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Chemical Probing of Thymine in the TGG/CGG Triad to Explore the Deamination of 5‑Methylcytosine in the CGG Repeat

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journal contribution
posted on 09.07.2020, 12:04 by Yuki Yagi, Takeshi Yamada, Kazuhiko Nakatani
The methylation of cytosine in the full mutation of the expanded CGG repeat and subsequent deamination to thymine could be a measure of repeat instability. We report the synthesis of NCD-Bpy, which binds to the TGG/CGG site in the repeat hairpin. NCD-Bpy forces the thymine in the TGG/CGG site to flip out from the π-stack, recruits osmium tetroxide in the vicinity of the flipped-out T, and oxidizes the T. The piperidine-induced cleavage band successfully determined the position of the T in the expanded CGG repeat.