5-Aza-7-deazapurine

Last updated
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
PubChem CID
  • InChI=1S/C5H4N4/c1-2-9-4-6-3-8-5(9)7-1/h1-4H Yes check.svgY[ pubchem ]
    Key: OXISDMSERFAPRY-UHFFFAOYSA-N Yes check.svgY[ 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

Related Research Articles

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Nucleotides are organic molecules composed of a nitrogenous base, a pentose sugar and a phosphate. They serve as monomeric units of the nucleic acid polymers – deoxyribonucleic acid (DNA) and ribonucleic acid (RNA), both of which are essential biomolecules within all life-forms on Earth. Nucleotides are obtained in the diet and are also synthesized from common nutrients by the liver.

<span class="mw-page-title-main">Purine</span> Heterocyclic aromatic organic compound

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<span class="mw-page-title-main">Nucleobase</span> Nitrogen-containing biological compounds that form nucleosides

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<span class="mw-page-title-main">Nucleoside</span> Any of several glycosylamines comprising a nucleobase and a sugar molecule

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<span class="mw-page-title-main">Ribonucleotide</span> Nucleotide containing ribose as its pentose component

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1,3,5-Triazine, also called s-triazine, is an organic chemical compound with the formula (HCN)3. It is a six-membered heterocyclic aromatic ring, one of several isomeric triazines. S-triazine—the "symmetric" isomer—and its derivatives are useful in a variety of applications.

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2,4,6-Tris(trinitromethyl)-1,3,5-triazine is a chemical compound that is a derivative of triazine first prepared in 1995. It is synthesized by destructive nitration of 2,4,6-tricarboxyl-1,3,5-triazine. It is noteworthy for having more nitro groups than it does carbon atoms, thus potentially being useful as an oxygen source, or added to oxygen-poor explosives to increase their power.

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<span class="mw-page-title-main">Hexahydro-1,3,5-triazine</span> Class of chemical compounds

In chemistry, hexahydro-1,3,5-triazine is a class of heterocyclic compounds with the formula (CH2NR)3. They are reduced derivatives of 1,3,5-triazine, which have the formula (CHN)3, a family of aromatic heterocycles. They are often called triazacyclohexanes or TACH's but this acronym is also applied to cis,cis-1,3,5-triaminocyclohexane.

<span class="mw-page-title-main">5-Aza-7-deazaguanine</span> Chemical compound

5-Aza-7-deazaguanine or 2-aminoimidazo[1,2-a][1,3,5]triazin-4(1H)-one is a 5-Aza-7-deazapurine base that is an isomer of guanine. It is used as a nucleobase of hachimoji DNA, in which it pairs with 6-Amino-5-nitropyridin-2-one.

References

  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. 1 2 Chu, Chung K. (2002). Recent Advances in Nucleosides: Chemistry and Chemotherapy. Elsevier Science. p. 505. ISBN   9780444509512.