Triphosphopyridine nucleotide
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Triphosphopyridine nucleotide
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CAS No:
53-59-8
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Formula:
C21H28N7O17P3
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Chemical Name:
Triphosphopyridine nucleotide
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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;TPNH;TRIPHOSPHOPYRIDINE NUCLEOTIDE;CODEHYDROGENASE II
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CAS No:
Description
NADP is nicotinamide adenine dinucleotide phosphate, acting as a key cofactor for electron transfer in the metabolism of all organisms, being alternately oxidized (NADP+) and reduced (NADPH).
Nicotinamide adenine dinucleotide phosphate. A coenzyme composed of ribosylnicotinamide 5'-phosphate (NMN) coupled by pyrophosphate linkage to the 5'-phosphate adenosine 2',5'-bisphosphate. It serves as an electron carrier in a number of reactions, being alternately oxidized (NADP+) and reduced (NADPH). (Dorland, 27th ed)
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.
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.
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.]
Triphosphopyridine nucleotide Basic Attributes
743.41
743.075453
200-178-1
TSCA listed
White to Orange to Green
2934.99.9001
Characteristics
260nm(lit.)
368
H2O: soluble 50mg/mL, clear, colorless to faintly yellow
−20°C
pKa1 3.9; pKa2 6.1(at 25℃)
Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
Triphosphopyridine nucleotide Use and Manufacturing
Fresh sheep liver is prepared by grinding and filtering, extracting with hot water at 80°C, treating with trichloroacetic acid, neutralizing to pH 5-6 with alkali, washing by centrifugal precipitation, purifying the crude product and replacing it with cation exchange resin, eluting with shaving, and refining and drying.
Biochemical research.
β-Nicotinamide adenine dinucleotide phosphate hydrate is suitable for use in:the measurement of Glucose-6-phosphate dehydrogenase activitythe Cytochrome P450 3A4 assay as a part of NADPH-regenerating systemthe Cytochrome P450 2D6 assay as a part of NADPH-regenerating systemthe determination of Glucose-6-phosphate content
Computed Properties
Molecular Weight:787.4
Hydrogen Bond Donor Count:6
Hydrogen Bond Acceptor Count:21
Rotatable Bond Count:12
Exact Mass:787.03934194
Monoisotopic Mass:787.03934194
Topological Polar Surface Area:373
Heavy Atom Count:50
Complexity:1280
Defined Atom Stereocenter Count:8
Covalently-Bonded Unit Count:3
Compound Is Canonicalized:Yes
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