1-Methylcytosine

Chemical compound
1-Methylcytosine
Names
Preferred IUPAC name
4-Amino-1-methylpyrimidin-2(1H)-one
Identifiers
CAS Number
  • 1122-47-0 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:39624 checkY
ChEMBL
  • ChEMBL500883
ChemSpider
  • 71474 checkY
MeSH 1-Methylcytosine
PubChem CID
  • 79143
UNII
  • 1J54NE82RV checkY
CompTox Dashboard (EPA)
  • DTXSID60149949 Edit this at Wikidata
InChI
  • InChI=1S/C5H7N3O/c1-8-3-2-4(6)7-5(8)9/h2-3H,1H3,(H2,6,7,9) checkY
    Key: HWPZZUQOWRWFDB-UHFFFAOYSA-N checkY
  • InChI=1S/C5H7N3O/c1-8-3-2-4(6)7-5(8)9/h2-3H,1H3,(H2,6,7,9)
    Key: HWPZZUQOWRWFDB-UHFFFAOYSA-N
  • CN1C=CC(=NC1=O)N
Properties
Chemical formula
 C5H7N3O
Molar mass 125.131 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Chemical compound

1-Methylcytosine is a methylated form of the DNA base cytosine.

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.

History

Miriam Rossi worked on the refinement of 1-methylcytosine.[1]

1-Methylcytosine is used as a nucleobase of hachimoji DNA, in which it pairs with isoguanine.[2]

References

  1. ^ Kistenmacher, T. J.; Rossi, M. (1977-12-15). "1-Methylcytosine: a refinement". Acta Crystallographica Section B. 33 (12): 3962–3965. Bibcode:1977AcCrB..33.3962R. doi:10.1107/S0567740877012618. ISSN 0567-7408.
  2. ^ Hoshika, Shuichi; et al. (22 February 2019). "Hachimoji DNA and RNA: A genetic system with eight building blocks". Science. 363 (6429): 884–887. Bibcode:2019Sci...363..884H. doi:10.1126/science.aat0971. PMC 6413494. PMID 30792304.