1184-16-3

Basic information

• Product Name: BETA-NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE SODIUM SALT
• Synonyms: CO II, NA;COENZYME II SODIUM SALT;BETA-NADP MONOSODIUM SALT;BETA-NADP-NA;BETA-NADP SODIUM SALT;BETA-NADP SODIUM SALT, HYDRATE;BETA-NICOTINAMIDE-ADENINE DINUCLEOTIDE PHOSPHATE, MONOSODIUM SALT;BETA-NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE SODIUM SALT
• CAS NO: 1184-16-3
• Molecular Formula: C₂₁H₂₇N₇O₁₇P₃*Na
• Molecular Weight: 765.39
• EINECS: 214-664-6
• Product Categories: nucleoside;Enzymes and Coenzymes in Nucleic Acids;Biochemistry;Nucleosides, Nucleotides & Related Reagents;Vitamin Related Compounds;Vitamins
• Mol File: 1184-16-3.mol
• Article Data: 1

Chemical Properties

• Melting Point: 175-178 °C (dec.)(lit.)
• Appearance: off-white to yellow/powder
• Storage Temp.: −20°C
• Solubility: H2O: 50 mg/mL
• Water Solubility: Soluble in water.
• Merck: 14,6344
• BRN: 4779954
• CAS DataBase Reference: BETA-NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE SODIUM SALT(CAS DataBase Reference)
• NIST Chemistry Reference: BETA-NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE SODIUM SALT(1184-16-3)
• EPA Substance Registry System: BETA-NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE SODIUM SALT(1184-16-3)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 36-36/37/38
• Safety Statements: 22-24/25-37/39-36-26
• WGK Germany: 3
• RTECS: UU3440000
• Hazardous Substances Data: 1184-16-3(Hazardous Substances Data)

Usage

Chemical Properties

White to slightly yellowish powder

Uses

Different sources of media describe the Uses of 1184-16-3 differently. You can refer to the following data:
1. 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. β-Nicotinamide Adenine Dinucleotide Phosphate Sodium Salt Hydrate is a substrate NADP which plays a role in a variety of metabolic processes.
2. β-Nicotinamide adenine dinucleotide phosphate monosodium salt acts as an electron acceptor used by cells. It is also useful in vitro to study NADP. Furthermore, it is used in a wide range of enzyme catalyzed oxidation reduction reactions. The combination of NADP+/NADPH is employed in a variety of antioxidation mechanisms, which protect against reactive oxidation species accumulation.

Biochem/physiol Actions

Electron acceptor

Synthetic route

sodium β-nicotinamide adenine dinucleotide phosphate → β-nicotinamide adenine dinucleotide phosphate sodium salt (1184-16-3)

Conditions	Yield
With metaphosphate In water at 37℃; for 2h; enzyme from Brevibacterium ammoniagenes, MgCl2, (Tris)-HCl buffer (pH 7.0);

β-nicotinamide adenine dinucleotide phosphate sodium salt (1184-16-3) → <4-2H1>NADP

Conditions	Yield
With cyanide(1-); deuterium	92%

5-(3-aminopropyl)nicotinic acid + β-nicotinamide adenine dinucleotide phosphate sodium salt (1184-16-3) → 1-[(2R,3R,4S,5R)-5-[[[[(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-3-hydroxy-4-phosphonooxyoxolan-2-yl]methoxyhydroxyphosphoryl]oxy-hydroxyphosphoryl]oxymethyl]-3,4-dihydroxyoxolan-2-yl]pyridin-1-ium-5-(3-aminopropyl)-3-carboxylic acid

Conditions	Yield
Stage #1: 5-(3-aminopropyl)nicotinic acid With sodium hydroxide In water at 37℃; for 1h; pH=4; Inert atmosphere; Stage #2: β-nicotinamide adenine dinucleotide phosphate sodium salt In water for 0.0833333h; pH=4; Inert atmosphere; Stage #3: With Aplysia californica ADP-ribosyl cyclase In water at 37℃; for 6h; pH=4; Inert atmosphere; Enzymatic reaction;	66%

5-hydroxynicotinic acid (27828-71-3) + β-nicotinamide adenine dinucleotide phosphate sodium salt (1184-16-3) → 1-[(2R,3R,4S,5R)-5-[[[[(2R,3R,4R5R)-5-(6-aminopurin-9-yl)-3-hydroxy-4-phosphonooxyoxolan-2-yl]methoxyhydroxyphosphoryl]oxyhydroxyphosphoryl]oxymethyl]-3,4-dihydroxyoxolan-2-yl]pyridin-1-ium-5-hydroxy-3-carboxylic acid

Conditions	Yield
Stage #1: 5-hydroxynicotinic acid With sodium hydroxide In water at 37℃; for 1h; pH=4; Inert atmosphere; Stage #2: β-nicotinamide adenine dinucleotide phosphate sodium salt In water for 0.0833333h; pH=4; Inert atmosphere; Stage #3: With Aplysia californica ADP-ribosyl cyclase In water at 37℃; for 2h; pH=4; Inert atmosphere; Enzymatic reaction;	63%

