- An efficient chemical synthesis of nicotinamide riboside (NAR) and analogues
-
A simple and efficient synthesis of nicotinamide riboside (NAR) 1 and derivatives 4 and 5 via trimethylsilyl trifluoromethanesulfonate (TMSOTf)-mediated N-glycosilation followed by spontaneous deacetylation by treating with methanol is reported.
- Tanimori, Shinji,Ohta, Takeshi,Kirihata, Mitsunori
-
-
Read Online
- METHOD OF MAKING NICOTINAMIDE RIBOFURANOSIDE SALTS, NICOTINAMIDE RIBOFURANOSIDE SALTS AS SUCH, AND USES THEREOF
-
The present invention relates to a method of making nicotinamide ribofuranosie salts, in particular pharmaceutically acceptable nicotinamide ribofuranoside salts. The invention further relates to the nicotinamide ribofuranoside salts as such, in particular carboxylic acid salts in crystalline form, and their use in nutritional supplements and pharmaceutical compositions.
- -
-
Paragraph 00288-00290; 00292; 00296; 00299
(2021/01/29)
-
- New crystalline salts of nicotinamide riboside as food additives
-
NR+ is a highly effective vitamin B3 type supplement due to its unique ability to replenish NAD+ levels. While NR+ chloride is already on the market as a nutritional supplement, its synthesis is challenging, expensive, and low yielding, making it cumbersome for large-scale industrial production. Here we report the novel crystalline NR+ salts, D/L/DL-hydrogen tartrate and D/L/DL-hydrogen malate. Their high-yielding, one-pot manufacture does not require specific equipment and is suitable for multi-ton scale production. These new NR+ salts seem ideal for nutritional applications due to their bio-equivalence compared to the approved NR+ chloride. In addition, the crystal structures of all stereoisomers of NR+ hydrogen tartrate and NR+ hydrogen malate and a comparison to the known NR+ halogenides are presented.
- Haase, Robert,Hery-Barranco, Adrian,Pala, Laura,Parris, Jaclyn,Schabert, Günter,Spingler, Bernhard,Spitz, Urs
-
supporting information
(2021/05/26)
-
- NICOTINYL RIBOSIDE COMPOUNDS AND THEIR USES
-
The disclosure provides nicotinamide riboside (NR), the reduced form of NR (NRH), nicotinic acid riboside (NAR), the reduced form of NAR (NARH), derivatives thereof, compositions thereof and uses thereof. The NR and NAR derivatives have improved stability and bioavailability compared to NR and NAR. NR, NRH, NAR, NARH, and derivatives thereof can increase cellular NAD+ levels and enhance mitochondrial and cellular function and cell viability. Therefore, NR, NRH, NAR, NARH, and derivatives thereof, whether alone or in combination with one or more additional therapeutic agents (e.g., a mitochondrial uncoupler or/and a PARP inhibitor), are useful for treating mitochondrial diseases, mitochondria-related diseases and conditions, metabolic disorders, and other disorders and conditions.
- -
-
Paragraph 0711
(2021/01/22)
-
- NICOTINYL RIBOSIDE COMPOUNDS AND THEIR USES
-
The disclosure provides nicotinamide riboside (NR), the reduced form of NR (NRH), nicotinic acid riboside (NAR), the reduced form of NAR (NARH), derivatives thereof, compositions thereof and uses thereof. The NR and NAR derivatives have improved stability and bioavailability compared to NR and NAR. NR, NRH, NAR, NARH, and derivatives thereof can increase intracellular NAD+ levels, and can enhance mitochondrial and cellular function and cell viability. Therefore, NR, NRH, NAR, NARH, and derivatives thereof, whether alone or in combination with one or more additional therapeutic agents (e.g., a PARP inhibitor), are useful for treating mitochondrial diseases, mitochondria-related diseases and conditions, and other disorders and conditions.
- -
-
Page/Page column 4; 137-138
(2020/07/14)
-
- Scalable syntheses of traceable ribosylated NAD+ precursors
-
Nicotinamide adenine dinucleotide, NAD+, is an essential cofactor and substrate for many cellular enzymes. Its sustained intracellular levels have been linked to improved physiological end points in a range of metabolic diseases. Biosynthetic precursors to NAD+ include nicotinic acid, nicotinamide, the ribosylated parents and the phosphorylated form of the ribosylated parents. By combining solvent-assisted mechanochemistry and sealed reaction conditions, access to the ribosylated NAD+ precursors and to the isotopologues of NAD+ precursors was achieved in high yields and levels of purity. The latter is critical as it offers means to better trace biosynthetic pathways to NAD+, investigate the multifaceted roles of the intracellular NAD+ pools, and better exploit NAD+ biology.
