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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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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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