Orotidine

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Orotidine
Chemical structure of orotidine
Ball-and-stick model of orotidine
Names
IUPAC name
4-Pyrimidinecarboxylic acid, 1,2,3,6-tetrahydro-2,6-dioxo-3-beta-D-ribofuranosyl-
Other names
3-Ribofuranosylorotic acid, 6-Carboxyuridine, orotate riboside
Identifiers
3D model (JSmol)
ChemSpider
Properties
C10H12N2O8
Molar mass 288.213 g/mol
Melting point 200 °C (392 °F; 473 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Orotidine is a nucleoside formed by attaching orotic acid to a ribose ring via a β-N1-glycosidic bond. It is found in bacteria, fungi and plants. It was first isolated in 1951 from the fungus Neurospora by A. Michael Michelson, William Drell, and Herschel K. Mitchell.[1] In humans, orotidine occurs as its 5'-phosphate (orotidylic acid), which is an intermediate in pyrimidine nucleotide biosynthesis (cytidine and uridine) that are found in nucleic acids. Orotidine itself is not a component of nucleic acid. Large amounts of orotidine are excreted in the urine of cancer patients treated with 6-azauridine.

The symbol commonly used for orotidine is O or Ord.

Notes[edit]

  1. ^ A. Michael Michelson; William Drell; Herschel K. Mitchell (1951). "A new ribose nucleoside from Neurospora: "orotidine"". Proc Natl Acad Sci USA. 37 (7): 396–399. doi:10.1073/pnas.37.7.396. PMC 1063384Freely accessible. PMID 14853953.