Site-specific photomodification of single-stranded DNA targets by arylazide and perfluoroarylazide derivatives of oligonucleotides.
Highly efficient site-specific photomodification of single-stranded DNA targets was achieved with oligonucleotide reagents bearing aromatic azido groups (R (R1 = p-azidotetrafluorobenzoyl, R2 = 2-nitro-5-azidobenzoyl, R3 = p-azidobenzoyl) at either the terminal phosphate or at the C5 position of deoxyuridine at the end or inside of the oligonucleotide chain. The extent of modification strongly depends on the reagent type. It does not exceed 5% in the case of the reagent with R3. It was 25%-50% and 60%-70% for the reagents with R2 and R1 depending on the target structure. The reagent with perfluoroarylazido group R1 appeared to be most efficient. The extent of covalent adduct formation amounts to 70% for all reagents bearing a perfluoroarylazine group at the end of the oligonucleotide chain, independently of whether it was attached to the 3'- or 5'-phosphate or to the C5 of deoxyuridine. The reagents with the reactive group within the chain provided fewer cross-links (50%-55%). The reagents with R1 and R2 were found to be sensitive to the nucleotide structure of the target. Guanine and cytosine residues were modified preferentially when adjacent to the R1 or R2 group of the reagent, respectively.
Levina
A S
AS
Institute of Bioorganic Chemistry, Siberian Division of the Russian Academy of Sciences, Novosibirsk, Russia.
Tabatadze
D R
DR
Dobrikov
M I
MI
Shishkin
G V
GV
Khalimskaya
L M
LM
Zarytova
V P
VP
D001386:Azides / Q000737:chemistry; D001665:Binding Sites; D003432:Cross-Linking Reagents / Q000737:chemistry; D004277:DNA, Single-Stranded / Q000737:chemistry* / Q000235:genetics; D009841:Oligonucleotides / Q000737:chemistry* / Q000235:genetics; D010777:Photochemistry; D013329:Structure-Activity Relationship
D001386:Azides; D003432:Cross-Linking Reagents; D004277:DNA, Single-Stranded; D009841:Oligonucleotides