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A1757

Sigma-Aldrich

6-Azauracil

≥98%

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

Quality Level

100

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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Clinical studies of 6-azauracil
Shnider BI, et al.
Cancer Research, 20(1), 28-33 (1960)
Hai-Ning Du et al.
Genes & development, 22(20), 2786-2798 (2008-10-17)
Set2-mediated H3 K36 methylation is an important histone modification on chromatin during transcription elongation. Although Set2 associates with the phosphorylated C-terminal domain (CTD) of RNA polymerase II (RNAPII), the mechanism of Set2 binding to chromatin and subsequent exertion of its
Rahul V Nene et al.
PLoS genetics, 14(1), e1007170-e1007170 (2018-01-11)
Defects in the genes encoding the Paf1 complex can cause increased genome instability. Loss of Paf1, Cdc73, and Ctr9, but not Rtf1 or Leo1, caused increased accumulation of gross chromosomal rearrangements (GCRs). Combining the cdc73Δ mutation with individual deletions of
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
methods in molecular biology
steroid receptor methods (2001)
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