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2-Aminopurine

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2-Aminopurine
2-Aminopurine
Names
Preferred IUPAC name 9H-Purin-2-amine
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.006.545 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C5H5N5/c6-5-7-1-3-4(10-5)9-2-8-3/h1-2H,(H3,6,7,8,9,10)Key: MWBWWFOAEOYUST-UHFFFAOYSA-N
  • InChI=1/C5H5N5/c6-5-7-1-3-4(10-5)9-2-8-3/h1-2H,(H3,6,7,8,9,10)Key: MWBWWFOAEOYUST-UHFFFAOYAC
SMILES
  • Nc2ncc1ncc1n2
Properties
Chemical formula C5H5N5
Molar mass 135.130 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

2-Aminopurine, a purine analog of guanine and adenine, is a fluorescent molecular marker used in nucleic acid research. It most commonly pairs with thymine as an adenine-analogue, but can also pair with cytosine as a guanine-analogue. For this reason it is sometimes used in the laboratory for mutagenesis.

See also

References

  1. Jean JM, Hall KB (2001). "2-Aminopurine fluorescence quenching and lifetimes: role of base stacking". Proc. Natl. Acad. Sci. U.S.A. 98 (1): 37–41. doi:10.1073/pnas.011442198. PMC 14540. PMID 11120885.
  2. Sowers LC, Fazakerley GV, Eritja R, Kaplan BE, Goodman MF (1986). "Base pairing and mutagenesis: observation of a protonated base pair between 2-aminopurine and cytosine in an oligonucleotide by proton NMR". Proc. Natl. Acad. Sci. U.S.A. 83 (15): 5434–5438. Bibcode:1986PNAS...83.5434S. doi:10.1073/pnas.83.15.5434. PMC 386301. PMID 3461441.
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