期刊
CHEMICAL RESEARCH IN TOXICOLOGY
卷 19, 期 6, 页码 734-738出版社
AMER CHEMICAL SOC
DOI: 10.1021/tx0600191
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资金
- Intramural NIH HHS Funding Source: Medline
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.
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