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ChemicalBook--->CAS DataBase List--->53-59-8

53-59-8

53-59-8 Structure

53-59-8 Structure
IdentificationBack Directory
[Name]

Triphosphopyridine nucleotide
[CAS]

53-59-8
[Synonyms]

TPN
TPNH
NADP
NADPH
Co II
NADP-ox
beta-tpn
BETA-NADP
cozymaseii
COENZYME II
nadphosphate
codehydraseii
NADP-oxidized
ATRAZINE NEAT
tpn(nucleotide)
nadide phosphate
CODEHYDROGENASE II
Triphosphopyridine n
Triphosphopyridinnucleotid
Triphosphopyridine nucleotid
TRIPHOSPHOPYRIDINE NUCLEOTIDE
CHLOROETHANE 200UG/ML IN METHANOL
BOTTLE 2,5L SMALL BROWN GLASS DIN45
nicotinamide adenine dinucleotide-P
NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE
BETA-NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE
B-NICOTINAMIDEADENINEDINUCLEOTIDEPHOSPHATE,HYDRATE
B-NICOTINAMIDE ADENINE DINUCLEOTIDE*PHOS PHATE FREE
β-Nicotinamide adenine dinucleotide phosphate (NADP)
β-nicotinamide adenine dinucleotide phosphate hydrate
BETA-NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHORIC ACID
BETA-NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE REDUCED
BETA-NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE (NADP+)
NADP(β-Nicotinamide adenine dinucleotide phosphate hydrate)
β-nicotinamide adenine dinucleotide phosphate(NADP+) free base
NADP (b-NicotinaMide adenine dinucleotide phosphate)trihydrate
Beta-nicotinamide adenine dinucleotide phosphate(NADP+) free base
β-NADP, Coenzyme II, NADP, TPN, Triphosphopyridine nucleotide
enosine2’-(dihydrogenphosphate)5’-(trihydrogenpyrophosphate),innersalt
2’-(dihydrogenphosphate),5’.fwdarw.’-adenosine5’-(trihydrogendiphosphate
5'-ester with3-(aminocarbonyl)-1-b-D-ribofuranosylpyridinium, inner salt
Adenosine5'-(trihydrogen diphosphate), 2'-(dihydrogen phosphate), P'®
β-Nicotinamide Adenine Dinucleotide Phosphate [for Biochemical Research]
pyridinium,3-carbamoyl-1-beta-d-ribofuranosyl-,hydroxide,5’,5’-esterwithad
esterwith3-(aminocarbonyl)-1-beta-d-ribofuranosylpyridiniumhydroxide,inner
beta-NicotinaMide Adenine Dinucleotide Phosphate [for BiocheMical Research]
β-Nicotinamide adenine dinucleotide phosphate hydrate,β-NADP, CoenzymeII, NADP, TPN, Triphosphopyridine nucleotide
[(2R,3R,4R,5R)-2-(6-aminopurin-9-yl)-5-[[[[(2R,3S,4R,5R)-5-(5-carbamoylpyridin-1-yl)-3,4-dihydroxy-oxolan-2-yl]methoxy-hydroxy-phosphoryl]oxy-hydroxy-phosphoryl]oxymethyl]-4-hydroxy-oxolan-3-yl]oxyphosphonic acid
[EINECS(EC#)]

200-178-1
[Molecular Formula]

C21H28N7O17P3
[MDL Number]

MFCD00067537
[MOL File]

53-59-8.mol
[Molecular Weight]

743.41
Chemical PropertiesBack Directory
[Definition]

The oxidized form of nicotinamide adenine dinucleotide phosphate (NADP) that receives electrons from photosystem I during photosynthesis. It exists as an anion under normal physiologic conditions.
[storage temp. ]

−20°C
[solubility ]

H2O: 50 mg/mL, clear, slightly yellow
[form ]

powder to crystal
[pka]

pKa1 3.9; pKa2 6.1(at 25℃)
[color ]

White to Orange to Green
[λmax]

260nm(lit.)
[Merck ]

14,6348
[InChIKey]

XJLXINKUBYWONI-WFYQBQJJNA-N
[EPA Substance Registry System]

Adenosine 5'-(trihydrogen diphosphate), 2'-(dihydrogen phosphate), P'.fwdarw.5'-ester with 3-(aminocarbonyl)-1-.beta.D-ribofuranosylpyridinium, inner salt(53-59-8)
Safety DataBack Directory
[Hazard Codes ]

