2-Aminopurine

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]

2-Aminopurine

2-Aminopurine
Names
Preferred IUPAC name 9H-Purin-2-amine
Identifiers
CAS Number	452-06-2 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:479072 Y
ChEMBL	ChEMBL388594 Y
ChemSpider	9561 Y
ECHA InfoCard	100.006.545
PubChem CID	9955
UNII	O14B3U97FW Y
CompTox Dashboard (EPA)	DTXSID40196416
InChI InChI=1S/C5H5N5/c6-5-7-1-3-4(10-5)9-2-8-3/h1-2H,(H3,6,7,8,9,10) Y Key: MWBWWFOAEOYUST-UHFFFAOYSA-N Y 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 Nc2ncc1nc[nH]c1n2
Properties
Chemical formula	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). N verify (what is YN ?) Infobox references

It can also pair with cytosine at low pH in a protonated wya 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]

See also

• Nucleic acid analogues