2-Aminopurine

2-Aminopurine, a purine analog of guanine and adenine, is a fluorescent molecular marker used in nucleic acid research.^[1] It most commonly pairs with thymine as an adenine-analogue, but can also pair with cytosine as a guanine-analogue.^[2] For this reason it is sometimes used in the laboratory for mutagenesis.

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

See also

• Nucleic acid analogues

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.