Deoxycytidine monophosphate

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Deoxycytidine monophosphate
DCMP chemical structure.png
Deoxycytidine monophosphate anion 3D spacefill.png
Names
IUPAC name
2′-Deoxycytidylic acid
Systematic IUPAC name
[(2R,3S,5R)-5-(4-Amino-2-oxopyrimidin-1(2H)-yl)-3-hydroxyoxolan-2-yl]methyl dihydrogen phosphate
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.012.591 OOjs UI icon edit-ltr-progressive.svg
MeSH Deoxycytidine+monophosphate
PubChem CID
UNII
  • InChI=1S/C9H14N3O7P/c10-7-1-2-12(9(14)11-7)8-3-5(13)6(19-8)4-18-20(15,16)17/h1-2,5-6,8,13H,3-4H2,(H2,10,11,14)(H2,15,16,17)/t5-,6+,8+/m0/s1 Yes check.svgY
    Key: NCMVOABPESMRCP-SHYZEUOFSA-N Yes check.svgY
  • InChI=1/C9H14N3O7P/c10-7-1-2-12(9(14)11-7)8-3-5(13)6(19-8)4-18-20(15,16)17/h1-2,5-6,8,13H,3-4H2,(H2,10,11,14)(H2,15,16,17)/t5-,6+,8+/m0/s1
    Key: NCMVOABPESMRCP-SHYZEUOFBL
  • c1cn(c(=O)nc1N)[C@H]2C[C@@H]([C@H](O2)COP(=O)(O)O)O
Properties
C9H14N3O7P
Molar mass 307.199 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Deoxycytidine monophosphate (dCMP), also known as deoxycytidylic acid or deoxycytidylate in its conjugate acid and conjugate base forms, respectively, is a deoxynucleotide and one of the four monomers that make up DNA. In a DNA double helix, it will base pair with deoxyguanosine monophosphate. [1]

Contents

Medical use

Deoxycytidine monophosphate is a molecule of interest in treating genetic disorders such as thymidine kinase 2 (TK2) deficiency. In the case of TK2 deficiency, dCMP in conjunction with deoxythymidine monophosphate (dTMP) to bypass the deficiency in the TK2 enzyme. [2] Additionally dCMP is an indicator of several metabolite deficiency pathways such as UMP synthase deficiency or orotic aciduria. [3]

See also

Related Research Articles

<span class="mw-page-title-main">Deoxycytidine</span> Chemical compound

Deoxycytidine is a deoxyribonucleoside, a component of deoxyribonucleic acid. It is similar to the ribonucleoside cytidine, but with one hydroxyl group removed from the C2' position.

A salvage pathway is a pathway in which a biological product is produced from intermediates in the degradative pathway of its own or a similar substance. The term often refers to nucleotide salvage in particular, in which nucleotides are synthesized from intermediates in their degradative pathway.

<span class="mw-page-title-main">Thymidine kinase</span> Enzyme found in most living cells

Thymidine kinase is an enzyme, a phosphotransferase : 2'-deoxythymidine kinase, ATP-thymidine 5'-phosphotransferase, EC 2.7.1.21. It can be found in most living cells. It is present in two forms in mammalian cells, TK1 and TK2. Certain viruses also have genetic information for expression of viral thymidine kinases. Thymidine kinase catalyzes the reaction:

<span class="mw-page-title-main">Thymidine monophosphate</span> Chemical compound

Thymidine monophosphate (TMP), also known as thymidylic acid, deoxythymidine monophosphate (dTMP), or deoxythymidylic acid, is a nucleotide that is used as a monomer in DNA. It is an ester of phosphoric acid with the nucleoside thymidine. dTMP consists of a phosphate group, the pentose sugar deoxyribose, and the nucleobase thymine. Unlike the other deoxyribonucleotides, thymidine monophosphate often does not contain the "deoxy" prefix in its name; nevertheless, its symbol often includes a "d" ("dTMP"). Dorland’s Illustrated Medical Dictionary provides an explanation of the nomenclature variation at its entry for thymidine.

<span class="mw-page-title-main">Cytidine monophosphate</span> Chemical compound

Cytidine monophosphate, also known as 5'-cytidylic acid or simply cytidylate, and abbreviated CMP, is a nucleotide that is used as a monomer in RNA. It is an ester of phosphoric acid with the nucleoside cytidine. CMP consists of the phosphate group, the pentose sugar ribose, and the nucleobase cytosine; hence, a ribonucleoside monophosphate. As a substituent it takes the form of the prefix cytidylyl-.

<span class="mw-page-title-main">Purine nucleoside phosphorylase</span> Enzyme

Purine nucleoside phosphorylase, PNP, PNPase or inosine phosphorylase is an enzyme that in humans is encoded by the NP gene. It catalyzes the chemical reaction

<span class="mw-page-title-main">Foscarnet</span> Chemical compound

Foscarnet (phosphonomethanoic acid), known by its brand name Foscavir, is an antiviral medication which is primarily used to treat viral infections involving the Herpesviridae family. It is classified as a pyrophosphate analog DNA polymerase inhibitor. Foscarnet is the conjugate base of a chemical compound with the formula HO2CPO3H2 (Trisodium phosphonoformate).

