5-Fluoro-5-deoxy-D-ribose 1-phosphate
Names
IUPAC name
5-Deoxy-5-fluoro-D-ribofuranosyl dihydrogen phosphate
Preferred IUPAC name
(2Ξ,3R,4S,5S)-5-(Fluoromethyl)-3,4-dihydroxyoxolan-2-yl dihydrogen phosphate
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C5H10FO7P/c6-1-2-3(7)4(8)5(12-2)13-14(9,10)11/h2-5,7-8H,1H2,(H2,9,10,11)/t2-,3-,4-,5?/m1/s1
    Key: LUQFMENCTWEBSQ-SOOFDHNKSA-N
  • O[C@@H]1[C@H](O)[C@@H](CF)OC1OP(=O)(O)O
Properties
C5H10FO7P
Molar mass 232.100 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. Bibcode:2002Natur.416..279O. doi:10.1038/416279a. PMID 11907567. S2CID 4415511.
  2. ↑ Hai Deng; Stuart M. Cross; Ryan P. McGlinchey; John T.G. Hamilton; David 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.
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