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N1630

Sigma-Aldrich

β-Nicotinamide adenine dinucleotide 2′-phosphate reduced tetrasodium salt hydrate

≥93% (HPLC)

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Synonym(s):
β-NADPH, 2′-NADPH hydrate, Coenzyme II reduced tetrasodium salt, Dihydronicotinamide adenine dinucleotide phosphate tetrasodium salt, NADPH Na4, TPNH2 Na4, Triphosphopyridine nucleotide reduced tetrasodium salt
Empirical Formula (Hill Notation):
C21H26N7Na4O17P3 · xH2O
CAS Number:
2646-71-1
Molecular Weight:
833.35 (anhydrous basis)
EC Number:
220-163-3
MDL number:
MFCD00036263
PubChem Substance ID:
24897509
NACRES:
NA.51

Assay

≥93% (HPLC)
≥93% (spectrophotometric assay)

form

powder

solubility

10 mM NaOH: soluble 50 mg/mL, clear

storage temp.

−20°C

SMILES string

[Na+].[Na+].[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](OP([O-])([O-])=O)[C@@H]3O)n4cnc5c(N)ncnc45)[C@H](O)[C@@H]2O

InChI

1S/C21H30N7O17P3.4Na/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(44-46(33,34)35)14(30)11(43-21)6-41-48(38,39)45-47(36,37)40-5-10-13(29)15(31)20(42-10)27-3-1-2-9(4-27)18(23)32;;;;/h1,3-4,7-8,10-11,13-16,20-21,29-31H,2,5-6H2,(H2,23,32)(H,36,37)(H,38,39)(H2,22,24,25)(H2,33,34,35);;;;/q;4*+1/p-4/t10-,11+,13-,14+,15-,16+,20-,21+;;;;/m0..../s1

InChI key

WYWWVJHQDVCHKF-MPUNMZHWSA-J

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Application

β-NADPH is suitable for use in:
  • desaturation of fatty acids
  • an assay of desaturase activity
  • the histochemical detection of NADPH diaphorase activity in rat, rabbit and pheasant thoracic spinal cord
  • the measurement of glutathione in oligodendrocyte cultures

Biochem/physiol Actions

β-NADPH is the reduced form of NADP+ generated by the pentose phosphate pathway. It serves as a carrier of reducing power and transfers H+ and 2 e– to the oxidized precursors in the reduction reactions of biosynthesis. It is an essential coenzyme for the catalytic activity of enzymes such as glutathione reductase, diacetyl reductase, dihydrofolate reductase, glutamic dehydrogenase, p-hydroxybenzoate hydroxylase, NADPH-FMN oxidoreductase, nitrate reductase, and thioredoxin reductase. It is also a part of cytochrome P450 electron transport systems.
NADPH is an electron donor and a cofactor for many redox enzymes including nitric oxide synthetase.

Preparation Note

Chemically reduced.

Other Notes

Packaged based on solid weight.

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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H Wada et al.
Journal of bacteriology, 175(18), 6056-6058 (1993-09-01)
The desA gene of the cyanobacterium Synechocystis sp. strain PCC6803 was expressed in Escherichia coli, which does not contain any fatty acid desaturase. The product of the desA gene catalyzed the desaturation of fatty acids at the delta 12 position.
D Kluchová et al.
General physiology and biophysics, 21(2), 163-174 (2002-09-19)
The NADPH-diaphorase (NADPH-d) staining method is widely used in the investigation of both the central and peripheral nervous systems. Neuronal nitric oxide synthase (nNOS) has previously been shown to be responsible for the NADPH-d activity in neurons. However, NADPH-d activity
D Kluchová et al.
European journal of histochemistry : EJH, 45(3), 239-248 (2002-01-05)
The distribution of NADPH-diaphorase (NADPH-d) activity was investigated and compared in the rat, rabbit and pheasant thoracic spinal cord. The investigation of all spinal cord regions (laminae) in three experimental species revealed marked differences in the distribution of NADPH-d activity.
S A Back et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 18(16), 6241-6253 (1998-08-11)
Death of oligodendrocyte (OL) precursors can be triggered in vitro by cystine deprivation, a form of oxidative stress that involves depletion of intracellular glutathione. We report here that OLs demonstrate maturation-dependent differences in survival when subjected to free radical-mediated injury
D Kluchova et al.
European journal of histochemistry : EJH, 54(4), e47-e47 (2011-01-26)
In the current study, we aimed at investigating the presence of nitric oxide synthase (NOS) positive nerve fibers in rat meibomian glands (MGs) at various stages of development. There is good evidence to suggest that nicotinamide adenine dinucleotide phosphate diaphorase
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