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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:
Molecular Weight:
113.07
Beilstein:
116472
EC Number:
MDL number:
UNSPSC Code:
41106305
PubChem Substance ID:
NACRES:
NA.51

Quality Level

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

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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
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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
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The EMBO journal, 26(6), 1552-1559 (2007-03-03)
Capping of nascent pre-mRNAs is thought to be a prerequisite for productive elongation and associated serine 2 phosphorylation of the C-terminal domain (CTD) of RNA polymerase II (PolII). The mechanism mediating this link is unknown, but is likely to include
Mattias Carlsson et al.
PloS one, 13(5), e0196840-e0196840 (2018-05-09)
Purine and pyrimidine analogues have important uses in chemotherapies against cancer, and a better understanding of the mechanisms that cause resistance to these drugs is therefore of importance in cancer treatment. In the yeast Saccharomyces cerevisiae, overexpression of the HAM1

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