Photochemical deoxyribose C2' oxidation in 5-iodouracil-containing hexanucleotide.
To investigate photochemistry of 5-iodouracil (IU) in DNA, photoreaction of IU-containing oligonucleotides was examined. It was found that d(GCAIU G C) 2 undergoes selective photochemical C1' and C2' oxidation at the 5' side of IU residue to provide ribonolactone-containing hexamer 1 and erythrose-containing hexamer 2. Upon heating under alkaline conditions, erythrose-containing hexamer 2 was found to undergo retro aldol condensation to provide two fragments having glycolaldehyde termini.
Sugiyama
H
H
Department of Synthetic Chemistry, Faculty of Engineering, Kyoto University, Japan.
Yamaguchi
E
E
Yamashita
K
K
Fujimoto
K
K
Tsutsumi
Y
Y
Saito
I
I
D003855:Deoxyribose / Q000737:chemistry*; D009841:Oligonucleotides / Q000737:chemistry*; D010084:Oxidation-Reduction; D010777:Photochemistry; D014498:Uracil / Q000031:analogs & derivatives* / Q000737:chemistry
D009841:Oligonucleotides; D003855:Deoxyribose; D014498:Uracil; C048747:5-iodouracil