<span class="mw-page-title-main">Nucleic acid metabolism</span> Process

Nucleic acid metabolism is a collective term that refers to the variety of chemical reactions by which nucleic acids are either synthesized or degraded. Nucleic acids are polymers made up of a variety of monomers called nucleotides. Nucleotide synthesis is an anabolic mechanism generally involving the chemical reaction of phosphate, pentose sugar, and a nitrogenous base. Degradation of nucleic acids is a catabolic reaction and the resulting parts of the nucleotides or nucleobases can be salvaged to recreate new nucleotides. Both synthesis and degradation reactions require multiple enzymes to facilitate the event. Defects or deficiencies in these enzymes can lead to a variety of diseases.

<span class="mw-page-title-main">Deoxycytidine kinase</span> Protein-coding gene in the species Homo sapiens

Deoxycytidine kinase (dCK) is an enzyme which is encoded by the DCK gene in humans. dCK predominantly phosphorylates deoxycytidine (dC) and converts dC into deoxycytidine monophosphate. dCK catalyzes one of the initial steps in the nucleoside salvage pathway and has the potential to phosphorylate other preformed nucleosides, specifically deoxyadenosine (dA) and deoxyguanosine (dG), and convert them into their monophosphate forms. There has been recent biomedical research interest in investigating dCK's potential as a therapeutic target for different types of cancer.

<span class="mw-page-title-main">Deoxyuridine monophosphate</span> Chemical compound

Deoxyuridine monophosphate (dUMP), also known as deoxyuridylic acid or deoxyuridylate in its conjugate acid and conjugate base forms, respectively, is a deoxynucleotide.

dCMP deaminase Protein-coding gene in the species Homo sapiens

dCMP deaminase is an enzyme which converts deoxycytidylic acid to deoxyuridylic acid.

In enzymology, a cytidylate kinase is an enzyme that catalyzes the chemical reaction

<span class="mw-page-title-main">UCK2</span> Protein-coding gene in the species Homo sapiens

Uridine-cytidine kinase 2 (UCK2) is an enzyme that in humans is encoded by the UCK2 gene.

<span class="mw-page-title-main">CMP kinase</span> Enzyme found in humans

UMP-CMP kinase is an enzyme that in humans is encoded by the CMPK1 gene.

<span class="mw-page-title-main">Thymidylate kinase</span>

Thymidylate kinase catalyzes the phosphorylation of thymidine 5'-monophosphate (dTMP) to form thymidine 5'-diphosphate (dTDP) in the presence of ATP and magnesium:

Discovery and development of nucleoside and nucleotide reverse-transcriptase inhibitors began in the 1980s when the AIDS epidemic hit Western societies. NRTIs inhibit the reverse transcriptase (RT), an enzyme that controls the replication of the genetic material of the human immunodeficiency virus (HIV). The first NRTI was zidovudine, approved by the U.S. Food and Drug Administration (FDA) in 1987, which was the first step towards treatment of HIV. Six NRTI agents and one NtRTI have followed. The NRTIs and the NtRTI are analogues of endogenous 2´-deoxy-nucleoside and nucleotide. Drug-resistant viruses are an inevitable consequence of prolonged exposure of HIV-1 to anti-HIV drugs.

(d)CMP kinase is an enzyme with systematic name ATP:(d)CMP phosphotransferase. This enzyme catalyses the following chemical reaction

<span class="mw-page-title-main">Mitochondrial DNA depletion syndrome</span> Medical condition

Mitochondrial DNA depletion syndrome, or Alper's disease, is any of a group of autosomal recessive disorders that cause a significant drop in mitochondrial DNA in affected tissues. Symptoms can be any combination of myopathic, hepatopathic, or encephalomyopathic. These syndromes affect tissue in the muscle, liver, or both the muscle and brain, respectively. The condition is typically fatal in infancy and early childhood, though some have survived to their teenage years with the myopathic variant and some have survived into adulthood with the SUCLA2 encephalomyopathic variant. There is currently no curative treatment for any form of MDDS, though some preliminary treatments have shown a reduction in symptoms.

Thymidine kinase is an enzyme, a phosphotransferase : 2'-deoxythymidine kinase, ATP-thymidine 5'-phosphotransferase, EC 2.7.1.21 that catalyzes the reaction:

<span class="mw-page-title-main">Thymidine kinase 2, mitochondrial</span> Protein-coding gene in the species Homo sapiens

Thymidine kinase 2, mitochondrial is a protein that in humans is encoded by the TK2 gene.

References

  1. "Human Metabolome Database: Showing metabocard for dCMP (HMDB0001202)". hmdb.ca. Retrieved 2024-12-10.
  2. Garone, Caterina; Garcia‐Diaz, Beatriz; Emmanuele, Valentina; Lopez, Luis C; Tadesse, Saba; Akman, Hasan O; Tanji, Kurenai; Quinzii, Catarina M; Hirano, Michio (August 2014). "Deoxypyrimidine monophosphate bypass therapy for thymidine kinase 2 deficiency". EMBO Molecular Medicine. 6 (8): 1016–1027. doi:10.15252/emmm.201404092. ISSN   1757-4676.
  3. PubChem. "Deoxycytidine 5'-monophosphate". pubchem.ncbi.nlm.nih.gov. Retrieved 2024-12-10.