Uridine diphosphate

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Structural formula
Structure of uridine diphosphate
General
Surname Uridine diphosphate
other names
  • Uridine 5'-trihydrogen diphosphate
  • UDP
Molecular formula C 9 H 14 N 2 O 12 P 2
External identifiers / databases
CAS number 58-98-0
EC number 200-409-6
ECHA InfoCard 100,000,372
PubChem 6031
DrugBank DB03435
Wikidata Q412593
properties
Molar mass 404.16 g mol −1
safety instructions
GHS hazard labeling
no classification available
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Uridine diphosphate (UDP for short) is a chemical compound from the group of nucleotides ( ribonucleotides ) which is derived from uridine . It is an ester of the diphosphoric acid with the nucleoside uridine and consists of a pyrophosphate , the sugar ribose and the nucleobase uracil .

Biological importance

Uridine diphosphate is the most important uridine nucleotide mainly involved in carbohydrate metabolism and acts as a coenzyme in glycosidation .

Uridine diphosphate results from a catalyzed reaction of glycogenin . This catalyzes the addition of glucose to itself by binding the first UDP-glucose , formed from UTP and glucose, to the Tyr-194 residue of its active center , producing uridine diphosphate.

Glycogenin + +UDP glucose   
   Glc-glycogeninUDP

UDP is also the starting material for the synthesis of dTTP ( deoxythymidine triphosphate ), which is used for DNA synthesis. First of all, UDP is converted to dUDP by the ribonucleotide reductase . After dephosphorylation to the dUMP, this is methylated to the dTMP by the thymidylate synthase (see figure on the right). N 5 , N 10 -methylene tetrahydrofolate acts as the methyl group donor . The resulting dTMP is phosphorylated to triphosphate (dTTP) and can be used for DNA synthesis.

Synthesis of dTMP ( 1b ) from dUMP ( 1a ). During the reaction, N 5 , N 10 -methylene tetrahydrofolate ( 4 ) is converted to 7,8-dihydrofolate ( 2 ), which catalyzes the thymidylate synthase ( EC  2.1.1.45 ) ( A ). This is under NADPH -consumption to tetrahydrofolate ( 3 ) through the dihydrofolate reductase ( EC  1.5.1.3 ) ( B reduced). The serine hydroxymethyl transferase ( EC  2.1.2.1 ) ( C ) finally regenerates N 5 , N 10 -methylene tetrahydrofolate with consumption of serine .

Related links

Individual evidence

  1. ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
  2. ^ Roche Lexicon Medicine: Uridine diphosphate .