Nicotinamide riboside (NR, SR647) is a
pyridine
Pyridine is a basic heterocyclic organic compound with the chemical formula . It is structurally related to benzene, with one methine group replaced by a nitrogen atom. It is a highly flammable, weakly alkaline, water-miscible liquid w ...
-
nucleoside
Nucleosides are glycosylamines that can be thought of as nucleotides without a phosphate group. A nucleoside consists simply of a nucleobase (also termed a nitrogenous base) and a five-carbon sugar (ribose or 2'-deoxyribose) whereas a nucleoti ...
and a form of
vitamin B3, functioning as a precursor to
nicotinamide adenine dinucleotide
Nicotinamide adenine dinucleotide (NAD) is a coenzyme central to metabolism. Found in all living cells, NAD is called a dinucleotide because it consists of two nucleotides joined through their phosphate groups. One nucleotide contains an ade ...
or
NAD+
Nicotinamide adenine dinucleotide (NAD) is a coenzyme central to metabolism. Found in all living cells, NAD is called a dinucleotide because it consists of two nucleotides joined through their phosphate groups. One nucleotide contains an ade ...
.
Chemistry
While the molecular weight of nicotinamide riboside is 255.25 g/mol,
that of its chloride salt is 290.70 g/mol.
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.
History
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.
''H. influenza'' cannot grow on
nicotinic acid
Niacin, also known as nicotinic acid, is an organic compound and a form of vitamin B3, an essential human nutrient. It can be manufactured by plants and animals from the amino acid tryptophan. Niacin is obtained in the diet from a varie ...
,
nicotinamide
Niacinamide or Nicotinamide (NAM) is a form of vitamin B3 found in food and used as a dietary supplement and medication. As a supplement, it is used by mouth to prevent and treat pellagra (niacin deficiency). While nicotinic acid (niacin) ma ...
,
tryptophan
Tryptophan (symbol Trp or W)
is an α-amino acid that is used in the biosynthesis of proteins. Tryptophan contains an α-amino group, an α-carboxylic acid group, and a side chain indole, making it a polar molecule with a non-polar aromatic ...
or
aspartic acid
Aspartic acid (symbol Asp or D; the ionic form is known as aspartate), is an α-amino acid that is used in the biosynthesis of proteins. Like all other amino acids, it contains an amino group and a carboxylic acid. Its α-amino group is in the pro ...
, which were the previously known precursors of NAD+.
In 2000, yeast
Sir2 was shown to be an NAD+-dependent protein lysine deacetylase,
which led several research groups to probe yeast NAD+ metabolism for genes and enzymes that might regulate lifespan.
Synthesis
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+.
NR
kinase
In biochemistry, a kinase () is an enzyme that catalyzes the transfer of phosphate groups from high-energy, phosphate-donating molecules to specific substrates. This process is known as phosphorylation, where the high-energy ATP molecule don ...
enzymes can also function as a salvage pathway for NAD+, but this pathway is not essential.
Commercialization
ChromaDex
ChromaDex is a dietary supplement and food ingredient company based in Los Angeles, California founded in 1999 that is publicly traded on the NASDAQ.
In 2011, ChromaDex licensed patents from Dartmouth College, Cornell University, and Washington Un ...
licensed patents in July 2012, and began to develop a process to bring NR to market as TruNiagen.
ChromaDex claims copyright, and since 2016 has been in a patent dispute with
Elysium Health over the rights to nicotinamide riboside supplements.
Biosynth Carbosynth licensed a patent to produce new NR salts . The new carboxylic acid salts in crystalline form can be used in nutritional supplements and pharmaceutical compositions.
See also
*
Nicotinamide mononucleotide
*
Niacin
Niacin, also known as nicotinic acid, is an organic compound and a form of vitamin B3, an essential human nutrient. It can be manufactured by plants and animals from the amino acid tryptophan. Niacin is obtained in the diet from a variet ...
*
Nicotinamide
Niacinamide or Nicotinamide (NAM) is a form of vitamin B3 found in food and used as a dietary supplement and medication. As a supplement, it is used by mouth to prevent and treat pellagra (niacin deficiency). While nicotinic acid (niacin) ma ...
*
Vitamin B3
Vitamin B3, colloquially referred to as niacin, is a vitamin family that includes three forms or vitamers: niacin (nicotinic acid), nicotinamide (niacinamide), and nicotinamide riboside. All three forms of vitamin B3 are converted within the b ...
*
Nicotinamide adenine dinucleotide
Nicotinamide adenine dinucleotide (NAD) is a coenzyme central to metabolism. Found in all living cells, NAD is called a dinucleotide because it consists of two nucleotides joined through their phosphate groups. One nucleotide contains an ade ...
*
Sirtuin
Sirtuins are a family of signaling proteins involved in metabolic regulation. They are ancient in animal evolution and appear to possess a highly conserved structure throughout all kingdoms of life. Chemically, sirtuins are a class of proteins t ...
*
Poly (ADP-ribose) polymerase
References
{{Reflist
Ribosides
Nicotinamides