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Synthesis of the minor acrolein adducts of 2′-deoxyguanosine and their generation in oligomeric DNA

✍ Scribed by Yanhe Huang; M. Cecilia Torres; Charles R. Iden; Francis Johnson

Publisher
Elsevier Science
Year
2003
Tongue
English
Weight
209 KB
Volume
31
Category
Article
ISSN
0045-2068

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✦ Synopsis

Acrolein, a known mutagen, undergoes reaction in vitro under physiological conditions with both 2(')-deoxyguanosine and native DNA to give rise to exocyclic adducts of the 5,6,7,8-tetrahydropyrimido[1,2-a]purine-10(3H)-one class having an hydroxy group at either the 6 or the 8 position. Previously we have shown that the 8-hydroxy derivative in a bacterial system has very low mutagenicity probably because in double-stranded DNA this residue exists in the open-chain aldehydic form [N(2)-(3-oxopropyl)-2(')-deoxyguanosine] (3). To continue our investigation in this area, we needed ample supplies of the 6-hydroxy isomers. This current paper describes high-yield simple methods for the synthesis in bulk of the 6-hydroxy adduct 1 and its incorporation into DNA oligomers. The basic methods for the synthesis of the adduct 1, involve 1-substitution of dG derivatives with a 3-butenyl group, dihydroxylation of the olefin with osmium tetroxide and N-methylmorpholine N-oxide, then diol cleavage with periodate ion after incorporation of the 1-(3,4-diacetoxybutyl)-2(')-deoxyguanosine into oligomeric DNA.

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