Adenosine 5'-(trihydrogen diphosphate), P'.fwdarw.5'-ester with 3-(aminocarbonyl)-1-beta-D-ribofuranosylpyridinium, inner salt

Base Information

• Chemical Name: Adenosine 5'-(trihydrogen diphosphate), P'.fwdarw.5'-ester with 3-(aminocarbonyl)-1-beta-D-ribofuranosylpyridinium, inner salt
• CAS No.: 53-84-9
• Molecular Formula: C21H27N7O14P2
• Molecular Weight: 663.431
• Hs Code.: 29349990
• Mol file: 53-84-9.mol

Synonyms:Adenosine 5'-(trihydrogen diphosphate), P'.fwdarw.5'-ester with 3-(aminocarbonyl)-1-.beta.-D-ribofuranosylpyridinium, inner salt

Chemical Property of Adenosine 5'-(trihydrogen diphosphate), P'.fwdarw.5'-ester with 3-(aminocarbonyl)-1-beta-D-ribofuranosylpyridinium, inner salt

Chemical Property:

• Appearance/Colour: White powder
• Melting Point: 140 - 142oC
• PSA: 340.71000
• LogP: -1.29620
• Storage Temp.: 2-8°C
• Solubility.: H2O: 50 mg/mL
• Water Solubility.: Soluble in water at 50mg/ml
• XLogP3: -6
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 18
• Rotatable Bond Count: 11
• Exact Mass: 663.10912256
• Heavy Atom Count: 44
• Complexity: 1120

Purity/Quality:

99% ^*data from raw suppliers

NAD ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,F,Xi
• Hazard Codes: Xn,F,Xi
• Statements: 36-68/20/21/22-20/21/22-40-22
• Safety Statements: 36-26-36/37-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• 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)O)O)O)O)C(=O)N
• Description: β-Nicotinamide adenine dinucleotide (NAD+) plays a major role in metabolism as a cofactor and mobile electron acceptor. NAD+ is a required oxidizing cosubstrate for many enzymes. It is reduced to NADH (Cat# N-035) which carries electrons to the electron transport chain for subsequent oxidative phorphorylation and ATP production. NAD+ is capable of donating ADP-ribose moieties to a protein, producing nicotinamide in the process. Sirtuin enzymes use NAD+ as a substrate to deacetylate proteins and direct activity between the nucleus and mitochondria. NAD+ is regenerated by fermentation and by oxidative phosphorylation.
• Uses: β-Nicotinamide Adenine Dinucleotide is a coeznyme consisting of an adenine base and a nicotinamide base connected by a pair of bridging phosphate group. β-Nicotinamide Adenine Dinucleotide acts as a c oenzyme in redox reactions, as a donor of ADP-ribose moieties in ADP-ribosylation reactions and also as a precursor of the second messenger molecule cyclic ADP-ribose. β-Nicotinamide Adenine Dinucleot ide also acts as a substrate for bacterial DNA ligases and a group of enzymes called sirtuins that use NAD+ to remove acetyl groups from proteins.

Technology Process of Adenosine 5'-(trihydrogen diphosphate), P'.fwdarw.5'-ester with 3-(aminocarbonyl)-1-beta-D-ribofuranosylpyridinium, inner salt

There total 31 articles about Adenosine 5'-(trihydrogen diphosphate), P'.fwdarw.5'-ester with 3-(aminocarbonyl)-1-beta-D-ribofuranosylpyridinium, inner salt which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 58.0%

nicotinamide mononucleotide (1094-61-7) + N,N'-dicyclohexyl-4-morpholinecarboxamidinium salt of adenosine-5'-phosphoromorpholidate (24558-92-7) → NAD (53-84-9,66844-06-2)

Guidance literature:

With magnesium sulfate; manganese(ll) chloride; In formamide; for 16h; Ambient temperature;

DOI:10.1039/a809930h

Reference yield:

NADH (58-68-4,443892-10-2) → NAD (53-84-9,66844-06-2)

Guidance literature:

With oxygen; coenzyme PQQ; In water; at 30 ℃; Rate constant; pH 6.7; other catalysts, without and with diaphorase;

DOI:10.1246/cl.1990.1949

Reference yield:

N1-(2,3,5-Tri-O-benzoyl-β-D-ribofuranosyl)-3-aminocarbonylpyridinium bromide (18784-01-5) → NAD (53-84-9,66844-06-2)

Guidance literature:

Multi-step reaction with 3 steps

1: NH₃ / methanol

2: 80 percent / POCl₃, PO(OMe)3 / 7 h / -5 - 0 °C

3: 58 percent / MnCl₂, MgSO₄ / formamide / 16 h / Ambient temperature

With trimethyl phosphite; ammonia; magnesium sulfate; manganese(ll) chloride; trichlorophosphate; In methanol; formamide;

DOI:10.1039/a809930h

upstream raw materials:

7,10-dimethyl-10H-benzo[g]pteridine-2,4-dione

NADH

2-<(7α-O-10-methyl-7-isoalloxyazinyl)methyl>-β-cyclodextrin

2-<(7α-O-10-methyl-7-isoalloxyazinyl)methyl>-α-cyclodextrin

Downstream raw materials:

NADH

nicotinamide mononucleotide

ADP‐ribofuranose

nicotinamide

Refernces

• 1、 Bresnahan, William T.,Elving, Philip J.. "The Role of Adsorption in the Initial One-Electron Electrochemical Reduction of Nicotinamide Adenine Dinucleotide (NAD+)". . p. 2379 - 2386. Retrieved 1981.
• 2、 Walt, David R.,Rios-Mercadillo, Victor M.,Auge, Jacques,Whitesides, George M.. "Synthesis of Nicotinamide Adenine Dinucleotide (NAD) from Adenosine Monophosphate (AMP)". . p. 7805 - 7806. Retrieved 1980.
• 3、 Keita, Bineta,Essaadi, Khalid,Nadjo, Louis,Desmadril, Michel. "Rate-limiting one-electron transfer in the oxidation of NADH by polyoxometalates". . p. 411 - 418. Retrieved 1995.
• 4、 Tezuka, Takafumi,Murayama, Yuko. "Formation of pyridine nucleotides under symbiotic and non-symbiotic conditions between soybean nodules and free-living rhizobia". . p. 637 - 644. Retrieved 2002.
• 5、 Bartlett, Philip N.,Simon, Evelyne. "Poly(aniline)-poly(acrylate) composite films as modified electrodes for the oxidation of NADH". . p. 2599 - 2606. Retrieved 2000.
• 6、 Mengele, Alexander K.,Weixler, Dominik,Chettri, Avinash,Maurer, Maite,Huber, Fabian Lukas,Seibold, Gerd M.,Dietzek, Benjamin,Eikmanns, Bernhard J.,Rau, Sven. "Switching the Mechanism of NADH Photooxidation by Supramolecular Interactions". supporting information. p. 16840 - 16845. Retrieved 2021/10/25.
• 7、 Li, JuanJuan,Tian, Zhenzhen,Zhang, Shumiao,Xu, Zhishan,Mao, Xudong,Zhou, Yumin,Liu, Zhe. "Organometallic ruthenium and iridium phosphorus complexes: Synthesis, cellular imaging, organelle targeting and anticancer applications". . . Retrieved 2019/02/20.