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]

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]

References

↑ "2-Aminopurine fluorescence quenching and lifetimes: role of base stacking". Proc. Natl. Acad. Sci. U.S.A. 98 (1): 37–41. 2001. doi:10.1073/pnas.011442198. PMID 11120885.
↑ 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. 469. pp. 269–285. doi:10.1016/S0076-6879(09)69013-3. ISBN 978-0-12-380922-3.
↑ 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. PMID 32810273.
↑ "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. 1986. doi:10.1073/pnas.83.15.5434. PMID 3461441. Bibcode: 1986PNAS...83.5434S.
↑ 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.
↑ 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. PMID 22023103.

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[1] "2-Aminopurine fluorescence quenching and lifetimes: role of base stacking". Proc. Natl. Acad. Sci. U.S.A. 98 (1): 37–41. 2001. doi:10.1073/pnas.011442198. 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. 469. pp. 269–285. doi:10.1016/S0076-6879(09)69013-3. ISBN 978-0-12-380922-3.

[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. PMID 32810273.

[4] "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. 1986. doi:10.1073/pnas.83.15.5434. PMID 3461441. Bibcode: 1986PNAS...83.5434S.

[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. PMID 22023103.

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2-Aminopurine

Topic: Chemistry

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References