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N6879

Sigma-Aldrich

α-Nicotinamide adenine dinucleotide, reduced disodium salt

≥90%

Synonym(s):

α-DPNH, α-Dihydrodiphosphopyridine nucleotide, α-Dihydronicotinamide adenine dinucleotide, α-NADH

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About This Item

Linear Formula:
C21H27N7O14P2Na2
CAS Number:
108321-31-9
Molecular Weight:
709.40
MDL number:
MFCD00079521
UNSPSC Code:
41106305
PubChem Substance ID:
24897797
NACRES:
NA.51

Assay

≥90%

form

powder

impurities

≤3% β-isomer

storage temp.

−20°C

SMILES string

[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/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);;/q;2*+1/p-2/t10-,11+,13-,14+,15-,16+,20+,21+;;/m1../s1

InChI key

QRGNQKGQENGQSE-WPVKCSLBSA-L

Application

α-Nicotinamide adenine dinucleotide, reduced (α-NADH) may be used as a cosubstrate to assess the specificity and kinetics of NAD+/NADH and NADP+/NADPH dependent enzymes and to assess the dynamics of nucleotides in ion channels such as voltage-dependent mitochondrial ion channels (VDAC).

Other Notes

Analog of β-NADH, chemically reduced

Caution

This is not the common NADH required in the usual enzyme systems.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Andrea Amaroli et al.
European journal of protistology, 42(3), 201-208 (2006-10-31)
Recently, we showed that Paramecium primaurelia synthesizes molecules functionally related to the cholinergic system and involved in modulating cell-cell interactions leading to the sexual process of conjugation. It is known that nitric oxide (NO) plays a role in regulating the
E S Kirkor et al.
European journal of biochemistry, 267(16), 5014-5022 (2000-08-10)
NADH chemistry ancillary to the oscillatory peroxidase-oxidase (PO) reaction has been reexamined. Previously, (NAD)2 has been thought of as a terminal, inert product of the PO reaction. We now show that (NAD)2 is a central reactant in this system. Although
Tatiana K Rostovtseva et al.
Biophysical journal, 82(1 Pt 1), 193-205 (2001-12-26)
Nucleotide penetration into the voltage-dependent mitochondrial ion channel (VDAC) reduces single-channel conductance and generates excess current noise through a fully open channel. VDAC channels were reconstituted into planar phospholipid membranes bathed in 1.0 M NaCl. At a given nucleotide concentration

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