Triphosphopyridine nucleotide

Triphosphopyridine nucleotide Basic information
Product Name:Triphosphopyridine nucleotide
Synonyms:nadide phosphate;B-NICOTINAMIDE ADENINE DINUCLEOTIDE*PHOS PHATE FREE;β-nicotinamide adenine dinucleotide phosphate hydrate;B-NICOTINAMIDEADENINEDINUCLEOTIDEPHOSPHATE,HYDRATE;[(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;TPN;TPNH;TRIPHOSPHOPYRIDINE NUCLEOTIDE
CAS:53-59-8
MF:C21H28N7O17P3
MW:743.41
EINECS:200-178-1
Product Categories:53-59-8
Mol File:53-59-8.mol
Triphosphopyridine nucleotide Structure
Triphosphopyridine nucleotide Chemical Properties
storage temp. Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
solubility H2O: 50 mg/mL, clear, slightly yellow
pkapKa1 3.9; pKa2 6.1(at 25℃)
form powder to crystal
color White to Orange to Green
λmax260nm(lit.)
Merck 14,6348
InChIKeyXJLXINKUBYWONI-WFYQBQJJNA-N
EPA Substance Registry SystemAdenosine 5'-(trihydrogen diphosphate), 2'-(dihydrogen phosphate), P'.fwdarw.5'-ester with 3-(aminocarbonyl)-1-.beta.-D-ribofuranosylpyridinium, inner salt (53-59-8)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 26-36
WGK Germany 3
RTECS UU3440000
10-21
HS Code 2934.99.9001
MSDS Information
ProviderLanguage
SigmaAldrich English
Triphosphopyridine nucleotide Usage And Synthesis
DescriptionTriphosphopyridine 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 PropertiesTriphosphopyridine 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.
Usesβ-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
DefinitionThe 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.
Biological FunctionsTriphosphopyridine nucleotide (NADP) serves as an electron carrier in a number of reactions, being alternately oxidized (NADP+) and reduced (NADPH).
Biochem/physiol Actionsβ-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).
Purification MethodsPurify 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.]
β-Nicotinamide adenine dinucleotide NADPH, Tetrasodium Salt Ubidecarenone Adenine phosphate salt(1:1) Nicotinamide Adenine Tylosin phosphate AMPHISOL A Adenine phosphate(1:x) COENZYME Tributyl phosphate Trisodium phosphate Sodium Phosphate Monobasic Monohydrate Acetyl coenzyme A sodium salt 6-Thioguanine 2,3-Dimethoxy-5-methyl-p-benzoquinone phosphate Coenzyme A

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