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NADP nicotinamide-adenine-dinucleotide phosphate

Catalog Number: BT-1197058

CAS Number: 108125-13-9

Molecular Formula: C21H29N7O17P3+

Molecular Weight: 744.4 g/mol

The product is for non-human research only. Not for therapeutic or veterinary use.

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Product Introduction

Description

Nicotinamide-adenine-dinucleotide phosphate (NADP) is a coenzyme that plays a crucial role in various biological processes, including energy metabolism, cellular signaling, and redox reactions. NADP is synthesized from nicotinamide-adenine-dinucleotide (NAD) by the addition of a phosphate group to the 2' position of the ribose ring. NADP exists in two forms, NADP+ and NADPH, which differ in their redox state. NADP+ is an oxidized form, while NADPH is a reduced form.

Properties

CAS Number

108125-13-9

Product Name

NADP nicotinamide-adenine-dinucleotide phosphate

IUPAC Name

[[(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-3-hydroxy-4-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2R,3S,4R,5R)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl hydrogen phosphate

Molecular Formula

C21H29N7O17P3+

Molecular Weight

744.4 g/mol

InChI

InChI=1S/C21H28N7O17P3/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/h1-4,7-8,10-11,13-16,20-21,29-31H,5-6H2,(H7-,22,23,24,25,32,33,34,35,36,37,38,39)/p+1/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1

InChI Key

XJLXINKUBYWONI-NNYOXOHSSA-O

SMILES

C1=CC(=C[N+](=C1)C2C(C(C(O2)COP(=O)(O)OP(=O)(O)OCC3C(C(C(O3)N4C=NC5=C(N=CN=C54)N)OP(=O)(O)O)O)O)O)C(=O)N

Synonyms

Coenzyme II
Dinucleotide Phosphate, Nicotinamide-Adenine
NADP
NADPH
Nicotinamide Adenine Dinucleotide Phosphate
Nicotinamide-Adenine Dinucleotide Phosphate
Nucleotide, Triphosphopyridine
Phosphate, Nicotinamide-Adenine Dinucleotide
Triphosphopyridine Nucleotide

Canonical SMILES

C1=CC(=C[N+](=C1)C2C(C(C(O2)COP(=O)(O)OP(=O)(O)OCC3C(C(C(O3)N4C=NC5=C(N=CN=C54)N)OP(=O)(O)O)O)O)O)C(=O)N

Isomeric SMILES

C1=CC(=C[N+](=C1)[C@H]2[C@@H]([C@@H]([C@H](O2)COP(=O)(O)OP(=O)(O)OC[C@@H]3[C@H]([C@H]([C@@H](O3)N4C=NC5=C(N=CN=C54)N)OP(=O)(O)O)O)O)O)C(=O)N

Method of Synthesis or Extraction

NADP nicotinamide-adenine-dinucleotide phosphate can be synthesized by various methods, including chemical synthesis, enzymatic synthesis, and microbial fermentation. Chemical synthesis involves the reaction of nicotinamide with adenosine triphosphate (ATP) in the presence of a strong acid catalyst. Enzymatic synthesis involves the use of enzymes, such as nicotinamide phosphoribosyltransferase (NAMPT) and nicotinamide mononucleotide adenylyltransferase (NMNAT), to catalyze the conversion of nicotinamide to NADP nicotinamide-adenine-dinucleotide phosphate. Microbial fermentation involves the use of microorganisms, such as Escherichia coli and Saccharomyces cerevisiae, to produce NADP nicotinamide-adenine-dinucleotide phosphate. The efficiency and yield of each method vary depending on the starting materials, reaction conditions, and purification methods. Chemical synthesis has a high yield but requires harsh reaction conditions and produces toxic byproducts. Enzymatic synthesis has a lower yield but is more environmentally friendly and produces fewer byproducts. Microbial fermentation has a moderate yield but requires a longer fermentation time and produces impurities that need to be removed. Safety considerations include the use of protective equipment, proper handling of chemicals, and disposal of waste.

