Uridine monophosphate
Encyclopedia
Uridine monophosphate, also known as 5'-uridylic acid and abbreviated UMP, is a nucleotide
that is used as a monomer
in RNA
. It is an ester
of phosphoric acid
with the nucleoside
uridine
. UMP consists of the phosphate
group
, the pentose
sugar
ribose
, and the nucleobase
uracil
; hence, it is a ribonucleoside monophosphate.
Another common shorthand for the molecule is uridylate - the deprotonated form of the molecule, which is predominant in aqueous solution. As a substituent
it takes the form of the prefix uridylyl-.
(orotidylic acid) in a decarboxylation reaction catalyzed by the enzyme
orotidylate decarboxylase. Uncatalyzed, the decarboxylation reaction is extremely slow (estimated to occur on average one time per 78 million years). Adequately catalyzed, the reaction takes place once per second, an increase of 1017-fold.
In humans, the orotidylate decarboxylase function is carried out by the protein UMP synthase. Defective UMP synthase can result in orotic aciduria
, a metabolic disorder.
(DHA) were found to have significantly improved performance in running mazes over those not fed the supplements, implying an increase in cognitive function.
. Uridine
is the active ingredient of the compound. A common misconception is that uridine and its compounds are not available in significant quantities from foods and must be obtained from expensive supplements or prescription drugs. This is not so. Uridine monophosphate is a major component of RNA
. Any food rich in RNA
, such as Brewer's yeast or some organ meats, will provide significant quantities of it. For more information, consult the article on uridine
.
Nucleotide
Nucleotides are molecules that, when joined together, make up the structural units of RNA and DNA. In addition, nucleotides participate in cellular signaling , and are incorporated into important cofactors of enzymatic reactions...
that is used as a monomer
Monomer
A monomer is an atom or a small molecule that may bind chemically to other monomers to form a polymer; the term "monomeric protein" may also be used to describe one of the proteins making up a multiprotein complex...
in RNA
RNA
Ribonucleic acid , or RNA, is one of the three major macromolecules that are essential for all known forms of life....
. It is an ester
Ester
Esters are chemical compounds derived by reacting an oxoacid with a hydroxyl compound such as an alcohol or phenol. Esters are usually derived from an inorganic acid or organic acid in which at least one -OH group is replaced by an -O-alkyl group, and most commonly from carboxylic acids and...
of phosphoric acid
Phosphoric acid
Phosphoric acid, also known as orthophosphoric acid or phosphoric acid, is a mineral acid having the chemical formula H3PO4. Orthophosphoric acid molecules can combine with themselves to form a variety of compounds which are also referred to as phosphoric acids, but in a more general way...
with the nucleoside
Nucleoside
Nucleosides are glycosylamines consisting of a nucleobase bound to a ribose or deoxyribose sugar via a beta-glycosidic linkage...
uridine
Uridine
Uridine is a molecule that is formed when uracil is attached to a ribose ring via a β-N1-glycosidic bond.If uracil is attached to a deoxyribose ring, it is known as a deoxyuridine....
. UMP consists of the phosphate
Phosphate
A phosphate, an inorganic chemical, is a salt of phosphoric acid. In organic chemistry, a phosphate, or organophosphate, is an ester of phosphoric acid. Organic phosphates are important in biochemistry and biogeochemistry or ecology. Inorganic phosphates are mined to obtain phosphorus for use in...
group
Functional group
In organic chemistry, functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. The same functional group will undergo the same or similar chemical reaction regardless of the size of the molecule it is a part of...
, the pentose
Pentose
A pentose is a monosaccharide with five carbon atoms. Pentoses are organized into two groups. Aldopentoses have an aldehyde functional group at position 1...
sugar
Sugar
Sugar is a class of edible crystalline carbohydrates, mainly sucrose, lactose, and fructose, characterized by a sweet flavor.Sucrose in its refined form primarily comes from sugar cane and sugar beet...
ribose
Ribose
Ribose is an organic compound with the formula C5H10O5; specifically, a monosaccharide with linear form H––4–H, which has all the hydroxyl groups on the same side in the Fischer projection....
, and the nucleobase
Nucleobase
Nucleobases are a group of nitrogen-based molecules that are required to form nucleotides, the basic building blocks of DNA and RNA. Nucleobases provide the molecular structure necessary for the hydrogen bonding of complementary DNA and RNA strands, and are key components in the formation of stable...
uracil
Uracil
Uracil is one of the four nucleobases in the nucleic acid of RNA that are represented by the letters A, G, C and U. The others are adenine, cytosine, and guanine. In RNA, uracil binds to adenine via two hydrogen bonds. In DNA, the uracil nucleobase is replaced by thymine.Uracil is a common and...
