Reaction of bisulfite with the 5-hydroxymethyl group in pyrimidines and in phage DNAs.
5-Hydroxymethylcytosine reacted with bisulfite and, instead of undergoing usual deamination process, gave cytosine 5-methylenesulfonate as the product. The conversion was rapid and quantitative, and the optimum pH was 4.5. The product was isolated as crystals and characterized. Cytosine 5-methylenesulfonate was only very slowly deaminated by treatment with bisulfite. 5-Hydroxymethyl-2'-deoxycytidine 5'-phosphate reacted with bisulfite in the same way as 5-hydroxymethylcytosine. Residues of 5-hydroxymethylcytosine in native as well as denatured T2 DNA were convertible to those of cytosine 5-methylenesulfonate by treatment of the DNA with bisulfite. While it is known that the 5-hydroxy-methyl groups of T-even bacteriophage DNA can be enzymatically glucosylated, this observation offers chemical evidence that the 5-hydrozymethyl groups in DNA are situated in such a way that they can readily react with external agents. 5-Hydroxymethyluracil gave uracil 5-methylenesulfonate on treatment with bisulfite. This reaction was much slower than that of 5-hydroxymethylcytosine, and the optimum pH was between 6 and 7.
D044503:5-Methylcytosine / Q000031:analogs & derivatives; D055598:Chemical Phenomena; D002621:Chemistry; D003090:Coliphages; D003596:Cytosine / Q000031:analogs & derivatives; D004279:DNA, Viral; D010432:Pentoxyl / Q000031:analogs & derivatives; D011743:Pyrimidines; D013056:Spectrophotometry, Ultraviolet; D013447:Sulfites; D014498:Uracil / Q000031:analogs & derivatives
D004279:DNA, Viral; D011743:Pyrimidines; D013447:Sulfites; C011865:5-hydroxymethylcytosine; C008055:5-hydroxymethyluracil; D014498:Uracil; D044503:5-Methylcytosine; D010432:Pentoxyl; D003596:Cytosine