5-Fluoroorotic acid

5-Fluoroorotic acid
Names
Preferred IUPAC name
5-Fluoro-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid
Identifiers
CAS Number
  • 703-95-7 checkY
  • 220141-70-8 (monohydrate)
3D model (JSmol)
  • Interactive image
ChemSpider
  • 62912
ECHA InfoCard 100.010.798 Edit this at Wikidata
PubChem CID
  • 69711
UNII
  • 7IA9OUC93E checkY
CompTox Dashboard (EPA)
  • DTXSID90220573 Edit this at Wikidata
InChI
  • InChI=1S/C5H3FN2O4/c6-1-2(4(10)11)7-5(12)8-3(1)9/h(H,10,11)(H2,7,8,9,12)
    Key: SEHFUALWMUWDKS-UHFFFAOYSA-N
  • InChI=1/C5H3FN2O4/c6-1-2(4(10)11)7-5(12)8-3(1)9/h(H,10,11)(H2,7,8,9,12)
    Key: SEHFUALWMUWDKS-UHFFFAOYAV
  • C1(=C(NC(=O)NC1=O)C(=O)O)F
Properties
Chemical formula
 C5H3FN2O4
Molar mass 174.087 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
Chemical compound

5-Fluoroorotic acid (5FOA) is a fluorinated derivative of the pyrimidine precursor orotic acid. It is used in yeast genetics to select for the absence of the URA3 gene, which encodes the enzyme for the decarboxylation of 5-fluoroorotic acid to 5-fluorouracil, a toxic metabolite.[1] It has also been used in diatom selection.[2]

See also

  • 2-FA

References

  1. ^ Boeke, J. D.; Trueheart, J.; Natsoulis, G.; Fink, G. R. (1987). "5-Fluoroorotic acid as a selective agent in yeast molecular genetics". Recombinant DNA Part E. Methods in Enzymology. Vol. 154. pp. 164–75. doi:10.1016/0076-6879(87)54076-9. ISBN 9780121820558. PMID 3323810.
  2. ^ Serif, Manuel; Dubois, Gwendoline; Finoux, Anne-Laure; Teste, Marie-Ange; Jallet, Denis; Daboussi, Fayza (2018-09-25). "One-step generation of multiple gene knock-outs in the diatom Phaeodactylum tricornutum by DNA-free genome editing". Nature Communications. 9 (1). Springer Science and Business Media LLC: 3924. Bibcode:2018NatCo...9.3924S. doi:10.1038/s41467-018-06378-9. ISSN 2041-1723. PMC 6156588. PMID 30254261.
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