Chemical carcinogens in non-enzymatic cytosine deamination: 3-isocyanatoacrylonitrile
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Chemical carcinogens in non-enzymatic cytosine deamination: 3-isocyanatoacrylonitrile
Uracil has long been known as the main product of nitrosative cytosine deamination in aqueous solution. Recent mechanistic studies of cytosinediazonium ion suggest that the cation formed by its dediazoniation can ring-open to N-protonated (Z,s-cis)-3-isocyanatoacrylonitrile 7. Stereochemical preferences are discussed of the 3-isocyanatoacrylonitriles (Z,s-cis)-10, (E,s-cis)-11, (Z,s-trans)-12, ...
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A discussion of nitrosative deamination of cytosine 1 is presented that argues for the formation of 6 by diazotization of 1 to cytosinediazonium ion 2 and its electrostatic complex 3, dediazoniation to 4 <--> 5, and amide-bond cleavage to 6. The reaction channels available to 6 include hydrolytic deglycation to 3-isocyanatoacrylonitrile 7, water addition to carbamic acid 9 with the possibility ...
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ژورنال
عنوان ژورنال: Journal of Molecular Modeling
سال: 2006
ISSN: 1610-2940,0948-5023
DOI: 10.1007/s00894-005-0048-0