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F5013

Sigma-Aldrich

5-Fluoroorotic acid hydrate

≥98%

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Synonym(s):
2,6-Dihydroxy-5-fluoropyrimidine-4-carboxylic acid, 5-Fluorouracil-4-carboxylic acid
Empirical Formula (Hill Notation):
C5H3FN2O4 · xH2O
CAS Number:
207291-81-4
Molecular Weight:
174.09 (anhydrous basis)
EC Number:
211-876-0
MDL number:
MFCD00150658
UNSPSC Code:
12352204
PubChem Substance ID:
24894877
NACRES:
NA.32

biological source

synthetic

Quality Level

200

Assay

≥98%

form

powder

technique(s)

cell culture | plant: suitable

mp

278 °C (dec.) (lit.)

solubility

4 M NH4OH: 50 mg/mL, clear, colorless to light yellow

storage temp.

−20°C

SMILES string

OC(C(NC(N1)=O)=C(F)C1=O)=O.[H]O[H]

InChI

1S/C5H3FN2O4.H2O/c6-1-2(4(10)11)7-5(12)8-3(1)9;/h(H,10,11)(H2,7,8,9,12);1H2

InChI key

LODRRYMGPWQCTR-UHFFFAOYSA-N

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Application

5-Fluoroorotic acid hydrate has also been used as a counter-selection agent to screen L. lactis (multi) peptidase knockout mutants and C. albicans. It has been used in synthesis of 5-fluoroorotidine 5′-monophosphate (FOMP).
Useful in the selection of orotidine-5′-phosphate decarboxylase mutants of Saccharomyces cerevisiae.

Biochem/physiol Actions

5-Fluoroorotic acid is a selective inhibitor of rRNA synthesis in mammals.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H315,H319,H335

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Inhibition of ribosomal ribonucleic acid maturation in rat liver by 5-fluoroorotic acid resulting in the selective labeling of cytoplasmic messenger ribonucleic acid
Wilkinson D S, et al.
The Journal of Biological Chemistry, 246(21), 6418-6427 (1971)
Chenxi Huang et al.
Applied and environmental microbiology, 86(18) (2020-07-19)
Large-scale mass spectrometry-based peptidomics for bioactive-peptide discovery is relatively unexplored because of challenges in intracellular peptide extraction and small-peptide identification. Here, we present an analytical pipeline for large-scale intracellular peptidomics of Lactococcus lactis It entails an optimized sample preparation protocol
Mechanism of the orotidine 5?-monophosphate decarboxylase-catalyzed reaction: Effect of solvent viscosity on kinetic constants
Wood B M, et al.
Biochemistry, 48(24), 5510-5517 (2009)
Lakshmi Sreekumar et al.
Genetics, 212(4), 1121-1132 (2019-05-31)
The diploid budding yeast Candida albicans harbors unique CENPA-rich 3- to 5-kb regions that form the centromere (CEN) core on each of its eight chromosomes. The epigenetic nature of these CENs does not permit the stabilization of a functional kinetochore
Jiaxin Gao et al.
Nature communications, 9(1), 4495-4495 (2018-10-31)
Fungal infections by drug-resistant Candida albicans pose a global public health threat. However, the pathogen's diploid genome greatly hinders genome-wide investigations of resistance mechanisms. Here, we develop an efficient piggyBac transposon-mediated mutagenesis system using stable haploid C. albicans to conduct

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