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Merck
CN

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:
452-06-2
Molecular Weight:
135.13
MDL number:
MFCD00005566
UNSPSC Code:
12352200

Key Documents

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Assay

≥97% (HPLC)

Quality Level

200

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.

Biochem/physiol Actions

Cell permeable: yes
Primary Target
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.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Disclaimer

Toxicity: Harmful (C)

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

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

新产品
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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
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
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
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

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