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:

acetaldehyde

ADP‐ribofuranose

nicotinamide

α-1-O-methyl-ADP-ribose

Refernces

Biosynthesis of pipecolic acid by RapL, a lysine cyclodeaminase encoded in the rapamycin gene cluster

10.1021/ja0587603

The research presents an in-depth study on the biosynthesis of pipecolic acid by RapL, a lysine cyclodeaminase enzyme encoded in the rapamycin gene cluster. The main focus of the study is to validate RapL's ability to convert L-lysine to L-pipecolic acid through a cyclodeamination reaction involving redox catalysis. The researchers heterologously overexpressed and purified RapL, and conducted a series of experiments to confirm its enzymatic activity. They used L-lysine and L-[U-14C]ornithine as substrates, NAD+ as a cofactor, and analyzed the reactions using techniques such as cellulose thin layer chromatography (TLC), chiral radio-HPLC, and mass spectrometry. The study also investigated the enzyme's substrate specificity, cofactor requirements, and inhibitory properties. Additionally, the researchers used isotopically labeled substrates to dissect the mechanistic details of the cyclodeaminase reaction, confirming the loss of the R-amine and retention of the hydrogen atom at the R-carbon. The experiments provided the first in vitro characterization of a lysine cyclodeaminase and contributed to the understanding of the biosynthesis of medically important natural products like rapamycin, FK506, and FK520.

Nicotinamide-Containing Di- and Trinucleotides as Chemical Tools for Studies of NAD-Capped RNAs

10.1021/acs.orglett.8b03386

Agnieszka Mlynarska-Cieslak et al. discusses the chemical synthesis of nicotinamide adenine dinucleotide (NAD) cap analogues designed to be less susceptible to NAD-RNA degrading enzymes. The study aims to enhance the stability of NAD-capped RNAs for further biological studies. The authors synthesized a set of NAD analogues with modifications such as O-to-S substitutions at the pyrophosphate moiety and phosphorothioate/phosphorothiolate modifications. These analogues were incorporated into RNA transcripts using in vitro transcription with T7 polymerase. The modified RNAs were then tested for their susceptibility to deNADding enzymes like DXO, NudC, and Nudt12. The results identified several analogues that showed resistance to these enzymes, particularly compounds with combined modifications like a-PS and 2'-O-methylation.