855529

Sigma-Aldrich

8-Azaadenine

97%

Synonym(s):
8-Aza-6-aminopurine, 6-Amino-8-azapurine
Empirical Formula (Hill Notation):
C4H4N6
CAS Number:
Molecular Weight:
136.11
Beilstein/REAXYS Number:
141551
EC Number:
MDL number:
PubChem Substance ID:

assay

97%

mp

>300 °C (lit.)

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.

Certificate of Analysis

Certificate of Origin

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...
J Harwood et al.
Human molecular genetics, 2(2), 165-171 (1993-02-01)
The nature of recessive mutations at the autosomal locus encoding the purine salvage enzyme adenine phosphoribosyl transferase (APRT) was analyzed in a highly malignant human tumor cell line (the colorectal carcinoma line SW620). Mutant strains resistant to the purine analog...

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