Synthesis and characterization of oligodeoxynucleotides containing an N1 beta-hydroxyalkyl adduct of 2 '-deoxyinosine

Citation
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
Citations number
28
Categorie Soggetti
Pharmacology & Toxicology
Journal title
CHEMICAL RESEARCH IN TOXICOLOGY
ISSN journal
0893228X → ACNP
Volume
14
Issue
6
Year of publication
2001
Pages
746 - 753
Database
ISI
SICI code
0893-228X(200106)14:6<746:SACOOC>2.0.ZU;2-S
Abstract
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).