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2-Aminopurine

Chemical compound From Wikipedia, the free encyclopedia

2-Aminopurine (2AP), a purine analog of guanine and adenine, is a fluorescent molecular marker used in nucleic acid research.[1][2] It most commonly pairs with thymine as an adenine-analogue. It uses a different ketone oxygen on thymine for H-bonding and forms a stronger bond.[3]

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2-Aminopurine
2-Aminopurine
2-Aminopurine
Names
Preferred IUPAC name
9H-Purin-2-amine
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.006.545 Edit this at Wikidata
UNII
  • InChI=1S/C5H5N5/c6-5-7-1-3-4(10-5)9-2-8-3/h1-2H,(H3,6,7,8,9,10) checkY
    Key: MWBWWFOAEOYUST-UHFFFAOYSA-N checkY
  • 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
  • Nc2ncc1nc[nH]c1n2
Properties
C5H5N5
Molar mass 135.130 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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It can also pair with cytosine at low pH in a protonated way like a functional analogue of guanine.[4] For this reason it is sometimes used in the laboratory for mutagenesis. A mixture of structures are present according to NMR.[5] An atomic-resolution structures of the 2AP·C pair has been produced.[6]

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