N-Sulfomethylation of guanine, adenine and cytosine with formaldehyde-bisulfite. A selective modification of guanine in DNA.
When guanine-, adenine- and cytosine-nucleosides and nucleotides were treated with formaldehyde and then with bisulfite, stable N-sulfomethyl compounds were formed. N2-Sulfomethylguanine, N6-sulfomethyladenine, N4-sulfomthylcytosine and N6-sulfomethyl-9-beta-D-arabinofuranosyladenine were isolated as crystals and characterized. A guanine-specific sulfomethylation was brought about by treatment and denatured single-stranded DNA with formaldehyde and then with bisulfite at pH 7 and 4 degrees C. Since native double-stranded DNA was not modified by this treatment, this new method of modification is expected to be useful as a conformational probe for polynucleotides.
D000225:Adenine; D003596:Cytosine; D004247:DNA; D005557:Formaldehyde; D006147:Guanine; D008745:Methylation; D008968:Molecular Conformation; D009705:Nucleosides; D009711:Nucleotides; D013329:Structure-Activity Relationship; D013447:Sulfites
D009705:Nucleosides; D009711:Nucleotides; D013447:Sulfites; D005557:Formaldehyde; D006147:Guanine; D003596:Cytosine; D004247:DNA; D000225:Adenine; C009279:sodium bisulfite