title: Site-specific generation of deoxyribonolactone lesions in DNA oligonucleotides.
abstract: [reaction: see text] An efficient method for the site-specific generation of 2-deoxyribonolactone oxidative DNA damage lesions from a "photocaged" nucleoside analogue was developed. A nucleoside phosphoramidite bearing a C-1' nitrobenzyl cyanohydrin was prepared and incorporated into DNA oligonucleotides using automated DNA synthesis. The caged analogue, which was stable in aqueous solution, was converted to the 2-deoxyribonolactone lesion by UV irradiation. DNA containing the caged analogue and the deoxyribonolactone site were characterized by electrospray mass spectrometry (ES-MS).
authors.affiliation: Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208-3113, USA.
authors.forename: H J
authors.initials: HJ
authors.lastname: Lenox
authors.forename: C P
authors.initials: CP
authors.lastname: McCoy
authors.forename: T L
authors.initials: TL
authors.lastname: Sheppard
mesh_terms: D002851:Chromatography, High Pressure Liquid; D004247:DNA / Q000138:chemical synthesis* / Q000737:chemistry; D004249:DNA Damage; D009841:Oligonucleotides / Q000138:chemical synthesis* / Q000737:chemistry; D010084:Oxidation-Reduction; D021241:Spectrometry, Mass, Electrospray Ionization; D013379:Substrate Specificity; D013400:Sugar Acids / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D009841:Oligonucleotides; D013400:Sugar Acids; C056405:2,4,5-trihydroxypentanoic acid gamma-lactone; D004247:DNA