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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

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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
P Pongsaensook et al.
Mutation research, 377(1), 27-36 (1997-06-09)
The TK6 human B lymphoblastoid cell line contains two easily and widely used selectable markers: the X-linked, hemizygous hprt locus, and the heterozygous tk locus on chromosome 17q. In this study, rare APRT heterozygotes were directly isolated from the TK6
João Paulo Gobbo et al.
The journal of physical chemistry. B, 116(48), 14000-14007 (2012-11-15)
The photophysics of 8-azaadenine (8-AA) has been studied with the CASPT2//CASSCF protocol and ANO-L double-ζ basis sets. Stationary equilibrium structures, surface crossings, minimum energy paths, and linear interpolations have been used to study possible mechanisms to populate the lowest triplet
D B Busch et al.
Mutation research, 383(2), 91-106 (1997-03-12)
Rodent ultraviolet light (UV)-sensitive mutant cells in complementation groups (CGs) 1 and 4 normally are known for their extraordinary (approximately 80-100 x) sensitivity to mitomycin C (MMC), although some CG1 mutants with reduced MMC sensitivity were previously reported (Stefanini et
Giuliana Biagi et al.
European journal of medicinal chemistry, 38(11-12), 983-990 (2003-12-04)
Several 9-benzyl-N6-cycloalkyl-2-phenyladenines, 9-benzyl-N6-cycloalkyl-2-phenyl-8-azaadenines and 4-cycloalkylamino-1-benzyl-6-phenyl-1H-1,2,3-triazolo[4,5-c]pyridines were prepared and assayed as A1 adenosine receptor ligands. The 1H-1,2,3-triazolo[4,5-c]pyridines were obtained starting from N,N-diethyl-1-benzyl-4-carboxyamido-5-methyl-1H-1,2,3-triazole by lithiation in anhydrous tetrahydrofurane in the presence of benzonitrile. The usual work up afforded the isolation of 1-benzyl-6-phenyl-1H-1,2,3-triazolo[4,5-c]pyridin-4-one
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