carbanicotinamide adenine dinucleotide

Base Information

• Chemical Name: carbanicotinamide adenine dinucleotide
• CAS No.: 112345-60-5
• Molecular Formula: C22H29 N7 O13 P2
• Molecular Weight: 661.459
• Mol file: 112345-60-5.mol

Synonyms:Adenosine5'-(trihydrogen diphosphate),P'-[[4-[3-(aminocarbonyl)pyridinio]-2,3-dihydroxycyclopentyl]methyl] ester,inner salt, [1R-(1a,2b,3b,4a)]-

Chemical Property of carbanicotinamide adenine dinucleotide

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 331.48000
• Density: g/cm³
• LogP: -0.63260

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Use Description: Carbanicotinamide adenine dinucleotide (Carb-NAD+) is a chemical compound with potential applications in various fields, although it may not be as widely recognized as its counterpart NAD+. In the realm of biochemical research, it can serve as a valuable analog of NAD+ in studies related to enzyme kinetics, metabolic pathways, and redox reactions. Its role is fundamental in elucidating the mechanisms of NAD+-dependent enzymes and cellular processes. Additionally, in the pharmaceutical and biotechnology industries, Carb-NAD+ may find use as a tool in drug discovery and enzyme engineering, where its altered chemical structure can be exploited to design specific inhibitors or modulators of NAD+-dependent enzymes. While its significance varies within these fields, Carb-NAD+ consistently plays a crucial role in advancing our understanding of biochemical processes and may have potential applications in drug development and biotechnology.

Technology Process of carbanicotinamide adenine dinucleotide

There total 8 articles about carbanicotinamide adenine dinucleotide 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%

((1R,2R,3S,4R)-4-(3-carbamoylpyridin-1-ium-1-yl)-2,3-dihydroxycyclopentyl)methyl hydrogen phosphate (132486-54-5) + N,N'-dicyclohexyl-4-morpholinecarboxamidinium salt of adenosine-5'-phosphoromorpholidate (24558-92-7) → 1-((1R,2S,3R,4R)-4-((((((((2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)hydroxyphosphoryl)oxy)oxidophosphoryl)oxy)methyl)-2,3-dihydroxycyclopentyl)-3-carbamoylpyridin-1-ium (112345-60-5)

Guidance literature:

With pyridine; toluene-4-sulfonic acid; formamide; manganese(ll) chloride; at 25 ℃; for 20h; Inert atmosphere;

DOI:10.1021/jo301067e

Reference yield:

ATP disodium salt + chlorure de (-)-aminocarbonyl-3-(hydroxymethyl-cis-4-dihydroxy-trans-2,3-cyclopentyl) 1-pyridinium (102099-16-1,112344-69-1) → 1-((1R,2S,3R,4R)-4-((((((((2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)hydroxyphosphoryl)oxy)oxidophosphoryl)oxy)methyl)-2,3-dihydroxycyclopentyl)-3-carbamoylpyridin-1-ium (112345-60-5)

Guidance literature:

With magnesium(II) chloride hexahydrate; Phosphocreatine; creatinkinase; nicotine amide mononucleotide adenosyl transferase; ribosylkinase; In water; at 35 - 90 ℃; Enzymatic reaction;

Reference yield:

(-)-2-azabicyclo[2.2.1]hept-5-en-3-one (79200-56-9) → 1-((1R,2S,3R,4R)-4-((((((((2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)hydroxyphosphoryl)oxy)oxidophosphoryl)oxy)methyl)-2,3-dihydroxycyclopentyl)-3-carbamoylpyridin-1-ium (112345-60-5)

Guidance literature:

Multi-step reaction with 6 steps

1.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / i-Amyl alcohol; water; tert-butyl alcohol / 70 °C / Sealed tube

2.1: hydrogenchloride / 18 h / 25 °C

3.1: lithium triethylborohydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

3.2: 0.17 h / 0 °C

3.3: 25 °C

4.1: sodium acetate / methanol / 2 h / 25 °C

5.1: trimethyl phosphite; trichlorophosphate / methanol / 0 °C

6.1: toluene-4-sulfonic acid; pyridine; formamide; manganese(ll) chloride / 20 h / 25 °C / Inert atmosphere

With pyridine; trimethyl phosphite; hydrogenchloride; osmium(VIII) oxide; sodium acetate; lithium triethylborohydride; toluene-4-sulfonic acid; formamide; 4-methylmorpholine N-oxide; manganese(ll) chloride; trichlorophosphate; In tetrahydrofuran; methanol; i-Amyl alcohol; water; tert-butyl alcohol;

DOI:10.1021/jo301067e

upstream raw materials:

chlorure de (-)-aminocarbonyl-3-(hydroxymethyl-cis-4-dihydroxy-trans-2,3-cyclopentyl) 1-pyridinium

(-)-2-azabicyclo[2.2.1]hept-5-en-3-one

((1R,2R,3S,4R)-4-(3-carbamoylpyridin-1-ium-1-yl)-2,3-dihydroxycyclopentyl)methyl hydrogen phosphate

N,N'-dicyclohexyl-4-morpholinecarboxamidinium salt of adenosine-5'-phosphoromorpholidate

Refernces

• 1、 -. "METHOD AND SUBSTANCES FOR PREPARATION OF N-SUBSTITUTED PYRIDINIUM COMPOUNDS". Page/Page column 24-25. . Retrieved 2011/02/24.