5-(3-hydroxypropyl)nicotinic acid + β-nicotinamide adenine dinucleotide phosphate sodium salt (1184-16-3) → 1-[(2R,3R,4S,5R)-5-[[[[(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-3-hydroxy-4-phosphonooxyoxolan-2-yl]methoxyhydroxyphosphoryl]oxyhydroxyphosphoryl]oxymethyl]-3,4-dihydroxyoxolan-2-yl]pyridin-1-ium-5-(3-hydroxypropyl)-3-carboxylic acid

Conditions	Yield
Stage #1: 5-(3-hydroxypropyl)nicotinic acid With sodium hydroxide In water at 37℃; for 1h; pH=4; Inert atmosphere; Stage #2: β-nicotinamide adenine dinucleotide phosphate sodium salt In water for 0.0833333h; pH=4; Inert atmosphere; Stage #3: With Aplysia californica ADP-ribosyl cyclase In water at 37℃; for 4h; pH=4; Inert atmosphere; Enzymatic reaction;	59%

5-(3-acetamidopropyl)nicotinic acid + β-nicotinamide adenine dinucleotide phosphate sodium salt (1184-16-3) → 1-[(2R,3R,4S,5R)-5-[[[[(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-3-hydroxy-4-phosphonooxyoxolan-2-yl]methoxyhydroxyphosphoryl]oxyhydroxyphosphoryl]oxymethyl]-3,4-dihydroxyoxolan-2-yl]pyridin-1-ium-5-(3-acetamidopropyl)-3-carboxylic acid

Conditions	Yield
Stage #1: 5-(3-acetamidopropyl)nicotinic acid With sodium hydroxide In water at 37℃; for 1h; pH=4; Inert atmosphere; Stage #2: β-nicotinamide adenine dinucleotide phosphate sodium salt In water for 0.0833333h; pH=4; Inert atmosphere; Stage #3: With Aplysia californica ADP-ribosyl cyclase In water at 37℃; for 5h; pH=4; Inert atmosphere; Enzymatic reaction;	58%

5-(3-azidopropyl)nicotinic acid + β-nicotinamide adenine dinucleotide phosphate sodium salt (1184-16-3) → 1-[(2R,3R,4S,5R)-5-[[[[(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-3-hydroxy-4-phosphonooxyoxolan-2-yl]methoxyhydroxyphosphoryl]oxyhydroxyphosphoryl]oxymethyl]-3,4-dihydroxyoxolan-2-yl]pyridin-1-ium-5-(3-azidopropyl)-3-carboxylic acid

Conditions	Yield
Stage #1: 5-(3-azidopropyl)nicotinic acid With sodium hydroxide In water at 37℃; for 1h; pH=4; Inert atmosphere; Stage #2: β-nicotinamide adenine dinucleotide phosphate sodium salt In water for 0.0833333h; pH=4; Inert atmosphere; Stage #3: With Aplysia californica ADP-ribosyl cyclase In water at 37℃; for 5h; pH=4; Inert atmosphere; Enzymatic reaction;	52%

5-thiomethyl nicotinic acid + β-nicotinamide adenine dinucleotide phosphate sodium salt (1184-16-3) → 1-[(2R,3R,4S,5R)-5-[[[[(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-3-hydroxy-4-phosphonooxyoxolan-2-yl]methoxyhydroxyphosphoryl]oxyhydroxyphosphoryl]oxymethyl]-3,4-dihydroxyoxolan-2-yl]pyridin-1-ium-5-thiomethyl-3-carboxylic acid

Conditions

Yield

Stage #1: 5-thiomethyl nicotinic acid With sodium hydroxide In water; dimethyl sulfoxide at 37℃; for 1h; pH=4; Inert atmosphere; Stage #2: β-nicotinamide adenine dinucleotide phosphate sodium salt In water; dimethyl sulfoxide for 0.0833333h; pH=4; Inert atmosphere; Stage #3: With Aplysia californica ADP-ribosyl cyclase In water; dimethyl sulfoxide at 37℃; for 2h; pH=4; Inert atmosphere; Enzymatic reaction;

51%

β-nicotinamide adenine dinucleotide phosphate sodium salt (1184-16-3) → C21H28BrN7O17P3(1+)

Conditions	Yield
With bromine; sodium acetate at 20℃; for 3h; pH=4.75; Inert atmosphere;	51%

β-nicotinamide adenine dinucleotide phosphate sodium salt (1184-16-3) + 3-carboxy-5-acetylaminopyridine (82817-65-0) → 1-[(2R,3R,4S,5R)-5-[[[[(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-3-hydroxy-4-phosphonooxyoxolan-2-yl]methoxyhydroxyphosphoryl]oxyhydroxyphosphoryl]oxymethyl]-3,4-dihydroxyoxolan-2-yl]pyridin-1-ium-5-acetamido-3-carboxylic acid

