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N2630

Sigma-Aldrich

Nicotinamide 1,N6-ethenoadenine dinucleotide

≥98%

Synonym(s):

ε-NAD, 1,N6-Etheno NAD, 1,N6-Ethenonicotinamide adenine dinucleotide

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About This Item

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

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

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
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
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
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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