Nicotinamide riboside

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Nicotinamide riboside
Nicotinamide-beta-riboside.svg
Nicotinamideriboside.png
Names
Preferred IUPAC name
3-Carbamoyl-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyridin-1-ium
Other names
1-(β-D-Ribofuranosyl)nicotinamide; N-Ribosylnicotinamide
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
UNII
  • InChI=1S/C11H14N2O5/c12-10(17)6-2-1-3-13(4-6)11-9(16)8(15)7(5-14)18
  • c1cc(c[n+](c1)[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O)C(=O)N
Properties
C11H15N2O5+
Molar mass 255.25 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Nicotinamide riboside (NR, SR647) is a pyridine-nucleoside and a form of vitamin B3, functioning as a precursor to nicotinamide adenine dinucleotide or NAD+.[1]

Chemistry[edit]

While the molecular weight of nicotinamide riboside is 255.25 g/mol,[2] that of its chloride salt is 290.70 g/mol.[3][4] As such, 100 mg of nicotinamide riboside chloride provides 88 mg of nicotinamide riboside. Recently, the crystal structure of a new series of crystalline forms of other nicotinamide riboside salts has been discovered. These salts correspond to different enantiomers of hydrogen tartrate and hydrogen malate and have a molecular weight of 404.33 and 388.33 g/mol respectively.[5]

History[edit]

Nicotinamide riboside (NR) was first described in 1944 as a growth factor, termed Factor V, for Haemophilus influenza, a bacterium that lives in and depends on blood. Factor V, purified from blood, was shown to exist in three forms: NAD+, NMN and NR. NR was the compound that led to the most rapid growth of this bacterium.[6] H. influenza cannot grow on nicotinic acid, nicotinamide, tryptophan or aspartic acid, which were the previously known precursors of NAD+.[7]

In 2000, yeast Sir2 was shown to be an NAD+-dependent protein lysine deacetylase,[8] which led several research groups to probe yeast NAD+ metabolism for genes and enzymes that might regulate lifespan.[9]

Synthesis[edit]

Different biosynthetic pathways are responsible for converting the different B3 vitamins into NAD+. The enzyme nicotinamide phosphoribosyltransferase (Nampt) catalyzes the rate-limiting step of the two-step pathway converting nicotinamide to NAD+.[10] NR kinase enzymes can also function as a salvage pathway for NAD+, but this pathway is not essential.[10]

Commercialization[edit]

ChromaDex licensed patents in July 2012, and began to develop a process to bring NR to market as TruNiagen.[11] ChromaDex claims copyright, and since 2016 has been in a patent dispute with Elysium Health over the rights to nicotinamide riboside supplements.[12]

Biosynth Carbosynth licensed a patent to produce new NR salts WO 2021013795 . The new carboxylic acid salts in crystalline form can be used in nutritional supplements and pharmaceutical compositions.

See also[edit]

References[edit]

  1. ^ Bogan, K.L., Brenner, C. (2008). "Nicotinic acid, nicotinamide, and nicotinamide riboside: a molecular evaluation of NAD+ precursor vitamins in human nutrition". Annu. Rev. Nutr. 28: 115–130. doi:10.1146/annurev.nutr.28.061807.155443. PMID 18429699.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  2. ^ "Nicotinamide riboside". pubchem.ncbi.nlm.nih.gov.
  3. ^ "GRAS Notices, GRN No. 635". www.accessdata.fda.gov. Retrieved 18 February 2019.
  4. ^ "Spherix/ChromaDex GRAS submission" (PDF). FDA.gov. Retrieved 18 February 2019.
  5. ^ Günter, S; et al. (2021). "New Crystalline Salts of Nicotinamide Riboside as Food Additives". Molecules. MDPI. 26 (9): 2729. doi:10.3390/molecules26092729. PMC 8125264. PMID 34066468.
  6. ^ Gingrich, W; Schlenk, F (June 1944). "Codehydrogenase I and Other Pyridinium Compounds as V-Factor for Hemophilus influenzae and H. parainfluenzae". Journal of Bacteriology. 47 (6): 535–50. doi:10.1128/JB.47.6.535-550.1944. PMC 373952. PMID 16560803.
  7. ^ Belenky, P.; et al. (2007). "NAD+ Metabolism in Health and Disease". Trends in Biochemical Sciences. 32 (1): 12–19. doi:10.1016/j.tibs.2006.11.006. PMID 17161604.
  8. ^ Imai, S.; et al. (2000). "Transcriptional silencing and longevity protein Sir2 is an NAD-dependent histone deacetylase". Nature. 403 (6771): 795–800. Bibcode:2000Natur.403..795I. doi:10.1038/35001622. PMID 10693811. S2CID 2967911.
  9. ^ Anderson; et al. (2003). "Nicotinamide and PNC1 govern lifespan extension by calorie restriction in Saccharomyces cerevisiae". Nature. 423 (6936): 181–185. Bibcode:2003Natur.423..181A. doi:10.1038/nature01578. PMC 4802858. PMID 12736687.
  10. ^ a b Fletcher RS, Lavery GG (2018). "The emergence of the nicotinamide riboside kinases in the regulation of NAD+ metabolism". Journal of Molecular Endocrinology. 61 (1): R107–R121. doi:10.1530/JME-18-0085. PMC 6145238. PMID 30307159.
  11. ^ "ChromaDex Licenses Exclusive Patent Rights for Nicotinamide Riboside (NR) Vitamin Technologies". 2012-07-16. Retrieved 15 February 2019.
  12. ^ Melody M. Bomgardner (2018). "Firms feud over purported age-fighting molecule". Chemical & Engineering News. 96 (33).