5.31619
2-Aminopurine
Synonym(s):
2-Aminopurine, 2-AP, 2AP
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About This Item
Empirical Formula (Hill Notation):
C5H5N5
CAS Number:
Molecular Weight:
135.13
MDL number:
UNSPSC Code:
12352200
Assay
≥97% (HPLC)
Quality Level
form
powder
manufacturer/tradename
Calbiochem®
storage condition
OK to freeze
protect from light
color
yellow
solubility
DMSO: 50 mg/mL
fluorescence
λex 303 nm
λem 370 nm
storage temp.
2-8°C
InChI
1S/C5H5N5/c6-5-7-1-3-4(10-5)9-2-8-3/h1-2H,(H3,6,7,8,9,10)
InChI key
MWBWWFOAEOYUST-UHFFFAOYSA-N
General description
A cell permeable adenine analog that is widely used as a versatile fluorescent probe to investigate RNA and DNA secondary and tertiary structures and their conformation dynamics in response to local environment when interacting with other biomolecules with great sensitivity. Forms stable base pairs with neucleobase uracil found in RNA and thymine in DNA, and moderately stable base pairs with cytosine. Exhibits intensive fluorescence emission (lAbsmax = 303 nM, lflmax = 370 nM, and fluorescence quantum yield in solution QFI = 0.68) and longer excitation wavelength compared with other neucleobases enabling its selective excitation with low background signals.
Please note that the molecular weight for this compound is batch-specific due to variable water content.
Please note that the molecular weight for this compound is batch-specific due to variable water content.
Biochem/physiol Actions
Cell permeable: yes
Primary Target
DNA and RNA
DNA and RNA
Reversible: yes
Packaging
Packaged under inert gas
Preparation Note
Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.
Other Notes
Ma, L., et al. 2014. Biochem. Biophys. Res. Comm.449, 120.
Widom, J. R., et al. 2013. New. J. Phys.15, 025028.
Souliere, M. F., et al. 2011. J. Am. Chem. Soc.133, 16161,
Jean, J. M., et al. 2001. PNAS98,37.
Widom, J. R., et al. 2013. New. J. Phys.15, 025028.
Souliere, M. F., et al. 2011. J. Am. Chem. Soc.133, 16161,
Jean, J. M., et al. 2001. PNAS98,37.
Legal Information
CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany
Disclaimer
Toxicity: Harmful (C)
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Acute Tox. 4 Oral
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Regulatory Information
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J M Jean et al.
Proceedings of the National Academy of Sciences of the United States of America, 98(1), 37-41 (2000-12-20)
2-Aminopurine (2AP) is a fluorescent analog of guanosine and adenosine and has been used to probe nucleic acid structure and dynamics. Its spectral features in nucleic acids have been interpreted phenomenologically, in the absence of a rigorous electronic description of
Julia R Widom et al.
New journal of physics, 15 (2013-11-14)
We have observed the conformation-dependent electronic coupling between the monomeric subunits of a dinucleotide of 2-aminopurine (2-AP), a fluorescent analog of the nucleic acid base adenine. This was accomplished by extending two-dimensional fluorescence spectroscopy (2D FS) - a fluorescence-detected variation
Marie F Soulière et al.
Journal of the American Chemical Society, 133(40), 16161-16167 (2011-09-03)
A precise tertiary structure must be adopted to allow the function of many RNAs in cells. Accordingly, increasing resources have been devoted to the elucidation of RNA structures and the folding of RNAs. 2-Aminopurine (2AP), a fluorescent nucleobase analogue, can
Long Ma et al.
Biochemical and biophysical research communications, 449(1), 120-125 (2014-05-13)
EcoP15I is a Type III DNA restriction and modification enzyme of Escherichia coli. We show that it contains two modification (Mod) subunits for sequence-specific methylation of DNA and one copy of a restriction endonuclease (Res) subunit for cleavage of DNA
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