title: An unexpected deamination reaction after hydrolysis of the pyrimidine (6-4) pyrimidone photoproduct.
abstract: Pyrimidine (6-4) pyrimidone photoproduct (6-4PP), a common DNA photolesion formed under solar irradiation, was indicated to hydrolyze under strong basic conditions, breaking the N3-C4 bond at the 5'-thymine. The reanalysis of this reaction revealed that the resulting water adduct may not be stable as previously proposed; it readily undergoes an esterification reaction induced by the 5-OH group at 6-4PP to form a five-membered ring, eliminating a molecule of ammonia.
authors.affiliation: Department of Chemistry and Chemical Biology, Indiana University-Purdue University Indianapolis (IUPUI) , 402 North Blackford Street, Indianapolis, Indiana 46202, United States.
authors.forename: Gengjie
authors.initials: G
authors.lastname: Lin
authors.forename: Yajun
authors.initials: Y
authors.lastname: Jian
authors.forename: Hao
authors.initials: H
authors.lastname: Ouyang
authors.forename: Lei
authors.initials: L
authors.lastname: Li
mesh_terms: D004247:DNA / Q000737:chemistry; D003641:Deamination; D006868:Hydrolysis; D009682:Magnetic Resonance Spectroscopy; D011743:Pyrimidines / Q000737:chemistry*; D011744:Pyrimidinones / Q000737:chemistry*; D013941:Thymine / Q000737:chemistry
chemical_list: D011743:Pyrimidines; D011744:Pyrimidinones; D004247:DNA; C030986:pyrimidine; D013941:Thymine