2-Aminopurine

changed changed 477212531 2-Aminopurine correct ?? 2-Aminopurine.svg 230px 2-Aminopurine 9H-Purin-2-amine 1/C5H5N5/c6-5-7-1-3-4(10-5)9-2-8-3/h1-2H,(H3,6,7,8,9,10) MWBWWFOAEOYUST-UHFFFAOYAC correct EBI 388594 correct chemspider 1S/C5H5N5/c6-5-7-1-3-4(10-5)9-2-8-3/h1-2H,(H3,6,7,8,9,10) correct chemspider MWBWWFOAEOYUST-UHFFFAOYSA-N correct CAS 452-06-2 correct FDA O14B3U97FW 9955 correct chemspider 9561 correct EBI 479072 Nc2ncc1nc[nH]c1n2 5 5 5 2-Aminopurine (2AP), a purine analog of guanine and adenine, is a fluorescent molecular marker used in nucleic acid research.Jean JM, Hall KB 2-Aminopurine fluorescence quenching and lifetimes: role of base stacking Proc. Natl. Acad. Sci. U.S.A. 98 1 37–41 2001 11120885 10.1073/pnas.011442198 14540 free Hall Kathleen B. Biophysical, Chemical, and Functional Probes of RNA Structure, Interactions and Folding: Part B 2-Aminopurine as a Probe of RNA Conformational Transitions Methods in Enzymology 2009 469 269–285 10.1016/S0076-6879(09)69013-3 20946794 978-0-12-380922-3 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.Hopfinger MC Kirkpatrick CC Znosko BM Predictions and analyses of RNA nearest neighbor parameters for modified nucleotides. Nucleic Acids Research 18 September 2020 48 16 8901–8913 10.1093/nar/gkaa654 32810273 7498315 It can also pair with cytosine at low pH in a protonated way like a functional analogue of guanine.Sowers LC, Fazakerley GV, Eritja R, Kaplan BE, Goodman MF 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 5434–5438 1986 10.1073/pnas.83.15.5434 3461441 15 386301 1986PNAS...83.5434S free For this reason it is sometimes used in the laboratory for mutagenesis. A mixture of structures are present according to NMR.Sowers LC Boulard Y Fazakerley GV Multiple structures for the 2-aminopurine-cytosine mispair. Biochemistry 27 June 2000 39 25 7613–20 10.1021/bi992388k 10858312 An atomic-resolution structures of the 2AP·C pair has been produced.Reha-Krantz LJ Hariharan C Subuddhi U Xia S Zhao C Beckman J Christian T Konigsberg W Structure of the 2-aminopurine-cytosine base pair formed in the polymerase active site of the RB69 Y567A-DNA polymerase. Biochemistry 22 November 2011 50 46 10136–49 10.1021/bi2014618 22023103 3228362 See also Nucleic acid analogues References Category:Nucleobases Category:Purines