Journal
ORGANIC LETTERS
Volume 11, Issue 6, Pages 1377-1379Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol900195z
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- Japan Society for the Promotion of Science (JSPS) [18105006]
- Ministry of Education, Culture, Sports, Science and Technology
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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.
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