A. Kowalczyk et al., Synthesis and characterization of oligodeoxynucleotides containing an N1 beta-hydroxyalkyl adduct of 2 '-deoxyinosine, CHEM RES T, 14(6), 2001, pp. 746-753
Hydroxyethyl adducts arising by the reactions of simple epoxides at the N1
position of adenine nucleosides can deaminate to give the inosine analogues
which, if formed in DNA, are suspected of being highly mutagenic. A method
has been developed for synthesis of oligonucleotides containing N1-adducte
d 2'-deoxyinosines, The 2'-deoxyinosine adduct of 3,4-epoxy-1-butene was pr
epared from (+/-)-4-acetoxy-3-bromo-1-butene and tetraisopropyldisiloxanedi
yl-protected 2'-deoxyinosine with base. The 2'-deoxyinosine derivative was
then incorporated into the oligodeoxynucleotide sequence 5'-d(CGGACXAGAAG)-
3' (X = N1-(1-hydroxy-3-buten-2-yl)-2'deoxyinosine).