From Wikipedia, the free encyclopedia
5-Fluoroorotic acid
Names
Preferred IUPAC name
5-Fluoro-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid
Identifiers
ChemSpider
ECHA InfoCard
100.010.798
UNII
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
C 5 H 3 F N 2 O 4
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).
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]
^ 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 .
^ 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 .