- Syntheses of nicotinamide riboside and derivatives: Effective agents for increasing nicotinamide adenine dinucleotide concentrations in mammalian cells
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A new two-step methodology achieves stereoselective synthesis of β-nicotinamide riboside and a series of related amide, ester, and acid nucleosides. Compounds were prepared through a triacetylatednicotinate ester nucleoside, via coupling of either ethylnicotinate or phenylnicotinate with 1,2,3,5-tetra-O-acetyl-β-D-ribofuranose. Nicotinamide riboside, nicotinic acid riboside, O-ethylnicotinate riboside, O-methylnicotinate riboside, and several N-alkyl derivatives increased NAD+ concentrations from 1.2-2.7-fold in several mammalian cell lines. These findings establish bioavailability and potent effects of these nucleosides in stimulating the increase of NAD+ concentrations in mammalian cells.
- Yang, Tianle,Chan, Noel Yan-Ki,Sauve, Anthony A.
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- The high-resolution crystal structure of periplasmic Haemophilus influenzae NAD nucleotidase reveals a novel enzymatic function of human CD73 related to NAD metabolism
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Haemophilus influenzae is a major pathogen of the respiratory tract in humans that has developed the capability to exploit host NAD(P) for its nicotinamide dinucleotide requirement. This strategy is organized around a periplasmic enzyme termed NadN (NAD n
- Garavaglia, Silvia,Bruzzone, Santina,Cassani, Camilla,Canella, Laura,Allegrone, Gianna,Sturla, Laura,Mannino, Elena,Millo, Enrico,De Flora, Antonio,Rizzi, Menico
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- Chemical synthesis method of beta-nicotinamide mononucleotide
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The invention provides a chemical synthesis method of beta-nicotinamide mononucleotide. The method comprises the following steps: taking 1, 2, 3, 5-tetrabenzoyloxy-2-C-methyl-beta-D-ribofuranose and nicotinamide as initial raw materials, and sequentially carrying out condensation reaction, benzoyl protecting group removal and phosphorylation reaction, so as to prepare the beta-nicotinamide mononucleotide. The high-purity beta-nicotinamide mononucleotide can be obtained through three steps of reaction (each step of reaction does not need purification) and one step of desalination purification. The method has the advantages of easily available raw materials, short reaction route, simple post-treatment, environmental protection and high total reaction yield, and is suitable for industrial production.
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Paragraph 0040; 0044-0045
(2021/11/10)
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- NICOTINAMIDE MONONUCLEOTIDE AND NICOTINAMIDE RIBOSIDE DERIVATIVES AND USE THEREOF IN THE TREATMENT OF VIRAL INFECTIONS AND RESPIRATORY COMPLICATIONS, IN PARTICULAR CAUSED BY INFLUENZAVIRUS OR CORONAVIRUS
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The present invention relates to Nicotinamide mononucleotide derivatives of formula (I) or (Ia) for use in the treatment and/or prevention of viral infections, such as respiratory infections. The present invention further relates to pharmaceutical composi
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- Β - nicotinamide mononucleotide preparation method
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The invention discloses a preparation method of β - nicotinamide mononucleotide. The preparation method of β - nicotinamide mononucleotide comprises the following steps: S1: in the presence of first solvent and catalyst, nicotinate and tetraacetyl - D - ribose undergo condensation reaction in first microchannel reactor to obtain the material A. The temperature of the condensation reaction is 51 - 80 °C, and the residence time of the condensation reaction is 0.5 - 10 min. S2: Material A Removal first of the solvent gives material B. S3: In the presence of second solvent, the material B and the liquid ammonia are subjected to an ammonolysis reaction to obtain the material C. S4: The mixture of material C and third solvent removed second solvent and unreacted liquid ammonia to give material D. S5: The material D phosphorylates and reacts with the phosphorylation auxiliary to obtain. The β - nicotinamide mononucleotide preparation method can effectively shorten the reaction time, improve the production efficiency, lower the side reaction and improve the product yield.
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- Preparation method of nicotinamide ribose, reduction state and salt of nicotinamide ribose
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The invention belongs to the technical field of organic synthesis. The invention discloses a preparation method of nicotinamide ribose. The method comprises the following steps: reacting an intermediate A with nicotinamide in the presence of TMSOTf to obt
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- Process preparation method of beta-nicotinamide mononucleotide
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The invention provides a process preparation method of beta-nicotinamide mononucleotide. With tetraacetylribose and niacinamide or ethyl nicotinate as starting materials, through main process steps ofcondensation, ammonolysis, chemical resolution, phosphorylation and the like, and through optimization of the process method, the beta-nicotinamide mononucleotide is prepared; the method is based onthe purposes of quality control and safety of the beta-nicotinamide mononucleotide, industrial batch production feasibility of a preparation process and the like; the preparation method is improved onthe basis of an original process route, optimizes the selected materials and reagents, controls the material amount and the like, and has the advantages of simplicity in operation, easiness in process amplification, higher yield, controllable final product quality, controllable safety and the like compared with the original preparation process.
