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Interaction Between 3‐( p ‐Tolylamino)‐1,5‐azulenequinone and the Deoxyguanosine Residue in Various Oligonucleotides upon Photolysis ¶
Author(s) -
Ru Hwu Jih,
Tsai FuYuan,
Tsay ShwuChen,
Hsien Chuang Shih,
Su TzuRong,
Lin ShwuBin,
Lin WeiChen,
Hsieh ChiaLin,
Kan LouSing
Publication year - 2001
Publication title -
photochemistry and photobiology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.818
H-Index - 131
eISSN - 1751-1097
pISSN - 0031-8655
DOI - 10.1562/0031-8655(2001)0740686ibptaa2.0.co2
Subject(s) - photodissociation , deoxyguanosine , chemistry , oligonucleotide , residue (chemistry) , stereochemistry , photochemistry , dna , organic chemistry , biochemistry
Eight single‐stranded oligodeoxyribonucleotides 32 P‐labeled at the 5′‐end were synthesized; they were annealed with the complementary oligodeoxyribonucleotides to form the corresponding double‐stranded helices. These duplexes possessed standard Watson–Crick base pairs, locally perturbed sites of a base mismatch, or a bulge. Further, 5′– 32 P‐labeled oligodeoxyribonucleotides with a hairpin loop were also synthesized. Cleavage of these single‐ and double‐stranded oligodeoxyribonucleotides selectively at the deoxyguanosine residue was accomplished by use of 3‐( p ‐tolylamino)‐1,5‐azulenequinone 1 upon irradiation with 350 nm UV light. The single strands were cleaved more efficiently than the double‐helices. For the helices containing a deoxyguanosine residue at a bulge, at a hairpin loop or toward the end, the cleaving efficiency was increased. Computation results indicate that two possibilities exist for agent 1 to form two “Watson–Crick type” hydrogen bonds with guanine in single‐stranded oligodeoxyribonucleotides; yet, only one possibility exists in duplexes.