• Archives of Pharmacal Research
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• v.23 no.2
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• pp.139-146
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• 2000

7- Bromomethylbenz[a]anthracene is a known mutagen and carcinogen. The two major DNA adducts produced by this carcinogen, i.e., $N^2$-(benz[a]anthracen-7-yl methyl)-2'-deoxyguanosine (2, b[a]$a^2$G) and $N^6$-(benz[a]anthracen-7-ylmethyl)-2'-deoxyadenosine (4, b[a]$a^6$/A), as wel 1 as the simpler benzylated analogs,$N^2$-benzyl-2'deoxyguanosine (1, $bn^2$G) and $N^6$-benzyl-2'-deoxyadenosine (3, $bn^6$/A), were prepared by direct aralkylation of 2'-deoxyguanosine and 2'-deoxyadenosine. To determine the site-specific mutagenicity of these bulky exocyclic amino-substituted adducts, the suitably protected nucleosides were incorporated into 16-base oligodeoxyribonucleotides in place of a normal guanine or adenine residues which respectively are part of the ATG initiation codon for the lac Z' \alpha-complementation gene by using an in situ activation approach and automated phosphite triester synthetic methods. The base composition and the incorporation of the bulky adducts into synthetic oligonucleotides were characterized after purification of the modified oligonucleotides by enzymatic digestion and HPLC analysis.

• Journal of the Korean Chemical Society
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• v.37 no.3
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• pp.355-363
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• 1993

The two deoxyribonucleotides, 5'-d(GAATTCCGGCCA) and 5'-d(CGAGCTGTC), were synthesized on disks of Whatmann chromatography paper (3MM) by the phosphite-triester method. The average yield of the dodecamer and the nonamer that was measured by trityl analysis is 76.1${\%}$ and 86.5${\%}$ respectively. Separation of the synthesized oligodeoxyribonucleotides were purified by HPLC. The two oligodeoxymers'bases were quantified by HPLC with snake venom phosphodiesterase and bacterial alkaline phosphatase. The numbers of bases were equal to the designed ones. The advantage of using a paper disk as a support allows us to synthesize many different oligodeoxyribenucleotides during one synthesis. This method is the most convenient synthetic technique to synthesize oligodeoxyribonucleotides easily and inexpensively in a relatively short time.