Conditions	Yield
Stage #1: 3-carboxy-5-acetylaminopyridine With sodium hydroxide In water at 37℃; for 1h; pH=4; Inert atmosphere; Stage #2: β-nicotinamide adenine dinucleotide phosphate sodium salt In water for 0.0833333h; pH=4; Inert atmosphere; Stage #3: With Aplysia californica ADP-ribosyl cyclase In water at 37℃; for 4h; pH=4; Inert atmosphere; Enzymatic reaction;	47%

5-(3-t-Boc-aminopropyl)nicotinic acid + β-nicotinamide adenine dinucleotide phosphate sodium salt (1184-16-3) → C29H43N7O20P3(1+)

Conditions

Yield

Stage #1: 5-(3-t-Boc-aminopropyl)nicotinic acid With sodium hydroxide In water; dimethyl sulfoxide at 37℃; for 1h; pH=4; Inert atmosphere; Stage #2: β-nicotinamide adenine dinucleotide phosphate sodium salt In water; dimethyl sulfoxide for 0.0833333h; pH=4; Inert atmosphere; Stage #3: With Aplysia californica ADP-ribosyl cyclase In water; dimethyl sulfoxide at 37℃; for 6h; pH=4; Inert atmosphere; Enzymatic reaction;

42%

β-nicotinamide adenine dinucleotide phosphate sodium salt (1184-16-3) → <4-2H2>NADPH (26852-07-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 92 percent / deuterium, cyanide ion 2: deuterium oxide, sodium dithionite View Scheme

nicotinic acid (59-67-6) + β-nicotinamide adenine dinucleotide phosphate sodium salt (1184-16-3) → 1-[(2R,3R,4S,5R)-5-[[[[(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-3-hydroxy-4-phosphonooxyoxolan-2-yl]methoxyhydroxyphosphoryl]oxyhydroxyphosphoryl]oxymethyl]-3,4-dihydroxyoxolan-2-yl]pyridin-1-ium-3-carboxylic acid

Conditions	Yield
Stage #1: nicotinic acid With sodium hydroxide In water at 37℃; for 1h; pH=4; Inert atmosphere; Stage #2: β-nicotinamide adenine dinucleotide phosphate sodium salt In water for 0.0833333h; pH=4; Inert atmosphere; Stage #3: With Aplysia californica ADP-ribosyl cyclase In water at 37℃; for 2h; pH=4; Inert atmosphere; Enzymatic reaction;

β-nicotinamide adenine dinucleotide phosphate sodium salt (1184-16-3) → C21H27BrN6O18P3(1+)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium acetate; bromine / 3 h / 20 °C / pH 4.75 / Inert atmosphere 2.1: sodium hydroxide / water; dimethyl sulfoxide / 1 h / 37 °C / pH 4 / Inert atmosphere 2.2: 0.08 h / pH 4 / Inert atmosphere 2.3: 2 h / 37 °C / pH 4 / Inert atmosphere; Enzymatic reaction View Scheme

β-nicotinamide adenine dinucleotide phosphate sodium salt (1184-16-3) → C21H26BrN9O18P3(1+)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium acetate; bromine / 3 h / 20 °C / pH 4.75 / Inert atmosphere 2.1: sodium hydroxide / water; dimethyl sulfoxide / 1 h / 37 °C / pH 4 / Inert atmosphere 2.2: 0.08 h / pH 4 / Inert atmosphere 2.3: 5 h / 37 °C / pH 4 / Inert atmosphere; Enzymatic reaction View Scheme

Relevant articles and documents

Metaphosphate: A New Phosphoryl Donor for NAD Phosphorylation

A new nicotinamid adenine dinucleotide (NAD) kinase which synthesizes nicotinamid adenine dinucleotide phosphate (NADP) from NAD and methaphosphate was found in some microorganisms.The activity of this enzyme, designated tentatively as methaphosphate-dependent NAD kinase, was detected in Acetobacter, Achromobacter, Brevibacterium, Corynebacterium and Micrococcus species, but was not detected in Escherichia, Proteus and Aerobacter species.The metaphosphate-dependent NAD kinase activity of Brevibacterium ammoniagenes IAM 1645 was not affected by culture conditions, though the adenosine-5'-triphosphate (ATP)-dependent NAD kinase activity was did.The metaphosphate-dependent NAD kinase activity from B. ammoniagenes also differed from the ATP-dependent NAD kinase activity in optimal pH of reaction and stability in heating and in freezing and thawing.Of phosphate polymers tested, the potent phosphoryl donor was metaphosphate alone, and other chain and ring phosphate polymers of different degrees of condensation were not utilized by this enzyme.