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A5883

Sigma-Aldrich

8-Azaadenine

≥99%

Synonym(s):

6-Amino-8-azapurine, 8-Aza-6-aminopurine

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About This Item

Empirical Formula (Hill Notation):
C4H4N6
CAS Number:
1123-54-2
Molecular Weight:
136.11
Beilstein:
141551
EC Number:
214-375-5
MDL number:
MFCD00005697
UNSPSC Code:
12352202
PubChem Substance ID:
24891030

Assay

≥99%

form

powder

mp

>300 °C (lit.)

solubility

1 M NaOH: 50 mg/mL, clear, colorless to faintly yellow

storage temp.

2-8°C

SMILES string

Nc1ncnc2nn[nH]c12

InChI

1S/C4H4N6/c5-3-2-4(7-1-6-3)9-10-8-2/h1H,(H3,5,6,7,8,9,10)

InChI key

HRYKDUPGBWLLHO-UHFFFAOYSA-N

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General description

Base pairs of azaadenine with thymine (and azaguanine with cytosine) are found by ab initio calculation to be up to 7 kcal/mol more stable than natural AT (and GC) base pairs.

Storage Class Code

13 - Non 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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A Sahota et al.
Mutation research, 180(1), 81-87 (1987-09-01)
Spontaneous and ethyl methanesulfate induced mutants of Saccharomyces cerevisiae, with partial and complete deficiency of adenine phosphoribosyltransferase (APRT, EC 2.4.2.7), were isolated by selection for resistance to 8-azaadenine. Matings between totally deficient mutants and tester strain resulted in diploid heterozygotes
G Biagi et al.
Farmaco (Societa chimica italiana : 1989), 50(1), 13-19 (1995-01-01)
Comparison of the affinity towards adenosine receptors of 2-phenyl-8-azaadenosines, bearing a lipophilic substituent on N(6), with the corresponding 2-phenyl-8-azaadenines was carried out. The compounds have good A1 affinity and high A1 selectivity. The obtained Ki(rib)/Ki(benz) ratios for A1 receptors, which
Giuliana Biagi et al.
Farmaco (Societa chimica italiana : 1989), 57(3), 221-233 (2002-05-07)
erythro-2-Phenyl-9-(2-hydroxy-3-nonyl)adenine and its 8-aza analog were prepared and showed a very high inhibitory activity towards adenosine deaminase (ADA), with Ki 0.55 and 1.67 nM, respectively, and high affinity for A1 adenosine receptors, with Ki 28 and 2.8 nM, respectively. To
D J Chen et al.
Environmental mutagenesis, 4(4), 457-467 (1982-01-01)
A chinese hamster ovary (CHO) cell line heterozygous at the adenine phosphoribosyl transferase (APRT) locus was used for selection of induced mutants resistant to 8-azaadenine (8AA), 6-thioguanine (6TG), ouabain (OUA), emetine (EMT) and diphtheria toxin (DIP). The expression times necessary
A E Simon et al.
Molecular and cellular biology, 3(10), 1703-1710 (1983-10-01)
A two-step model to explain the high frequency of mutation at the diploid adenine phosphoribosyltransferase (aprt) locus in CHO cells has been proposed previously (Simon et al., Mol. Cell. Biol. 2:1126-1133, 1982). This model indicates that two distinct classes of
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