The 5,6-double bond of pyrimidine nucleosides, a fragile site in nucleic acids.
Our studies have revealed reagents that can attack the 5,6-double bond of pyrimidine nucleosides; potassium permanganate and bisulfite. This review is a personal account of these studies, with a discussion on the vulnerable nature of this particular double bond to external nucleophiles and oxidizing agents. The finding that N(4)aminocytidine, produced on treatment of cytidine with bisulfite and hydrazine, is a strong mutagen is also described.
Hayatsu
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Faculty of Pharmaceutical Sciences, Okayama University.
D043283:Chromosome Fragile Sites; D002873:Chromosome Fragility; D003562:Cytidine / Q000031:analogs & derivatives; D006834:Hydrazines; D017895:Manganese Compounds; D009153:Mutagens; D009690:Nucleic Acid Conformation; D010087:Oxides; D011741:Pyrimidine Nucleosides / Q000737:chemistry*; D013447:Sulfites
D006834:Hydrazines; D017895:Manganese Compounds; D009153:Mutagens; D010087:Oxides; D011741:Pyrimidine Nucleosides; D013447:Sulfites; C048856:permanganic acid; C029424:hydrazine; C038769:N(4)-aminocytidine; D003562:Cytidine; C042345:hydrogen sulfite