5-Fluoro-5-deoxy-D-ribose-1-phosphate

5-Fluoro-5-deoxy-D-ribose-1-phosphate

Names
IUPAC name 5-Deoxy-5-fluoro-1-O-phosphonato-D-ribofuranose
Identifiers
ChemSpider	21169315 (dianion)
Jmol interactive 3D	Image
PubChem	49859615 (dianion)
SMILES O[C@@H]1[C@H](O)[C@@H](CF)OC1OP(=O)(O)O
Properties
Chemical formula	C5H10FO7P
Molar mass	232.10 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

5-Fluoro-5-deoxy-D-ribose-1-phosphate is metabolite formed during the biosynthesis of organofluorides. It is formed by the purine nucleoside phosphorylase mediated phosphorolytic cleavage of 5'-deoxy-5'-fluoroadenosine.^[1] It is isomerized to 5-fluoro-5-deoxy-ribulose-1-phosphate which is then cleaved by an aldolase to release fluoroacetaldehyde.^[2]

References

1. O'Hagan D, Schaffrath C, Cobb SL, Hamilton JT, Murphy CD (2002). "Biochemistry: biosynthesis of an organofluorine molecule". Nature. 416 (6878): 279. doi:10.1038/416279a. PMID 11907567.
2. Hai Deng, Stuart M. Cross, Ryan P. McGlinchey, John T.G. Hamilton, David O'Hagan; Cross; McGlinchey; Hamilton; O'Hagan (2008). "In Vitro Reconstituted Biotransformation of 4-Fluorothreonine from Fluoride Ion: Application of the Fluorinase". Chemistry and Biology 15 (12): 1268–1276. doi:10.1016/j.chembiol.2008.10.012. PMID 19101471.