; hence, it is a ribonucleoside monophosphate.
Another common shorthand for the molecule is uridylate - the deprotonated form of the molecule, which is predominant in aqueous solution. As a substituent
Substituent
In organic chemistry and biochemistry, a substituent is an atom or group of atoms substituted in place of a hydrogen atom on the parent chain of a hydrocarbon...
it takes the form of the prefix uridylyl-.
Biosynthesis
Uridine monophosphate is formed from Orotidine 5'-monophosphateOrotidine 5'-monophosphate
Orotidine 5'-monophosphate , also known as orotidylic acid, is a pyrimidine nucleotide which is the last intermediate in the biosynthesis of uridine monophosphate. OMP is formed from orotate and phosphoribosyl pyrophosphate by the enzyme Orotate phosphoribosyltransferaseIn humans, the enzyme UMP...
(orotidylic acid) in a decarboxylation reaction catalyzed by the enzyme
Enzyme
Enzymes are proteins that catalyze chemical reactions. In enzymatic reactions, the molecules at the beginning of the process, called substrates, are converted into different molecules, called products. Almost all chemical reactions in a biological cell need enzymes in order to occur at rates...
orotidylate decarboxylase. Uncatalyzed, the decarboxylation reaction is extremely slow (estimated to occur on average one time per 78 million years). Adequately catalyzed, the reaction takes place once per second, an increase of 1017-fold.
In humans, the orotidylate decarboxylase function is carried out by the protein UMP synthase. Defective UMP synthase can result in orotic aciduria
Orotic aciduria
-Signs and symptoms:In addition to the characteristic excessive orotic acid in the urine, patients typically have megaloblastic anemia which cannot be cured by administration of vitamin B12 or folic acid....
, a metabolic disorder.
Effects on Animal Intelligence
In a recent study, gerbils fed supplements of uridine monophosphate, choline, and docosahexaenoic acidDocosahexaenoic acid
Docosahexaenoic acid is an omega-3 fatty acid that is a primary structural component of the human brain and retina. In chemical structure, DHA is a carboxylic acid with a 22-carbon chain and six cis double bonds; the first double bond is located at the third carbon from the omega end...
(DHA) were found to have significantly improved performance in running mazes over those not fed the supplements, implying an increase in cognitive function.
Uridine Monophosphate in Foods
In brain research studies such as those mentioned in this article, uridine monophosphate is used as a convenient delivery compound for uridineUridine
Uridine is a molecule that is formed when uracil is attached to a ribose ring via a β-N1-glycosidic bond.If uracil is attached to a deoxyribose ring, it is known as a deoxyuridine....
. Uridine
Uridine
Uridine is a molecule that is formed when uracil is attached to a ribose ring via a β-N1-glycosidic bond.If uracil is attached to a deoxyribose ring, it is known as a deoxyuridine....
is the active ingredient of the compound. A common misconception is that uridine and its compounds are not available in significant quantities from foods and must be obtained from expensive supplements or prescription drugs. This is not so. Uridine monophosphate is a major component of RNA
RNA
Ribonucleic acid , or RNA, is one of the three major macromolecules that are essential for all known forms of life....
. Any food rich in RNA
RNA
Ribonucleic acid , or RNA, is one of the three major macromolecules that are essential for all known forms of life....
, such as Brewer's yeast or some organ meats, will provide significant quantities of it. For more information, consult the article on uridine
Uridine
Uridine is a molecule that is formed when uracil is attached to a ribose ring via a β-N1-glycosidic bond.If uracil is attached to a deoxyribose ring, it is known as a deoxyuridine....
.
See also
- NucleosideNucleosideNucleosides are glycosylamines consisting of a nucleobase bound to a ribose or deoxyribose sugar via a beta-glycosidic linkage...
- NucleotideNucleotideNucleotides are molecules that, when joined together, make up the structural units of RNA and DNA. In addition, nucleotides participate in cellular signaling , and are incorporated into important cofactors of enzymatic reactions...
- DNADNADeoxyribonucleic acid is a nucleic acid that contains the genetic instructions used in the development and functioning of all known living organisms . The DNA segments that carry this genetic information are called genes, but other DNA sequences have structural purposes, or are involved in...
- RNARNARibonucleic acid , or RNA, is one of the three major macromolecules that are essential for all known forms of life....
- OligonucleotideOligonucleotideAn oligonucleotide is a short nucleic acid polymer, typically with fifty or fewer bases. Although they can be formed by bond cleavage of longer segments, they are now more commonly synthesized, in a sequence-specific manner, from individual nucleoside phosphoramidites...
- Pyrimidine biosynthesis
- Ribonucleoside monophosphate