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Uridine triphosphate

From Wikipedia, the free encyclopedia
Uridine triphosphate
Skeletal formula of UTP
Ball-and-stick model of the UTP molecule as an anion
Names
IUPAC name
Uridine 5′-(tetrahydrogen triphosphate)
Systematic IUPAC name
O1-{[(2R,3S,4R,5R)-5-(2,4-Dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-dihydroxyoxolan-2-yl]methyl} tetrahydrogen triphosphate
Identifiers
3D model (JSmol)
71520
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard100.000.508Edit this at Wikidata
EC Number
  • 200-558-7
307896
MeSHUridine+triphosphate
UNII
  • InChI=1S/C9H15N2O15P3/c12-5-1-2-11(9(15)10-5)8-7(14)6(13)4(24-8)3-23-28(19,20)26-29(21,22)25-27(16,17)18/h1-2,4,6-8,13-14H,3H2,(H,19,20)(H,21,22)(H,10,12,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1
    Key: PGAVKCOVUIYSFO-XVFCMESISA-N
  • O[C@@H]1[C@@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)O[C@H]([C@@H]1O)n1ccc(=O)[nH]c1=O
Properties
C9H15N2O15P3
Molar mass484.139 g·mol−1
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
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Chemical compound

Uridine-5′-triphosphate (UTP) is apyrimidinenucleoside triphosphate, consisting of theorganic baseuracil linked to the 1′ carbon of theribose sugar, and esterified with tri-phosphoric acid at the 5′ position. Its main role is as substrate for the synthesis ofRNA duringtranscription. UTP is the precursor for the production ofCTP viaCTP synthetase.[1] UTP can be biosynthesized fromUDP bynucleoside-diphosphate kinase after using thephosphate group fromATP.[2][3] UDP + ATP ⇌ UTP + ADP;[4] both UTP and ATP are energetically equal.[4]

The homologue in DNA isthymidine triphosphate (TTP or dTTP). UTP also has adeoxyribose form (dUTP).

Role in metabolism

[edit]

UTP also has the role of a source of energy or an activator of substrates in metabolic reactions, like that ofATP, but more specific. When UTP activates a substrate (such as glucose-1-phosphate), UDP-glucose is formed and inorganic phosphate is released.[5]UDP-glucose enters the synthesis ofglycogen. UTP is used in the metabolism ofgalactose, where the activated formUDP-galactose is converted to UDP-glucose.UDP-glucuronate is used to conjugatebilirubin to a more water-solublebilirubin diglucuronide. UTP is also used to activate amino sugars like glucosamine-1-phosphate to UDP-glucosamine, andN-acetyl-glucosamine-1-phosphate to UDP-N-acetylglucosamine.[6]

Role in receptor mediation

[edit]

UTP also has roles in mediating responses by extracellular binding to theP2Y receptors of cells. UTP and its derivatives are still being investigated for their applications in human medicine. However, there is evidence from various model systems to suggest it has applications in pathogen defense and injury repair. In mice UTP has been found to interact withP2Y4 receptors to mediate an enhancement inantibody production.[7] Inschwannoma cells, UTP binds to the P2YP receptors in the event of damage.  This leads to the downstream signal cascade that leads to the eventual injury repair.[8]

See also

[edit]

References

[edit]
  1. ^Meisenberg, Gerhard Meisenberg (2017).Principles of Medical Biochemistry. Philadelphia, PA, USA: Elsevier. p. 505.ISBN 978-0-323-29616-8.
  2. ^Victor, Rodwell (2015).Haper's illustrated Biochemistry. USA: McGraw-Hill. p. 118.ISBN 978-0-07-182537-5.
  3. ^Meisenberg, Gerhard Meisenberg (2017).Principles of MEDICAL BIOCHEMISTRY, 4th edition. Philadelphia, PA, USA: Elsevier. p. 59.ISBN 978-0-323-29616-8.
  4. ^abVoet, Donald (2011).Biochemistry, 4th edition. USA: JOHN WILEY & SONS, INC. p. 645.ISBN 978-0-470-57095-1.
  5. ^Rodwell, Victor (2015).Harper's illustrated Biochemistry. USA: McGraw-Hill. p. 176.ISBN 978-0-07-182537-5.
  6. ^Rodwell, Victor (2015).Harper's illustrated biochemistry, 13th edition. USA: McGraw-Hill. p. 204.ISBN 978-0-07-182537-5.
  7. ^Iwaki, Yoshimi; Sakai, Yusuke; Ochiai, Kenji; Umemura, Takashi; Sunden, Yuji (2014-03-01)."Enhancement of antibody production against rabies virus by uridine 5′-triphosphate in mice".Microbes and Infection.16 (3):196–202.doi:10.1016/j.micinf.2013.11.012.ISSN 1286-4579.PMID 24309427.
  8. ^Lamarca, Aloa; Gella, Alejandro; Martiañez, Tania; Segura, Mònica; Figueiro-Silva, Joana; Grijota-Martinez, Carmen; Trullas, Ramón; Casals, Núria (2014-06-06). Zegers, Mirjam M. (ed.)."Uridine 5′-Triphosphate Promotes In Vitro Schwannoma Cell Migration through Matrix Metalloproteinase-2 Activation".PLOS ONE.9 (6) e98998.Bibcode:2014PLoSO...998998L.doi:10.1371/journal.pone.0098998.ISSN 1932-6203.PMC 4048211.PMID 24905332.
Nucleic acid constituents
Nucleobase
Nucleoside
Ribonucleoside
Deoxyribonucleoside
Nucleotide
(Nucleoside monophosphate)
Ribonucleotide
Deoxyribonucleotide
Cyclic nucleotide
Nucleoside diphosphate
Nucleoside triphosphate
Receptor
(ligands)
P0 (adenine)
P1
(adenosine)
P2
(nucleotide)
P2X
(ATPTooltip Adenosine triphosphate)
P2Y
Transporter
(blockers)
CNTsTooltip Concentrative nucleoside transporters
ENTsTooltip Equilibrative nucleoside transporters
PMATTooltip Plasma membrane monoamine transporter
Enzyme
(inhibitors)
XOTooltip Xanthine oxidase
Others
Others
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