5'-Deoxy-5'-fluoroadenosine
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Names | |
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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 | |
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Properties | |
C10H12FN5O3 | |
Molar mass | 269.236 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
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.[1] Purine nucleoside phosphorylase mediates a phosphorolytic cleavage of the adenine base to generate 5-fluoro-5-deoxy-D-ribose-1-phosphate.
References
[edit]- ^ 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.