N - -adenine

RSCH3, methionine RNH2> N -guanine- and N -adenine-nucleosides or -nucleic acids RCH, C8-guanine-nucleosides or -nucleic acids. The dashed arrow indicates a proposed pathway. 

Koivisto, P, Kostiainen, R., Kilpelainen I., Steinby, K. Peltonen, K. (1995) Preparation, characterization and 32p-postlabeling of butadiene monoepoxide N -adenine adducts. Carcinogenesis, 16,2999-3007... 

Koivisto, P, Adler, I.-D., Sorsa, M. Peltonen, K. (1996) Inlralation exposure of rats and mice to 1,3-butadiene induces N >-adenine adducts of epoxybutene detected by zp.postlabeling and HPLC. Environ. Health Perspect.. 104 (Suppl. 3), 655-657... 

Hakimelahi has reported a novel strategy for the synthesis of N -purine acyclic nucleosides, in which the key step involves the reaction of [2-(p-methoxyphenyloxy)ethoxyl]methyl chloride and iV -tritylated nucleobases, followed by concomitant self-detritylation. 7-[(2-Hydroxyethoxy)methyl] guanine was phosphorylated by both HSV- and Vero-cell thymidine kinases to yield (92), and was found to have more potent cellular toxicity than acyclovir, while the adenine parent was phosphorylated by neither kinase. In addition, the N -adenine acyclic nucleoside phosphonate (93) was synthesised by alkylation of adenine with 3-bromopropionitrile to yield AT -(cyanoethyl)adenine, which upon... 

N adenine derivatives, phenyl urea compounds basic effect of numerous known cytokinins may be at level of protein synthesis... 

The fact that purine bases could be used directly for nucleotide and nucleic acid i thesis was first established by the use of labeled compounds. Plentl and Schoenheimer (5) were not able to demonstrate incorporation of N- anine into nucleic acids of rat viscera in 1944, but Brown later was able to show that it was utilized by mice. (It is now known that guanine is degraded more rapidly in rats than in mice.) Brown and his colleagues (4, 5) also demonstrated the incorporation of N-adenine into nucleic acids, and between 1948 and 1954 numerous studies were made of the incorporation of N- or >KJ-labeled purines into nucleotides and nucleic acids (see reference g). 

Brown and co-workers in 1948 (S) fed N-adenine to rats and found that both adenine and guanine in the visceral nucleic acids were labeled and that the specific activity of guanine was 60% that of adenine. Partly because of rapid deamination of guanine, especially in rats, similar studies with N-guanine did not show a corresponding synthesis of labeled nucleic acid adenine. However, later studies by Abrams and Bentley (4), with slices of erythroid bone marrow from rabbits, demonstrated conversion of guanine to adenine and at least some mutual interconversion of adenine and guanine has been found in most animal cells by the use of suflSciently sensitive techniques. 

Fig. 2 Methyltransferase-directed N -adenine alkylation of DNA by 5 -[(5)-[(3S)-3-amino-3-carboxylpropyl]( )-pent-2-en-4-ynylsulfonio]-5 -deoxy-adenosine and subsequent CuAAC reaction with an azido-modified reporter group [83]...

C20H2 8C1 Cu2N2o02o f Tetra-/n adenine-diaguodicopper(II) perchlorate dihydrate, 39B, 751... 

Fox, I. H., Meade, J.C. and Kelley, W. N. Adenine phosphoribosyl-transferase deficiency Report of a second family. Amer. J. Med. (in press). 

Interactions of metal ions and their complexes with nucleic acids are of primary importance. The details are not known yet. However, the experimental data suggest that after dissociation of Cl", the cisplatin cationic species forms coordinate bonds with the nitrogen atoms of nucleic bases in vitro, this includes bonds with 7-N guanine, 1-N and 7-N adenine, and 3-N cytosine. ... 

It is known that I-N adenine and 3-N cytosine are hydrogen-bonded inside the DNA structure. The strongest hydrogen bond is formed between 7-N guanine and platinum. 

Active cytokinins are N -adenine derivatives, either the free base or riboside or ribonucleotide. In addition to zeatin (known also to occur as the riboside or ribonucleotide) there is evidence for the natural occurrence of N -methylaminopurine, 6-(A -isopentenyl amino)-purine (IPA) and other and as yet unidentified cytokinins. 

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