Abstract:
:The 2'-deoxyguanosine adduct of the dietary mutagen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) has been synthesized and incorporated into DNA using solid state synthesis technology. The key step to obtaining the C8-dG adduct is a palladium (Xantphos-chelated)-catalyzed N-arylation (Buchwald-Hartwig reaction) of PhIP by a suitably protected 8-bromo-2'-deoxyguanosine derivative. The reaction proceeded in good yield without complicating side products, and the adduct was converted to the required 5'-O-DMT-3'-O-phosphoramidite by standard methods. This modified deoxynucleoside was used to synthesize three oligodeoxynucleotides in which the C8-PhIP-dG adduct was incorporated at a single site. The oligomers were purified by reverse phase HPLC and characterized by mass spectrometry.
journal_name
Chem Res Toxicoljournal_title
Chemical research in toxicologyauthors
Bonala R,Torres MC,Iden CR,Johnson Fdoi
10.1021/tx0600191subject
Has Abstractpub_date
2006-06-01 00:00:00pages
734-8issue
6eissn
0893-228Xissn
1520-5010journal_volume
19pub_type
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