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5'-Deoxy-5'-fluoroadenosine

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5′-Deoxy-5′-fluoroadenosine
Names
IUPAC name 5′-Deoxy-5′-fluoroadenosine
Systematic IUPAC name (2R,3R,4S,5S)-2-(6-Amino-9H-purin-9-yl)-5-(fluoromethyl)oxolane-3,4-diol
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C10H12FN5O3/c11-1-4-6(17)7(18)10(19-4)16-3-15-5-8(12)13-2-14-9(5)16/h2-4,6-7,10,17-18H,1H2,(H2,12,13,14)/t4-,6-,7-,10-/m1/s1Key: QPVLKMICBYRPSX-KQYNXXCUSA-N
  • InChI=1/C10H12FN5O3/c11-1-4-6(17)7(18)10(19-4)16-3-15-5-8(12)13-2-14-9(5)16/h2-4,6-7,10,17-18H,1H2,(H2,12,13,14)/t4-,6-,7-,10-/m1/s1Key: QPVLKMICBYRPSX-KQYNXXCUBC
SMILES
  • C1=NC(=C2C(=N1)N(C=N2)3(((O3)CF)O)O)N
Properties
Chemical formula C10H12FN5O3
Molar mass 269.236 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

5′-Deoxy-5′-fluoroadenosine is the first step in the biosynthesis of organic fluorides. It is synthesized by the fluorinase catalyzed addition of a fluoride ion to S-adenosyl-L-methionine, releasing L-methionine as a by product. Purine nucleoside phosphorylase mediates a phosphorolytic cleavage of the adenine base to generate 5-fluoro-5-deoxy-D-ribose-1-phosphate.

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.
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