2-Aminopurine

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

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]

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]

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. Hall, Kathleen B. (2009). "2-Aminopurine as a Probe of RNA Conformational Transitions". Biophysical, Chemical, and Functional Probes of RNA Structure, Interactions and Folding: Part B. Methods in Enzymology. Vol. 469. pp. 269–285. doi:10.1016/S0076-6879(09)69013-3. ISBN   978-0-12-380922-3. PMID   20946794.
3. Hopfinger, MC; Kirkpatrick, CC; Znosko, BM (18 September 2020). "Predictions and analyses of RNA nearest neighbor parameters for modified nucleotides". Nucleic Acids Research. 48 (16): 8901–8913. doi:10.1093/nar/gkaa654. PMC   7498315 . PMID   32810273.
4. 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.
5. Sowers, LC; Boulard, Y; Fazakerley, GV (27 June 2000). "Multiple structures for the 2-aminopurine-cytosine mispair". Biochemistry. 39 (25): 7613–20. doi:10.1021/bi992388k. PMID   10858312.
6. Reha-Krantz, LJ; Hariharan, C; Subuddhi, U; Xia, S; Zhao, C; Beckman, J; Christian, T; Konigsberg, W (22 November 2011). "Structure of the 2-aminopurine-cytosine base pair formed in the polymerase active site of the RB69 Y567A-DNA polymerase". Biochemistry. 50 (46): 10136–49. doi:10.1021/bi2014618. PMC   3228362 . PMID   22023103.