Synthesis of 8-(Hydroxymethyl)-3,N4-etheno-2‘-deoxycytidine, a Potential Carcinogenic Glycidaldehyde Adduct, and Its Site-Specific Incorporation into DNA Oligonucleotides
- 25 February 2000
- journal article
- research article
- Published by American Chemical Society (ACS) in Chemical Research in Toxicology
- Vol. 13 (3) , 208-213
- https://doi.org/10.1021/tx990181m
Abstract
The previously unreported glycidaldehyde adduct, 8-(hydroxymethyl)-3,N4-etheno-2‘-deoxycytidine (8-HM-εdC), has been synthesized for the first time by reaction of 2‘-deoxycytidine with bromoacetaldehyde at pH 4.5, followed by reduction with sodium borohydride. The adduct was characterized by UV, MS, and NMR. The compound was stable to neutral and acidic conditions but not in alkaline solution. The corresponding phosphoramidite was synthesized in good yield from the intermediate, 3,N4-ethenocarbaldehyde-2‘-deoxycytidine, using the standard methodology and site-specifically incorporated in both 15- and 25-mer oligonucleotides, for studies on biochemical and biophysical properties. The resulting oligonucleotides were purified using HPLC, and the base composition was verified by HPLC after enzymatic digestion.Keywords
This publication has 2 references indexed in Scilit:
- Hydrolysis of bisphenol A diglycidylether by epoxide hydrolases in cytosolic and microsomal fractions of mouse liver and skin: inhibition by bis epoxycyclopentylether and the effects upon the covalent binding to mouse skin DNACarcinogenesis: Integrative Cancer Research, 1989
- Synthesis of 6-amino-1-hexyl 2-acetamido-2-deoxy-3-, -4-, and -6-O-β-D-galactopyranosyl-β-D-glucopyranosidesCarbohydrate Research, 1980