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A1757

Sigma-Aldrich

6-Azauracil

≥98%

Synonym(s):

6-AU, 1,2,4-Triazine-3,5(2H,4H)-dione, 3,5-Dihydroxy-1,2,4-triazine, 6-Aza-2,4-dihydroxypyrimidine

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About This Item

Empirical Formula (Hill Notation):
C3H3N3O2
CAS Number:
461-89-2
Molecular Weight:
113.07
Beilstein:
116472
EC Number:
207-318-0
MDL number:
MFCD00006456
UNSPSC Code:
41106305
PubChem Substance ID:
24890584
NACRES:
NA.51

Assay

≥98%

form

powder

mp

274-275 °C (lit.)

solubility

1 M NH4OH: 50 mg/mL, clear to slightly hazy, colorless to light yellow-green

SMILES string

O=C1NN=CC(=O)N1

InChI

1S/C3H3N3O2/c7-2-1-4-6-3(8)5-2/h1H,(H2,5,6,7,8)

InChI key

SSPYSWLZOPCOLO-UHFFFAOYSA-N

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Application

6-Azauracil has been used as a transcriptional inhibitor to study its effects on the deletion of termination and polyadenylation protein (Tpa1) and Mag1 on cell viability. It has also been used as an orotidine-5′-monophosphate decarboxylase (OMPdecase) inhibitor in minimal media for determining the OMPdecase activity.

Biochem/physiol Actions

6-Azauracil (6-AU) is a pyrimidine analog of uracil and exhibits antitumor activity. It inhibits the growth of various microorganisms by depleting intracellular guanosine triphosphate (GTP) and uridine triphosphate (UTP) nucleotide pools.

Storage Class Code

11 - Combustible Solids

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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methods in molecular biology
steroid receptor methods (2001)
Sittinan Chanarat et al.
Genes & development, 25(11), 1147-1158 (2011-05-18)
Different steps in gene expression are intimately linked. In Saccharomyces cerevisiae, the conserved TREX complex couples transcription to nuclear messenger RNA (mRNA) export. However, it is unknown how TREX is recruited to actively transcribed genes. Here, we show that the
Kostyantyn V Dmytruk et al.
Metabolic engineering, 13(1), 82-88 (2010-11-03)
Currently, the mutant of the flavinogenic yeast Candida famata dep8 isolated by classic mutagenesis and selection is used for industrial riboflavin production. Here we report on construction of a riboflavin overproducing strain of C. famata using a combination of random
Mihajlo Etinski et al.
Physical chemistry chemical physics : PCCP, 12(48), 15665-15671 (2010-08-04)
The photophysical properties of 6-azauracil were studied by means of ab initio quantum chemical methods. On the basis of our calculations we propose here the following mechanism for the lack of fluorescence and the high triplet quantum yield that was
Valérie Declerck et al.
The Journal of organic chemistry, 76(2), 708-711 (2010-12-25)
A short and efficient synthesis of the previously unknown N-aminoazetidinecarboxylic acid has been established using a photochemical [2 + 2] cycloaddition strategy starting from 6-azauracil. Chiral derivatization with a nonracemic oxazolidinone provided access to both enantiomers of the title product.
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