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N6005

Sigma-Aldrich

β-Nicotinamide adenine dinucleotide, reduced disodium salt hydrate

≥94% (HPLC)

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Synonym(s):
β-DPNH, β-NADH, DPNH, Diphosphopyridine nucleotide, reduced form, NADH
Empirical Formula (Hill Notation):
C21H27N7Na2O14P2 · xH2O
CAS Number:
Molecular Weight:
709.40 (anhydrous basis)
MDL number:
PubChem Substance ID:
NACRES:
NA.51

Quality Level

assay

≥94% (HPLC)
≥94% (spectrophotometric assay)

form

powder

shipped in

wet ice

storage temp.

−20°C

SMILES string

O.[Na+].[Na+].NC(=O)C1=CN(C=CC1)[C@@H]2O[C@H](COP([O-])(=O)OP([O-])(=O)OC[C@H]3O[C@H]([C@H](O)[C@@H]3O)n4cnc5c(N)ncnc45)[C@@H](O)[C@H]2O

InChI

1S/C21H29N7O14P2.2Na.H2O/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(32)14(30)11(41-21)6-39-44(36,37)42-43(34,35)38-5-10-13(29)15(31)20(40-10)27-3-1-2-9(4-27)18(23)33;;;/h1,3-4,7-8,10-11,13-16,20-21,29-32H,2,5-6H2,(H2,23,33)(H,34,35)(H,36,37)(H2,22,24,25);;;1H2/q;2*+1;/p-2/t10-,11-,13-,14-,15-,16-,20-,21-;;;/m1.../s1

InChI key

FWBNCIFELNNJCX-UHOVGGJYSA-L

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Application

β-Nicotinamide adenine dinucleotide (NAD+) and β-Nicotinamide adenine dinucleotide, reduced (NADH) comprise a coenzyme redox pair (NAD+:NADH) involved in a wide range of enzyme catalyzed oxidation reduction reactions. In addition to its redox function, NAD+/NADH is a donor of ADP-ribose units in ADP-ribosylaton (ADP-ribosyltransferases; poly(ADP-ribose) polymerases ) reactions and a precursor of cyclic ADP-ribose (ADP-ribosyl cyclases).
As a reagent, NADH can be used in enzyme cycling assays to amplify detection of activity of biologically relevant enzymes or metabolites present in low concentrations.

Biochem/physiol Actions

NADH is a coenzyme that functions as a regenerating electron donor in catabolic processes including glycolysis, β-oxidation and the citric acid cycle (Krebs cycle, TCA cycle). It participates in cell signaling events as well, for example as a substrate for the poly (ADP-ribose) polymerases (PARPs) during the DNA damage response. The NAD+/NADH dependent sirtuins play key roles in stress responses during events involving energy metabolism, with implications in cancer biology, diabetes and neurodegenerative disease.
As a reagent, NADH can be used in enzyme cycling assays to amplify detection of activity of biologically relevant enzymes or metabolites present in low concentrations.

Packaging

Packaged by solid weight.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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