5-Aza-7-deazapurine

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5-Aza-7-deazapurine
5-aza-7-deazapurine.svg
Names
Preferred IUPAC name
Imidazo[1,2-a][1,3,5]triazine
Other names
5-Aza-7-deazapurine
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C5H4N4/c1-2-9-4-6-3-8-5(9)7-1/h1-4H checkY[pubchem]
    Key: OXISDMSERFAPRY-UHFFFAOYSA-N checkY[pubchem]
  • InChI=1S/C5H4N4/c1-2-9-4-6-3-8-5(9)7-1/h1-4H
    Key: OXISDMSERFAPRY-UHFFFAOYSA-N
  • C1=CN2C=NC=NC2=N1
Properties
C5H4N4
Molar mass 120.115 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

5-Aza-7-deazapurine or imidazo[1,2-a][1,3,5]triazine[1] is a heterocyclic aromatic organic compound that consists of a s-triazine ring fused to an imidazole ring. It is an isostere and isomer of purine. However, in 5-aza-7-deazapurine, N-9 of five-membered ring does not bond with hydrogen. So 5-aza-7-deazapurine derivatives must have an exocyclic substituent with a double bond to bind a sugar residue.[2] 5-Aza-7-deazapurine nucleosides may have an oxo, thioxo, or a imine group.

Notable derivatives of this molecule include 5-aza-7-deazaguanine,[2] which is a nucleobase of hachimoji DNA.

See also[edit]

References[edit]

  1. ^ Seela, Frank; Amberg, Stefan; Melenewski, Alexander; Rosemeyer, Helmut (20 August 2001). "5-Aza-7-deazaguanine DNA: Recognition and Strand Orientation of Oligonucleotides Incorporating Anomeric Imidazo[1,2-a]-1,3,5-triazine Nucleosides". Helvetica. 84 (7): 1996–2014. doi:10.1002/1522-2675(20010711)84:7<1996::AID-HLCA1996>3.0.CO;2-1.
  2. ^ a b Chu, Chung K. (2002). Recent Advances in Nucleosides: Chemistry and Chemotherapy. Elsevier Science. p. 505. ISBN 9780444509512.