- Makarov,Harris,Rodrigues,Migaud
-
supporting information
p. 8716 - 8720
(2019/10/16)
-
- Method for preparing niacinamide nucleoside salt
-
The invention relates to a method for preparing niacinamide nucleoside salt. The method comprises the following steps: replacing ions by niacinamide nucleoside trifluoromethane sulfonate prepared by deacetylation of triacetyl niacinamide nucleoside trifluoromethane in an organic solvent with acids, crystallizing to separate out a crude product, and pulping, thereby obtaining the corresponding niacinamide nucleoside salt. The ion replacement process in the invention overcomes the defects of chemical methods and extraction methods, and is suitable for industrial production.
- -
-
Paragraph 0025; 0027; 0029; 0031; 0033
(2018/12/02)
-
- NICOTINAMIDE RIBOSIDE DERIVATIVES AND THEIR USES
-
The disclosure provides derivatives of both the oxidized form and the reduced form of nicotinamide riboside (NR) and nicotinic acid riboside (NAR). The NR and NAR derivatives have improved stability and bioavailability compared to NR and NAR, and can increase cellular NAD+ levels and improve mitochondrial function. Therefore, the NR and NAR derivatives are useful for treating mitochondrial diseases, mitochondria-related diseases and conditions, and other disorders and conditions.
- -
-
Paragraph 0439; 0445; 0450
(2019/01/04)
-
- NICOTINAMIDE RIBOSIDE AND NICOTINAMIDE MONONUCLEOTIDE DERIVATIVES FOR USE IN THE TREATMENTS OF MITOCHONDRIAL-RELATED DISEASES
-
Provided herein are compounds of Formula (I): or a pharmaceutically acceptable salt thereof, and compositions comprising such compounds that are useful for increasing the amount of NAD+ in cells. Also disclosed are methods of using the disclosed compounds and compositions for treating mitochondrial-related diseases or disorders.
- -
-
Page/Page column 35; 36
(2017/06/20)
-
- PREPARATION AND USE OF CRYSTALLINE BETA-D-NICOTINAMIDE RIBOSIDE
-
Provided herein are crystalline beta-D-nicotinamide riboside chloride compositions and methods of preparation and use thereof. Also provided are related pharmaceutical compositions and methods of use thereof. The crystalline beta-D-nicotinamide riboside chloride compositions may be used to treat a disease or disorder that would benefit from increased NAD levels including a mitochondrial disease or disorder, insulin resistance, a metabolic syndrome, diabetes, obesity, or for increasing insulin sensitivity in a subject.
- -
-
-
- METHODS OF PREPARING NICOTINAMIDE RIBOSIDE AND DERIVATIVES THEREOF
-
The invention relates to methods of preparing nicotinamide riboside and derivatives thereof. In an aspect, the invention relates to a method of preparing a compound of formula (I), wherein n is 0 or 1; m is 0 or 1; Y is O or S; R1 is selected from H, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted primary or secondary amino, and substituted or unsubstituted azido; R2- R5, which may be the same or different, are each independently selected from H, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, and substituted or unsubstituted aryl; and X- is an anion, selected from an anion of a substituted or unsubstituted carboxylic acid, a halide, a substituted or unsubstituted sulfonate, a substituted or unsubstituted phosphate, a substituted or unsubstituted sulfate, a substituted or unsubstituted carbonate, and a substituted or unsubstituted carbamate.
- -
-
Page/Page column 21; 22
(2015/02/25)
-
- Synthesis of phosphodiester-type nicotinamide adenine dinucleotide analogs
-
Fourteen phosphodiester-type β-nicotinamide adenine dinucleotide (NAD+) analogs were prepared starting from nicotinamide. The phosphodiester linkage was effectively assembled in 69-93% yields via condensation reaction between 2′,3′-di-O-acetyl nicotinamide mononucleotide and alcohols in the presence of 2,4,6-triisopropylbenzenesulfonyl chloride. The analog β-nicotinamide ribose-5-(2-phenylethyl) phosphate showed beneficial effects on cell growth of model microorganisms.
- Liu, Wujun,Wu, Siguo,Hou, Shuhua,Zhao, Zongbao (Kent)
-
scheme or table
p. 8378 - 8383
(2009/12/28)
-
- Stereoselective synthesis of nicotinamide β-riboside and nucleoside analogs
-
A stereoselective synthesis of β-anomers of nicotinamide riboside (NAR), its deamidated analog (NaR), and of a nicotinamide C-methylated riboside derivative (NA3′-C-MeR) was developed. The β-anomers of N-ribofuranosylnicotine-3-carboxamide (β-NAR) and its nicotinic acid analog (β-NaR) were obtained by stereoselective synthesis via glycosylation of the presilylated bases under Vorbruggen's protocol. A NAR analog, methylated in position 3 of the ribosylic moiety, is also reported.
- Franchetti, Palmarisa,Pasqualini, Michela,Petrelli, Riccardo,Ricciutelli, Massimo,Vita, Patrizia,Cappellacci, Loredana
-
p. 4655 - 4658
(2007/10/03)
-