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- Nicotinamide riboside-amino acid conjugates that are stable to purine nucleoside phosphorylase
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The nutraceutical Nicotinamide Riboside (NR), an efficacious biosynthetic precursor to NAD, is readily metabolized by the purine nucleoside phosphorylase (PNP). Access to the PNP-stable versions of NR is difficult because the glycosidic bond of NR is easily cleaved. Unlike NR, NRH, the reduced form of NR, offers sufficient chemical stability to allow the successful functionalisation of the ribosyl-moiety. Here, we report on a series of NRH and NR derived amino acid conjugates, generated in good to excellent yields and show that O5′-esterification prevents the PNP-catalyzed phosphorolysis of these NR prodrugs.
- Hayat, Faisal,Migaud, Marie E.
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supporting information
p. 2877 - 2885
(2020/04/28)
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- Crystal form 1A and crystal form 1B of beta-nicotinamide ribose chloride and preparation method of crystal form 1A and crystal form 1B
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The invention discloses a crystal form 1A and a crystal form 1B of beta-nicotinamide ribose chloride and preparation methods of the crystal form 1A and the crystal form 1B. In an X-ray powder diffraction pattern, the crystal form 1A has diffraction peaks with 2 theta of 13.0+/-0.2 degrees, 14.0+/-0.2 degrees, 23.8+/-0.2 degrees, 24.5+/-0.2 degrees and 25.4+/-0.2 degrees. In an X-ray powder diffraction pattern, the crystal form 1B has diffraction peaks with 2 theta of 5.0+/-0.2 degrees, 15.6+/-0.2 degrees, 21.6+/-0.2 degrees and 26.4+/-0.2 degrees. These two crystal forms of nicotinamide ribosehave more advantageous properties including substance morphology, stability (e.g., low content of solvent residue, low hygroscopicity, storage stability, polymorph transformation stability), solubility, chemical purity, and the like. The change of the properties is more beneficial to industrial production of high-purity nicotinamide ribose, and a wide space is provided for development of dosage forms of nicotinamide ribose.
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Paragraph 0056-0060; 0074-0077
(2020/11/02)
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- Preparation method of nicotinamide ribose
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The invention relates to a preparation method of nicotinamide ribose. The method comprises the steps that nicotinamide and 1,2,3,5-tetraacethyl-beta-D-ribofuranose serve as a synthetic starting material, and a finished nicotinamide ribose product is obtai
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Paragraph 0024-0029
(2019/11/28)
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- Method for synthesizing nicotinamide ribose
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The invention discloses a method for synthesizing nicotinamide ribose. The method comprises the following steps of dissolving 1-acetoxyl-2,3,5-triphenylformyloxy-beta-D-ribofuranose in toluene to obtain a mixed solution; adding hydrobromic acid in acetic
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Paragraph 0040-0051
(2019/08/07)
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- Method for preparing beta-niacinamide single nucleotide or beta-niacinamide ribose
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The invention belongs to the field of chemical synthesis, and particularly relates to a method for preparing beta-niacinamide single nucleotide or beta-niacinamide ribose, which aims at solving the technical problem of providing a method for preparing beta-niacinamide single nucleotide or beta-niacinamide ribose. The method comprises the following steps of performing condensation, deacetylation, phosphorylation and ammonolysis on ethyl niacinate and tetraacetyl ribose, so as to obtain the beta-niacinamide single nucleotide; performing condensation, deacetylation, and ammonolysis on ethyl niacinate and tetraacetyl ribose, so as to obtain the beta-niacinamide ribose. Compared with the conventional methods, the method has the advantages that the operation is simple, the amplification is easy,the purification is easy, the yield rate is high, and the like.
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Paragraph 0105; 0110-0113; 0118-0120
(2019/01/14)
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- PROCESS FOR PREPARATION OF NICOTINAMIDE RIBOSIDE (NR) AND COSMETIC COMPOSITION COMPRISING (NR AND A PHOSPHATE-BINDING AGENT
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Disclosed herein is a process for preparing nicotinamide riboside (NR) from an NR precursor and a phosphate-binding agent in a solvent. The reaction-derived mixture comprising NR may be further used without further processing in a variety of products, particularly in a cosmetic product.
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Page/Page column 22
(2017/09/15)
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- Chemical synthesis of the second messenger nicotinic acid adenine dinucleotide phosphate by total synthesis of nicotinamide adenine dinucleotide phosphate
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Signaling dinucleotides: The first single-isomer synthesis of nicotinamide adenine dinucleotide phosphate (NADP) is reported. Installation and maintenance of sensitive phosphate and pyridinium functionalities were key to success. Significantly, conversion
- Dowden, James,Moreau, Christelle,Brown, Richard S.,Berridge, Georgina,Galione, Antony,Potter, Barry V. L.
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p. 4637 - 4640
(2007/10/03)
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