title: Photochemical deoxyribose C2' oxidation in 5-iodouracil-containing hexanucleotide.
abstract: 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.
authors.affiliation: Department of Synthetic Chemistry, Faculty of Engineering, Kyoto University, Japan.
authors.forename: H
authors.initials: H
authors.lastname: Sugiyama
authors.forename: E
authors.initials: E
authors.lastname: Yamaguchi
authors.forename: K
authors.initials: K
authors.lastname: Yamashita
authors.forename: K
authors.initials: K
authors.lastname: Fujimoto
authors.forename: Y
authors.initials: Y
authors.lastname: Tsutsumi
authors.forename: I
authors.initials: I
authors.lastname: Saito
mesh_terms: D003855:Deoxyribose / Q000737:chemistry*; D009841:Oligonucleotides / Q000737:chemistry*; D010084:Oxidation-Reduction; D010777:Photochemistry; D014498:Uracil / Q000031:analogs & derivatives* / Q000737:chemistry
chemical_list: D009841:Oligonucleotides; D003855:Deoxyribose; D014498:Uracil; C048747:5-iodouracil