2-aminopurine
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| Surname | 2-aminopurine | ||||||||||||||||||
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| Molecular formula | C 5 H 5 N 5 | ||||||||||||||||||
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| Molar mass | 135.13 g mol −1 | ||||||||||||||||||
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firmly |
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| Melting point |
280-282 ° C |
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| As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . | |||||||||||||||||||
2-aminopurine (also isoadenine ) is an isomer of the nucleobase adenine . It is a heterocyclic organic compound with a purine backbone and an amino group at position 2.
properties
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| Adenine, A. | 2-aminopurine ( isoadenine ) |
2-aminopurine is most likely to pair with thymine as an adenine analog, but also with cytosine as a guanine analog. It is therefore occasionally used as an experimental mutagen .
use
2-aminopurine has been used as a fluorescent marker in nucleic acid research since around 1990. The fluorescence of 2-aminopurine (2AP) was considered simple until 2014, but 2AP requires water for this. The fluorescence also differs depending on the binding site with water. This means that 2AP markers used in the investigation of DNA and RNA cannot be used as reliably as assumed until 2014. This requires the review of previous research results on fluorescence samples. 2AP has three docking points for water that influence the 2AP fluorescence behavior: If a water molecule is docked on one side of the 2AP, it glows weakly when exposed to UV radiation. At a second point, docking increases the fluorescence 50-fold, while at the third point a single water molecule increases the luminosity almost a hundredfold. The use of 2AP as a fluorescence sample is not in question, but the interpretation of the investigations. In “water-poor” surroundings, in RNA enzymes or DNA-enzyme complexes, one must differentiate between the “strong” and “weak” fluorescence side of 2AP. The environment around molecules changes their behavior.
literature
- André Dallmann, Lars Dehmel, Torben Peters, Clemens Mügge, Christian Griesinger, Jennifer Tuma, Nikolaus P. Ernsting: "The incorporation of 2-aminopurine influences the dynamics and structure of DNA", in: Angewandte Chemie , 2010 , 122 (34) , Pp. 6126-6129 ( doi : 10.1002 / anie.201001312 ).
Individual evidence
- ↑ a b c data sheet 2-Aminopurine ≥99% from Sigma-Aldrich , accessed on March 11, 2011 ( PDF ).
- ↑ LC Sowers, GV Fazakerley, R. Eritja, BE Kaplan, MF Goodman: "Base pairing and mutagenesis: observation of a protonated base pair between 2-aminopurine and cytosine in an oligonucleotide by proton NMR", in: Proc. Natl. Acad. Sci. USA , 1986 , 83 (15), pp. 5434-5438 ( doi : 10.1073 / pnas.83.15.5434 ; PMC 386301 (free full text); PMID 3461441 ).
- ↑ Marcus Menger: 2-aminopurine as a fluorescence indicator for the analysis of the structure and dynamics of oligoribonucleic acids and hammerhead ribozymes , dissertation, Göttingen 1999 ( PDF ).
- ↑ JM Jean, KB Hall: "2-Aminopurine fluorescence quenching and lifetimes: role of base stacking", in: Proc. Natl. Acad. Sci. USA , 2001 , 98 (1), pp. 37-41 ( doi : 10.1073 / pnas.011442198 ; PMC 14540 (free full text); PMID 11120885 ).
- ↑ Simon Lobsiger, Susan Blaser, Rajeev K. Sinha, Hans-Martin Frey, Samuel Leutwyler: "Switching on the Fluorescence of 2-Aminopurine by Site-Selective Microhydration", in: Nature Chemistry , October 2014 ( doi : 10.1038 / nchem. 2086 ).