [4].
  • The recently discovered non-mevalonate pathway to isoprenoids, which uses glycolytic intermediates, has been modulated by overexpression of Escherichia coli D-1-deoxyxylulose 5-phosphate synthase (DXS) to increase deoxyxylulose 5-phosphate and, consequently, increase the isoprenoid precursor pool in E. coli [5].

Chemical compound and disease context of D-xylulose


Biological context of D-xylulose

  • Genes with similarity to ygbP and ygbB are present in the genomes of many microorganisms, and their occurrence appears to be correlated with that of the deoxyxylulose pathway of terpenoid biosynthesis [3].

Analytical, diagnostic and therapeutic context of D-xylulose


  1. Vitamin B6 biosynthesis in higher plants. Tambasco-Studart, M., Titiz, O., Raschle, T., Forster, G., Amrhein, N., Fitzpatrick, T.B. Proc. Natl. Acad. Sci. U.S.A. (2005) [Pubmed]
  2. Biosynthesis of terpenoids: YgbB protein converts 4-diphosphocytidyl-2C-methyl-D-erythritol 2-phosphate to 2C-methyl-D-erythritol 2,4-cyclodiphosphate. Herz, S., Wungsintaweekul, J., Schuhr, C.A., Hecht, S., Luttgen, H., Sagner, S., Fellermeier, M., Eisenreich, W., Zenk, M.H., Bacher, A., Rohdich, F. Proc. Natl. Acad. Sci. U.S.A. (2000) [Pubmed]
  3. Cytidine 5'-triphosphate-dependent biosynthesis of isoprenoids: YgbP protein of Escherichia coli catalyzes the formation of 4-diphosphocytidyl-2-C-methylerythritol. Rohdich, F., Wungsintaweekul, J., Fellermeier, M., Sagner, S., Herz, S., Kis, K., Eisenreich, W., Bacher, A., Zenk, M.H. Proc. Natl. Acad. Sci. U.S.A. (1999) [Pubmed]
  4. Synthesis of 2-methyl-D-erythritol via epoxy ester-orthoester rearrangement. Giner, J.L., Ferris, W.V., Mullins, J.J. J. Org. Chem. (2002) [Pubmed]
  5. Metabolic engineering of carotenoid accumulation in Escherichia coli by modulation of the isoprenoid precursor pool with expression of deoxyxylulose phosphate synthase. Matthews, P.D., Wurtzel, E.T. Appl. Microbiol. Biotechnol. (2000) [Pubmed]
  6. Isopentenyl diphosphate biosynthesis via a mevalonate-independent pathway: isopentenyl monophosphate kinase catalyzes the terminal enzymatic step. Lange, B.M., Croteau, R. Proc. Natl. Acad. Sci. U.S.A. (1999) [Pubmed]
  7. A high-performance liquid chromatography method for the analysis of intermediates of the deoxyxylulose phosphate pathway. Raschke, M., Fellermeier, M., Zenk, M.H. Anal. Biochem. (2004) [Pubmed]
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