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N2630

Sigma-Aldrich

Nicotinamide 1,N6-ethenoadenine dinucleotide

≥98%

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Synonym(s):
ε-NAD, 1,N6-Etheno NAD, 1,N6-Ethenonicotinamide adenine dinucleotide
Empirical Formula (Hill Notation):
C23H27N7O14P2
CAS Number:
38806-38-1
Molecular Weight:
687.45
MDL number:
MFCD00063546
UNSPSC Code:
41106305
PubChem Substance ID:
24897579
NACRES:
NA.51

Quality Level

200

assay

≥98%

form

powder

storage temp.

−20°C

SMILES string

NC(=O)C1=CC=C[N](=C1)C2OC(COP(O)(=O)OP(O)(=O)OCC3OC(C(O)C3O)n4cnc5c4ncn6ccnc56)C(O)C2O

InChI

1S/C23H28N7O14P2/c24-19(35)11-2-1-4-28(6-11)22-17(33)15(31)12(42-22)7-40-45(36,37)44-46(38,39)41-8-13-16(32)18(34)23(43-13)30-10-26-14-20-25-3-5-29(20)9-27-21(14)30/h1-6,9-10,12-13,15-18,22-23,31-34H,7-8H2,(H2,24,35)(H,36,37)(H,38,39)

InChI key

AVLUSNAXLARRGJ-UHFFFAOYSA-N

Application

Nicotinamide 1,N6-ethenoadenine dinucleotide (ε-NAD) is an NAD fluorescent analog (fluorophore) that may be used to study ADP-ribosylation reactions and the structure/kinetics of NAD+ binding enzymes by assays such as etheno-NAD+ assay.

Other Notes

Analog of β-NAD

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

wgk_germany

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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ADP-ribosylation and NAD+
Utilizing Enzymes
Paul Chang
Methods in Molecular Biology, 77-90 (2018)
Hélène Muller-Steffner et al.
ACS chemical biology, 12(7), 1787-1795 (2017-05-10)
SmNACE is a NAD catabolizing enzyme expressed on the outer tegument of S. mansoni, a human parasite that is one of the major agents of the neglected tropical disease schistosomiasis. Recently, we identified aroylhydrazone derivatives capable of inhibiting the recombinant
R Favilla et al.
Biochimica et biophysica acta, 788(1), 48-57 (1984-07-17)
The binding of 1,N6-etheno-NAD (epsilon NAD) to bovine liver glutamate dehydrogenase (L-glutamate:NAD(P)+ oxidoreductase (deaminating), EC 1.4.1.3) saturated with glutarate has been investigated at pH 7.0, 0.05 M phosphate buffer at 20 degrees C, by fluorescence titrations. epsilon NAD binds to
Hiroki Kawamura et al.
Journal of immunology (Baltimore, Md. : 1950), 174(4), 1971-1979 (2005-02-09)
Adding NAD to murine T lymphocytes inhibits their functions and induces annexin V binding. This report shows that NAD induces cell death in a subset of T cells within seconds whereas others do not die until many hours later. Low
L A Basso et al.
Biochimica et biophysica acta, 1340(1), 63-71 (1997-06-20)
The mechanism of the binding of reduced coenzyme (NAD+) to clostridial glutamate dehydrogenase (GDH) was determined by transient kinetics. The fluorescent 1,N6-ethenoadenine analogue of NAD+ (epsilonNAD+) was used as a probe of nucleotide binary and ternary complex formation because the
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