Xi
[Risk Statements ]

36/37/38
[Safety Statements ]

26-36
[WGK Germany ]

3
[RTECS ]

UU3440000
[F ]

10-21
[HS Code ]

2934.99.9001
Raw materials And Preparation ProductsBack Directory
[Raw materials]

AMBERLITE(R) IRC-50-->Trichloroacetic acid-->[(2R,5R)-5-(6-aminopurin-9-yl)-3-hydroxy-4-phosphonooxy-oxolan-2-yl]me thoxyphosphonic acid
[Preparation Products]

11-BETA,17-ALPHA,21-TRIHYDROXY-5-BETA-PREGNANE-3,20-DIONE-->5-amino-2,5-dioxo-pentanoic acid-->NADPH
Hazard InformationBack Directory
[Description]

Triphosphopyridine nucleotide is a coenzyme composed of ribosylnicotinamide 5'-phosphate (NMN) coupled by pyrophosphate linkage to the 5'-phosphate adenosine 2',5'-bisphosphate. Triphosphopyridine nucleotide serves as an electron carrier in a number of reactions, being alternately oxidized (NADP+) and reduced (NADPH).
[Chemical Properties]

Triphosphopyridine nucleotide is white or off-white powder, it is easy to absorb moisture and deliquescence. pKa{1}=3.9; pKa{2}=6.1. It is soluble in water, methanol, insoluble in ethanol, insoluble in ether and ethyl acetate.
[Uses]

β-Nicotinamide adenine dinucleotide phosphate hydrate is suitable for use in:
the measurement of Glucose-6-phosphate dehydrogenase activity
the Cytochrome P450 3A4 assay as a part of NADPH-regenerating system
the Cytochrome P450 2D6 assay as a part of NADPH-regenerating system
the determination of Glucose-6-phosphate content
[Biological Functions]

Triphosphopyridine nucleotide (NADP) serves as an electron carrier in a number of reactions, being alternately oxidized (NADP+) and reduced (NADPH).
[Biochem/physiol Actions]

β-Nicotinamide adenine dinucleotide 2′-phosphate (NADP+) and β-Nicotinamide adenine dinucleotide 2′-phosphate, reduced (NADPH) comprise a coenzyme redox pair (NADP+:NADPH) involved in a wide range of enzyme catalyzed oxidation reduction reactions. The NADP+/NADPH redox pair facilitates electron transfer in anabolic reactions such as lipid and cholesterol biosynthesis and fatty acyl chain elongation. The NADP+/NADPH redox pair is used in a variety of antioxidation mechanism where it protects agains reactive oxidation species accumulation. NADPH is generated in vivio by the pentose phosphate pathway (PPP).
[Synthesis]

Triphosphopyridine nucleotide is prepared by the reaction of NADPH. It is synthesised mainly by the interaction of both NfrA1 enzyme and a Bacillus subtilis under the conditions of bacterial luciferase. Reaction conditions were as follows: with hydrogenchloride; NfrA1 enzyme; nitrofurazone; 2-amino-2-hydroxymethyl-1,3-propanediol In water at 23℃; pH=7.0; Enzyme kinetics; Further Variations; Reagents; Oxidation.
Triphosphopyridine nucleotide synthesis
[Purification Methods]

Purify NMN by passage through a column of Dowex-1 (Clform) and washing with H2O until no absorbance is observed at 260 nm. The tubes containing NMN are pooled, adjusted to pH 5.5-6 and evaporated in vacuo to a small volume. This is adjusted to pH 3 with dilute HNO3 in an ice-bath and treated with 20volumes of Me2CO at 0-5o. The heavy white precipitate is collected by centrifugation at 0o. It is best stored wet and frozen or it can be dried to give a gummy residue. It has max 266nm ( 4,600) and min 249nm ( 3600) at pH 7.0 (i.e. no absorption at 340nm). It can be estimated by reaction with CNor hydrosulfite which form the 4-adducts (equivalent to NADH) which have UV max 340nm ( 6,200). Thus after reaction, an OD340 of one is obtained from a 0.1612mM solution in a 1cm path cuvette. [Plaut & Plaut Biochemical Preparations 5 56 1957, Maplan & Stolzenbach Methods Enzymol 3 899 1957, Kaplan et al. J Am Chem Soc 77 815 1955, Beilstein 22/2 V 168.]
Spectrum DetailBack Directory
[Spectrum Detail]

Triphosphopyridine nucleotide(53-59-8)IR1
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