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2-Aminopurine

2-Aminopurine (2AP), a purine analog of guanine and adenine, is a fluorescent molecular marker used in nucleic acid research. 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.

It can also pair with cytosine at low pH in a protonated way like a functional analogue of guanine. For this reason it is sometimes used in the laboratory for mutagenesis. A mixture of structures are present according to NMR. An atomic-resolution structures of the 2AP·C pair has been produced.

References

References

  1. (2001). "2-Aminopurine fluorescence quenching and lifetimes: role of base stacking". Proc. Natl. Acad. Sci. U.S.A..
  2. (2009). "Biophysical, Chemical, and Functional Probes of RNA Structure, Interactions and Folding: Part B".
  3. (18 September 2020). "Predictions and analyses of RNA nearest neighbor parameters for modified nucleotides.". Nucleic Acids Research.
  4. (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..
  5. (27 June 2000). "Multiple structures for the 2-aminopurine-cytosine mispair.". Biochemistry.
  6. (22 November 2011). "Structure of the 2-aminopurine-cytosine base pair formed in the polymerase active site of the RB69 Y567A-DNA polymerase.". Biochemistry.
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