US EPA

7458558 

Journal Article 

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

Yagi, Y; Yamada, T; Nakatani, K 

2020 

Yes 

Biochemistry
ISSN: 0006-2960
EISSN: 1520-4995 

American Chemical Society 

59 

29 

2679-2683 

English 

10.1021/acs.biochem.0c00333 

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. Copyright © 2020 American Chemical Society. 

Alkylation; Osmium compounds; Chemical probing; Osmium tetroxide; Amines; 2,2' bipyridine; 5 methylcytosine; dimer; naphthyridine carbamate dimer; osmium tetraoxide; thymine; unclassified drug; 5 methylcytosine; naphthyridine derivative; thymine; Article; binding site; CGG repeat; deamination; DNA sequence; high performance liquid chromatography; matrix assisted laser desorption ionization time of flight mass spectrometry; oxidation; polyacrylamide gel electrophoresis; priority journal; reversed phase high performance liquid chromatography; synthesis; TGG sequence; trinucleotide repeat; chemistry; deamination; methylation; trinucleotide repeat; 2,2'-Dipyridyl; 5-Methylcytosine; Deamination; Methylation; Naphthyridines; Thymine; Trinucleotide Repeat Expansion; Trinucleotide Repeats