3-(Aminocarbonyl)-1-(5-O-phosphonato-β-D-ribofuranosyl)pyridinium

BeschreibungNicotinamide mononucleotide (NMN), a product of the NAMPT reaction and a key NAD+ intermediate, ameliorates glucose intolerance by restoring NAD+ levels in HFD-induced T2D mice. NMN also enhances hepatic insulin sensitivity and restores gene expression related to oxidative stress, inflammatory response, and circadian rhythm, partly through SIRT1 activation. NMN is used for studying binding motifs within RNA aptamers and ribozyme activation processes involving β-nicotinamide mononucleotide (β-NMN)-activated RNA fragments.β-Nicotinamide mononucleotide (β-NMN) is an intermediate in the nicotinamide phosphoribosyltransferase (NAMPT)-catalyzed biosynthesis of nicotinamide adenine dinucleotide (NAD+). NAMPT mediates the condensation of nicotinamide with 5-phosphoribosyl-1-pyrophosphate to produce β-NMN. β-NMN adenyltransferase subsequently converts β-NMN to NAD+.

Verwendenβ-Nicotinamide mononucleotide (NMN) is used to study binding motifs within RNA aptamers and ribozyme activation processes involving β-nicotinamide mononucleotide (β-NMN)-activated RNA fragments. NMN is a nucleotide derived from ribose and nicotinamide. Niacinamide (nicotinamide,) is a derivative of vitamin B3, also known as niacin.) As a biochemical precursor of NAD+, it may be useful in the prevention of pellagra.β-Nicotinamide mononucleotide is an intermediate in the biosynthesis of nicotinamide adenine dinucleotide (NAD+). Nicotinamide phosphoribosyltransferase (Nampt) catalyzes the condensation of nicotinamide with 5-phosphoribosyl-1-pyrophosphate to generate β-NMN, which is subsequently converted to NAD+ by β-NMN adenyltransferase.At 50-100 μM, β-NMN has been used to enhance NAD biosynthesis and glucose-stimulated insulin secretion in a Nampt+/- mouse model of metabolic disease, demonstrating a role for Nampt in β cell function.Furthermore, at 500 mg/kg/day, it has been shown to ameliorate glucose intolerance in high-fat diet-induced type 2 diabetes mice by restoring NAD+ levels.

synthetischeβ-Nicotinamide mononucleotide is a NAD+intermediate. In recent years, the relation of NAD+metabolism and aging-associated disease is attracting attention from various research fields. Synthesis of β-nicotinamide mononucleotide (NMN) A solution of NAD (3.5 g, 5.28 mmol) and ZrCl4(6.15 g, 26.4 mmol) in 500 ml water was stirred at 50°C for 30 min. The hydrolysis was monitored by TLC (SiO2EtOH/ 1 M NH4Ac [7 : 3]). The reaction was quenched with 245mL of a 0.5 M solution of Na3PO4. After adjusting to pH 7 with a 2 M solution of HCl, a white precipitate was formed. The suspension was centrifuged 8 min,1,000rpm, the supernatant was collected and the pellet was washed two times with 200 mL water. The combined supernatants wereconcentrated to 1/3 of its volume on a rotary evaporator. The remaining solution was purified with a column filled with Dowex 50WX8 (100-200 mesh, H+-Form, column-material: 2.5 x 30 cm). The column was loaded with 1.5 L5 % HCl and equilibrated with1.5L millipore water until pH 5 was reached. 100 mL of the concentrated solution was loaded on the ion exchange column and eluted with Milliporewater. The first cleavage product eluted was NMN (615 mg, 1.84 mmol,yield:35 %) and yielded a colorless solid after evaporation of the solvent, followed by AMP. 1H NMR (500MHz, D2O)δ: 9.48 (s, 1 H), 9.31 (d,J= 6.2 Hz, 1 H), 9.00 (d,J= 8.2 Hz, 1 H), 8.32 (dd,J= 8.2, 6.2 Hz, 1 H), 6.24 (d,J=5.4 Hz, 1 H), 4.68-4.64 (m, 1 H), 4.58 (t, 1 H), 4.48-4.45 (m, 1 H), 4.36–4.14 (m,J= 12.0, 2 H). 13C NMR (75 MHz, d2o) δ: 165.50, 145.65, 142.15, 139.53, 133.62, 128.19, 99.65, 87.18, 87.06, 77.42, 70.71, 63.89, 63.82. 31P NMR (202 MHz, D2O)δ:-0.03

DefinitionChEBI: β-Nicotinamide Mononucleotide is a condensation product of nicotinamide and ribose 5-phosphate, in which the nitrogen of nicotinamide is linked to the (β) c-l of the ribose. NMN zwitterion is a nicotinamide mononucleotide. It has a role as an Escherichia coli metabolite and a mouse metabolite. It is a conjugate base of a NMN(+). It is a conjugate acid of a NMN(-).