1-Methylcytosine

Chemical compound 1-Methylcytosine.svg skin-invert 4-Amino-1-methylpyrimidin-2(1H)-one correct chemspider 71474 correct kegg 1S/C5H7N3O/c1-8-3-2-4(6)7-5(8)9/h2-3H,1H3,(H2,6,7,9) HWPZZUQOWRWFDB-UHFFFAOYSA-N correct chemspider 1S/C5H7N3O/c1-8-3-2-4(6)7-5(8)9/h2-3H,1H3,(H2,6,7,9) correct chemspider HWPZZUQOWRWFDB-UHFFFAOYSA-N correct CAS 1122-47-0 79143 correct FDA 1J54NE82RV correct EBI 39624 500883 CN1C=CC(=NC1=O)N 1-Methylcytosine 5 7 3 1 1-Methylcytosine (1mC) is a methylated form of the nucleic acid base cytosine. The deoxyribonucleoside it forms is called N1-methyl-2'-deoxy-pseudocytidine (m1ΨdC). In 1-methylcytosine, a methyl group is attached to the 1st atom in the 6-atom ring. This methyl group distinguishes 1-methylcytosine from cytosine. The location distinguishes it from the more (naturally) common 5-methylcytosine. 1mC forms hydrogen bonds differently compared to cytosine because it attaches to the backbone sugar (ribose or deoxyribose) differently: at the C5 position as opposed to cytidine's C1 position, analogous to the difference between pseudouridine and uridine. It pairs with isoguanine in Artificially Expanded Genetic Information System (hachimoji) DNA, replacing the unstable deoxyribonucleoside form of isocytosine.Hoshika Shuichi etal 22 February 2019 Hachimoji DNA and RNA: A genetic system with eight building blocks Science 363 6429 884–887 10.1126/science.aat0971 30792304 6413494 2019Sci...363..884H History Miriam Rossi worked on the refinement of the crystallographic structure of 1-methylcytosine.Kistenmacher T. J. Rossi M. 1977-12-15 1-Methylcytosine: a refinement Acta Crystallographica Section B 33 12 3962–3965 10.1107/S0567740877012618 1977AcCrB..33.3962R 0567-7408 It was discovered as a stable replacement for 2'-deoxy-5-methylisocytidine in 2009.Kim HJ Leal NA Benner SA 2'-deoxy-1-methylpseudocytidine, a stable analog of 2'-deoxy-5-methylisocytidine. Bioorganic & Medicinal Chemistry 15 May 2009 17 10 3728–32 10.1016/j.bmc.2009.03.047 19394831 5972679 References Category:Nucleobases Category:Pyrimidones