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Chemical methods for decoding cytosine modifications in DNA.

Booth MJ, Raiber EA, Balasubramanian S - Chem. Rev. (2014)

View Article: PubMed Central - PubMed

Affiliation: †Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, CB2 1EW United Kingdom.

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and therefore does not introduce a strand cleavage... This results in hydroysis with loss of ammonia... The resulting uracil bisulfite adduct also decreases at pH values below 5.0 due to the protonation of the most effective catalytic species, sulphite... with 5mC than with C, due to inhibition of the adduct formation from the electronic effect of the methyl group... buffers”; however, there has been no definitive examination of their effectiveness... resolution map of 5mC, 5hmC and 5fCs... 5hmC and, through oxidiation of 5mC with the TET enzymes, have been might be feasible to use such nanopores to discriminate 5mC and 5hmC By chemically altering the primary alcohol of 5hmC it is It is now possible to decode 5mC, 5hmC,

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Mechanism of sodium bisulfite deamination of cytosineto uracilthrough the addition of sodium bisulfite across the C5–6 doublebond of C, followed by deamination of the cytosine bisulfite adduct.The uracil bisulfite adduct can then be worked up using alkaline conditions.
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fig12: Mechanism of sodium bisulfite deamination of cytosineto uracilthrough the addition of sodium bisulfite across the C5–6 doublebond of C, followed by deamination of the cytosine bisulfite adduct.The uracil bisulfite adduct can then be worked up using alkaline conditions.

Mentions: The deamination reaction of C to U with bisulfitewas first observed in 1970.47 The bisulfiteanion adds across the C5–6 double bond of C at acidic pH, togenerate an adduct, which has lost aromaticity of the base and undergoeshydroysis with loss of ammonia. The resulting uracil bisulfite adductrearomatises to form uracil upon an increase in pH (Figure 12). This reaction requires the single stranded formof DNA (ssDNA), owing to the inaccessibility of the C5–6 doublebond to the bisulfite anion in the double helix.48


Chemical methods for decoding cytosine modifications in DNA.

Booth MJ, Raiber EA, Balasubramanian S - Chem. Rev. (2014)

Mechanism of sodium bisulfite deamination of cytosineto uracilthrough the addition of sodium bisulfite across the C5–6 doublebond of C, followed by deamination of the cytosine bisulfite adduct.The uracil bisulfite adduct can then be worked up using alkaline conditions.
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Related In: Results  -  Collection

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Show All Figures
getmorefigures.php?uid=PMC4378238&req=5

fig12: Mechanism of sodium bisulfite deamination of cytosineto uracilthrough the addition of sodium bisulfite across the C5–6 doublebond of C, followed by deamination of the cytosine bisulfite adduct.The uracil bisulfite adduct can then be worked up using alkaline conditions.
Mentions: The deamination reaction of C to U with bisulfitewas first observed in 1970.47 The bisulfiteanion adds across the C5–6 double bond of C at acidic pH, togenerate an adduct, which has lost aromaticity of the base and undergoeshydroysis with loss of ammonia. The resulting uracil bisulfite adductrearomatises to form uracil upon an increase in pH (Figure 12). This reaction requires the single stranded formof DNA (ssDNA), owing to the inaccessibility of the C5–6 doublebond to the bisulfite anion in the double helix.48

View Article: PubMed Central - PubMed

Affiliation: †Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, CB2 1EW United Kingdom.

AUTOMATICALLY GENERATED EXCERPT
Please rate it.

and therefore does not introduce a strand cleavage... This results in hydroysis with loss of ammonia... The resulting uracil bisulfite adduct also decreases at pH values below 5.0 due to the protonation of the most effective catalytic species, sulphite... with 5mC than with C, due to inhibition of the adduct formation from the electronic effect of the methyl group... buffers”; however, there has been no definitive examination of their effectiveness... resolution map of 5mC, 5hmC and 5fCs... 5hmC and, through oxidiation of 5mC with the TET enzymes, have been might be feasible to use such nanopores to discriminate 5mC and 5hmC By chemically altering the primary alcohol of 5hmC it is It is now possible to decode 5mC, 5hmC,

Show MeSH
Related in: MedlinePlus