A highly fluorescent analog of AMP
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1,N6-Ethenoadenosine 5'-monophosphate (sodium salt)

Item No. 21227

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3-(5-O-phosphono-β-D-ribofuranosyl)-3H-imidazo[2,1-i]purine, disodium salt
CAS Number
885597-18-2
Synonyms
  • 1,N6-ε-AMP
  • 1,N6-Etheno-AMP
Molecular Formula
C12H12N5O7P • 2Na
Formula Weight
415.2
Purity
≥97%
Emission
415 nm
Excitation
250-300 nm
Formulation (Request formulation change)
A lyophilized solid
Solubility(Learn about Variance in Solubility)
Water: Soluble
λmax
275 nm
SMILES
O[C@H]1[C@H](N2C=NC3=C2N=CN4C3=NC=C4)O[C@H](COP([O-])([O-])=O)[C@H]1O.[Na+].[Na+]
InChi Code
InChI=1S/C12H14N5O7P.2Na/c18-8-6(3-23-25(20,21)22)24-12(9(8)19)17-5-14-7-10-13-1-2-16(10)4-15-11(7)17;;/h1-2,4-6,8-9,12,18-19H,3H2,(H2,20,21,22);;/q;2*+1/p-2/t6-,8-,9-,12-;;/m1../s1
InChi Key
KVSQHHAQCKSCRL-CMUBXXRSSA-L
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    10 µmol

    $262

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    Product Description

    1,N6-Ethenoadenosine 5'-monophosphate (1,N6-ε-AMP) is a highly fluorescent analog of adenosine 5’-monophosphate (AMP; Item No. 21094).1,2 1,N6-ε-AMP is characterized by a long fluorescent lifetime, detectability at low concentration, a relatively long wavelength of excitation (250-300 nm), and emission at 415 nm.2,3,4 1,N6-ε-AMP can be used in assays of 5’-nucleotidase activity.5,6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Jahnz-Wechmann, Z., Framski, G.R., Januszczyk, P.A., et al. Base-modified nucleosides: Etheno derivatives. Front. Chem. 4, 19 (2016).

    2. Secrist, J.A., III, Barrio, J.R., Leonard, N.J., et al. Fluorescent modification of adenosine 3',5'-monophosphate: spectroscopic properties and activity in enzyme systems. Science 177(4045), 279-280 (1972).

    3. Penzer, G.R. The solution conformation and some spectroscopic properties of 1,N 6 -ethenoadenosine monophosphate, a fluorescent analogue of AMP. Eur. J. Biochem. 34(2), 297-305 (1973).

    4. Spencer, R.D., Weber, G., Tolman, G.L., et al. Species responsible for the fluorescence of 1:N6-ethenoadenosine. Eur. J. Biochem. 45(2), 425-429 (1974).

    5. Jamaz, Z., Afkham-Ebrahimi, A., and Saggerson, E.D. A novel assay for 5'-nucleotidase using 1,N6-etheno-AMP as substrate, and comments on the properties of the reaction product, ethenoadenosine. Biochem J. 250(2), 369-373 (1988).

    6. Pexa, A., and Deussen, A. Modulation of ecto-5'-nucleotidase by phospholipids in human umbilical vein endothelial cells (HUVEC). Naunyn-Schmiedeberg's Arch. Pharmacol. 372(2), 131-138 (2005).