N1630

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

Name: β-Nicotinamide adenine dinucleotide 2′-phosphate reduced tetrasodium salt hydrate
Brand: SIGMA

≥93% (HPLC)

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

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About This Item

Empirical Formula (Hill Notation):

C₂₁H₂₆N₇Na₄O₁₇P₃ · xH₂O

CAS Number:

2646-71-1

Molecular Weight:

833.35 (anhydrous basis)

NACRES:

NA.51

PubChem Substance ID:

24897509

UNSPSC Code:

41106305

EC Number:

220-163-3

MDL number:

MFCD00036263

Product Name

β-Nicotinamide adenine dinucleotide 2′-phosphate reduced tetrasodium salt hydrate, ≥93% (HPLC)

InChI key

WYWWVJHQDVCHKF-MPUNMZHWSA-J

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

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

biological source

chicken

assay

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

form

powder

solubility

10 mM NaOH: soluble 50 mg/mL, clear

storage temp.

−20°C

Quality Level

300

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Related Categories

Biochemicals

Nucleosides and Nucleotides

Phosphates

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.

Other Notes

Packaged based on solid weight.

Preparation Note

Chemically reduced.

Storage Class

11 - Combustible Solids

wgk

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Comparative analysis of NADPH-diaphorase positive neurons in the rat, rabbit and pheasant thoracic spinal cord. A histochemical study.

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.

In vitro ferredoxin-dependent desaturation of fatty acids in cyanobacterial thylakoid membranes.

H Wada et al.

Journal of bacteriology, 175(2), 544-547 (1993-01-01)

Thylakoid membranes isolated from the cyanobacterium Synechocystis sp. strain PCC6803 were capable of desaturating the acyl groups in monogalactosyl diacylglycerol. This desaturation reaction required the reduced form of ferredoxin.

Berg, J.M., et al.

Biochemistry (5th Edition) (2002)

William B. Wood

Biochemistry: A Problems Approach, 195-195 null

The desA gene of the cyanobacterium Synechocystis sp. strain PCC6803 is the structural gene for delta 12 desaturase.

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.

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