Site-specific generation of deoxyribonolactone lesions in DNA oligonucleotides.
[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).
Lenox
H J
HJ
Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208-3113, USA.
McCoy
C P
CP
Sheppard
T L
TL
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
D009841:Oligonucleotides; D013400:Sugar Acids; C056405:2,4,5-trihydroxypentanoic acid gamma-lactone; D004247:DNA