Chemical Structure and Biological Activity

NADP nicotinamide-adenine-dinucleotide phosphate has a chemical structure consisting of a nicotinamide ring, an adenine ring, and a ribose phosphate backbone. The nicotinamide ring is responsible for the redox activity of NADP nicotinamide-adenine-dinucleotide phosphate, while the adenine ring is involved in the binding of NADP nicotinamide-adenine-dinucleotide phosphate to enzymes and other proteins. NADP nicotinamide-adenine-dinucleotide phosphate acts as a cofactor for various enzymes, including dehydrogenases, reductases, and transferases, which catalyze redox reactions in the cell. NADP nicotinamide-adenine-dinucleotide phosphate is also involved in the biosynthesis of nucleotides, fatty acids, and cholesterol. NADP nicotinamide-adenine-dinucleotide phosphateH is a reducing agent that is required for the biosynthesis of macromolecules, such as DNA and proteins, and for the detoxification of reactive oxygen species (ROS). NADP nicotinamide-adenine-dinucleotide phosphateH is also involved in the regeneration of glutathione, a major antioxidant in the cell.

Biological Effects

NADP nicotinamide-adenine-dinucleotide phosphate has various biological effects on cell function and signal transduction. NADP nicotinamide-adenine-dinucleotide phosphate is involved in the regulation of cellular metabolism, gene expression, and cell growth. NADP nicotinamide-adenine-dinucleotide phosphate also plays a role in the immune response, inflammation, and apoptosis. NADP nicotinamide-adenine-dinucleotide phosphate has potential therapeutic and toxic effects, depending on the context and concentration. NADP nicotinamide-adenine-dinucleotide phosphate has been implicated in various diseases, including cancer, diabetes, and neurodegenerative disorders. NADP nicotinamide-adenine-dinucleotide phosphate has been studied as a target for drug development, and several NADP nicotinamide-adenine-dinucleotide phosphate-dependent enzymes have been identified as potential drug targets.

Applications

NADP nicotinamide-adenine-dinucleotide phosphate has various applications in medical research, environmental research, and industrial research. In medical research, NADP nicotinamide-adenine-dinucleotide phosphate has been studied for its role in drug development, clinical trials, and findings. NADP nicotinamide-adenine-dinucleotide phosphate has been shown to have potential benefits in the treatment of cancer, diabetes, and other diseases. NADP nicotinamide-adenine-dinucleotide phosphate has also been studied for its potential side effects, such as toxicity and drug interactions. In environmental research, NADP nicotinamide-adenine-dinucleotide phosphate has been studied for its effects on ecosystems, role in pollution management, and sustainability and environmental impact. NADP nicotinamide-adenine-dinucleotide phosphate has been used as a biomarker for air pollution and acid rain. In industrial research, NADP nicotinamide-adenine-dinucleotide phosphate has been used in manufacturing processes, improving product quality and efficiency, and health and safety considerations. NADP nicotinamide-adenine-dinucleotide phosphate has been used as a cofactor in the production of various chemicals, such as amino acids, vitamins, and antibiotics.

Future Perspectives and Challenges

NADP nicotinamide-adenine-dinucleotide phosphate has several limitations in its use and study, including its instability, low solubility, and difficulty in purification. Possible solutions and improvements include the development of more stable and soluble analogs of NADP nicotinamide-adenine-dinucleotide phosphate, the use of new purification methods, and the identification of new enzymes and pathways involved in NADP nicotinamide-adenine-dinucleotide phosphate metabolism. Future trends and prospects in the application of NADP nicotinamide-adenine-dinucleotide phosphate in scientific research include the development of new drugs targeting NADP nicotinamide-adenine-dinucleotide phosphate-dependent enzymes, the use of NADP nicotinamide-adenine-dinucleotide phosphate as a biomarker for disease diagnosis and prognosis, and the exploration of the role of NADP nicotinamide-adenine-dinucleotide phosphate in aging and longevity.
Conclusion:
In conclusion, NADP nicotinamide-adenine-dinucleotide phosphate is a coenzyme that plays a crucial role in various biological processes. NADP nicotinamide-adenine-dinucleotide phosphate can be synthesized by various methods, including chemical synthesis, enzymatic synthesis, and microbial fermentation. NADP nicotinamide-adenine-dinucleotide phosphate has a chemical structure consisting of a nicotinamide ring, an adenine ring, and a ribose phosphate backbone. NADP nicotinamide-adenine-dinucleotide phosphate has various biological effects on cell function and signal transduction. NADP nicotinamide-adenine-dinucleotide phosphate has applications in medical research, environmental research, and industrial research. NADP nicotinamide-adenine-dinucleotide phosphate has several limitations in its use and study, and possible solutions and improvements are being explored. NADP nicotinamide-adenine-dinucleotide phosphate has future trends and prospects in the application of scientific research.

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