title: Synthesis and reaction of DNA oligomers containing modified cytosines related to bisulfite sequencing.
abstract: The synthesis of DNA oligomers containing N(4)-hydroxy-5,6-dihydrocytosine-6-sulfonate by using ligand-induced base flipping of cytosine followed by the simultaneous addition of bisulfite and hydroxylamine is reported. In contrast to C, the flipped-out 5-methylcytosine was selectively oxidized over thymines and cytosines in the duplex by potassium permanganate. Ligand-induced base flipping is a convenient and powerful strategy for the synthesis of modified cytosines and 5-methylcytosines related to bisulfite sequencing at the predetermined site of DNA.
authors.affiliation: Institute of Scientific and Industrial Research, Osaka University, 8-1 Mihogaoka, Ibaraki, Osaka 567-0047, Japan.
authors.forename: Yoshimi
authors.initials: Y
authors.lastname: Oka
authors.forename: Tao
authors.initials: T
authors.lastname: Peng
authors.forename: Fumie
authors.initials: F
authors.lastname: Takei
authors.forename: Kazuhiko
authors.initials: K
authors.lastname: Nakatani
mesh_terms: D002384:Catalysis; D003596:Cytosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D004247:DNA / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009841:Oligonucleotides / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: C539670:N4-hydroxy-5,6-dihydrocytosine-6-sulfonate; D009841:Oligonucleotides; D003596:Cytosine; D004247:DNA