Dictionary > Deoxyuridine monophosphate

Deoxyuridine monophosphate

Definition

noun
plural: uridine monophosphates
(biochemistry) A nucleotide composed of uracil, deoxyribose and a phosphate group, with a chemical formula: C9H13N2O8P

Details

Overview

A nucleotide is an organic compound made up of three subunits: a nucleobase, a five-carbon sugar, and a phosphate group. The sugar component may either be ribose or deoxyribose. The ribose is the sugar component of the nucleotides that make up RNA. The deoxyribose is the sugar component of DNA. Nucleotides are the monomeric units of nucleic acids. Each phosphate group connects the sugar rings of two adjacent nucleotide monomers. The phosphate groups and the sugar moieties form the backbone of a nucleic acid. The directionality of the chain runs from 5′-end to 3′-end. In DNA, the orientation of the two strands is in opposite directions. This is to allow complementary base pairing between nucleobase constituents. A nucleotide is, thus, a nucleoside with a phosphate group. Depending on the number of phosphate groups attached to the sugar moiety, it may be called nucleoside monophosphate (if with only one phosphate group), nucleoside diphosphate (with two phosphate groups), or nucleoside triphosphate (when with three phosphate groups). Depending on the pentose sugar component, a nucleoside may be a ribonucleoside or a deoxyribonucleoside. A ribonucleoside is a nucleoside with a ribose sugar component. (Depending on the nucleobase component, the ribonucleoside may be adenosine, guanosine, cytidine, uridine, or 5-methyluridine). A deoxyribonucleoside is a nucleoside with a deoxyribose sugar. Depending on the nucleobase component, a deoxyribonucleoside may be deoxyadenosine, deoxyguanosine, deoxycytidine, thymidine, or deoxyuridine. Also, depending on the nucleobase component, the nucleosides may be grouped into either the “double-ringed” purine or the “single-ringed” pyrimidine.
Deoxyuridine monophosphate (dUMP) is a pyrimidine nucleotide composed of uracil, deoxyribose and a phosphate group, with a chemical formula: C9H13N2O8P.

Characteristics

Deoxyuridine monophosphate (dUMP) is a nucleoside phosphate in being comprised of a deoxyribonucleoside and one phosphate group. This means that it has a deoxyribose as its sugar constituent with one phosphate group attached. Its nucleoside contains a pyrimidine base, i.e. uracil attached to the sugar. It has only one phosphate group attached to the nucleoside. Its conjugate base form is deoxyuridylate whereas its conjugate acid is deoxyuridylic acid.
Uridine monophosphate (UMP) is also a nucleoside but it differs from dUMP in having a ribose as its sugar component. Thus, its chemical formula is C9H13N2O9P.

Common biological reactions

Common biological reactions

Uracil, similar to other pyrimidines, is formed from a series of steps, beginning with the formation of carbamoyl phosphate. Carbamoyl phosphate forms from a reaction involving bicarbonate, glutamine, ATP, and water molecule. This process is catalyzed by the enzyme carbamoyl phosphate synthetase. The carbamoyl phosphate is then converted into carbamoyl aspartate through the catalytic activity of aspartate transcarbamylase. Carbamoyl aspartate is next converted into dihydroorotate, which is then oxidized to produce orotate. 5-phospho-α-D-ribosyl 1-pyrophosphate (PRPP), a ribose phosphate, reacts to orotate to form orotidine-5-monophosphate (OMP). OMP is decarboxylated by the enzyme OMP decarboxylase to yield uridine monophosphate (UMP). When the hydroxyl group at the 2’carbon of ribose of UMP with hydrogen, UMP becomes deoxygenated forming dUMP. dUMP may also be produced by the removal of phosphate groups from deoxyuridine diphosphate (dUDP) and from deoxyuridine triphosphate (dUTP). dUDP may be derived from uridine diphosphate through the converting action of the enzyme, ribonucleotide reductase. The addition of phosphate group in dUDP forms dUTP. UDP, in turn, are produced with the help of kinases that act on UMP and ATP. Phosphorylation of UDP produces UTP.

Biological functions

dUMP is an intermediate in deoxyribonucleotide metabolism. It may serve as a precursor to deoxythymidine monophosphate (dTMP). Uridine can be a source of thymidine (which is a nucleoside of thymine). In order to synthesize thymidine, uridine is reduced first to deoxyuridine (by the enzyme ribonucleotide reductase). After which, it is methylated by the enzyme thymidylate synthase to form thymidine.

Supplementary

Abbreviation(s)

  • dUMP
  • deoxy-UMP

Chemical formula

  • C9H13N2O8P
  • IUPAC name

    • {(2R,3S,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3-hydroxyoxolan-2-ylmethoxy}phosphonic acid

    Synonym

  • Deoxyuridine monophosphoric acid
  • Further reading

    See also


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