On October 31, 1992, Kusmierek, J. T.; Singer, B. published an article.Quality Control of Imidazo[1,2-c]pyrimidin-5(6H)-one The title of the article was 1,N2-Ethenodeoxyguanosine: properties and formation in chloroacetaldehyde-treated polynucleotides and DNA. And the article contained the following:
1,N2-Etheno-2′-deoxyguanosine (1,N2-εdGuo) (I), not previously reported as a product of chloroacetaldehyde (CAA) reaction, was synthesized and characterized. Reaction of deoxyguanosine with CAA in DMF in the presence of K2CO3 led to the preparation of pure 1,N2-εdGuo with a 55% yield. PKa values are 2.2 and 9.2. The anionic form of the compound exhibits weak but defined fluorescence; the intensity is similar to that of N2,3-etheno-2′-deoxyguanosine (N2,3-εdGuo) at neutrality. The stability of the glycosyl bond of 1,N2-εdGuo (t1/2 = 2.3 h at 37°, pH 1) is 10-fold greater than of unmodified deoxyguanosine and at least 1000-fold greater than that of isomeric N2,3-εdGuo. Reaction of CAA with model polynucleotides indicates that hydrogen bonding of guanine residues in the double-stranded structures is, as expected, an important factor in the formation of 1,N2-ethenoguanine. In contrast, the formation of isomeric N2,3-ethenoguanine is relatively independent of whether the DNA is single- or double-stranded. In salmon sperm DNA, reacted with CAA at neutrality, the formation of 1,N2-ethenoguanine could be demonstrated. However, the authors find the efficiency of formation of this adduct in double-stranded DNA is lower than that of all other etheno derivatives The experimental process involved the reaction of Imidazo[1,2-c]pyrimidin-5(6H)-one(cas: 55662-66-3).Quality Control of Imidazo[1,2-c]pyrimidin-5(6H)-one
The Article related to chloroacetaldehyde ethenodeoxyguanosine polynucleotide dna, Toxicology: Carcinogens, Mutagens, and Teratogens and other aspects.Quality Control of Imidazo[1,2-c]pyrimidin-5(6H)-one
Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem