Uridine monophosphate

Structural formula
General
Surname	5′-uridylic acid ( IUPAC )
Molecular formula	C 9 H 13 N 2 O 9 P
External identifiers / databases
EC number	200-408-0
ECHA InfoCard	100,000,371
PubChem	1172
Wikidata	Q414932
properties
Molar mass	324.18 g mol −1
Physical state	firmly
Melting point	202 ° C (decomposition)
solubility	easily soluble in water; soluble in methanol ;
safety instructions
GHS hazard labeling ; no classification available
GHS hazard labeling ; no classification available
Toxicological data	> 1 g kg −1 ( LD 50 , mouse , ip )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

As uridine monophosphate , or uridylate refers to the monophosphate of uridine . It belongs to the group of nucleotides and is present in all living things. Uridine monophosphate is the most important intermediate in pyrimidine biosynthesis . All other pyrimidine nucleotides are formed from UMP, and it is formed again when they are broken down.

If the phosphate residue is bound to deoxyribose , one speaks of deoxyuridine monophosphate or deoxyuridylate (dUMP), which is an intermediate product in the biosynthesis of the DNA nucleotide deoxythymidine triphosphate (dTTP).

Biosynthesis and function

Origin of the individual atoms in UMP in de novo synthesis (red: PRPP , green: aspartate ; black: hydrogen carbonate ; blue: amino group from glutamine.)

In addition to dephosphorylation of UDP and UTP, UMP is obtained by several synthetic pathways in the metabolism. The main route, de novo synthesis , begins with glutamine and carbamoyl phosphate and proceeds via orotate to orotidine-5'-monophosphate (OMP), which is converted to UMP with the aid of the enzyme orotidine-5'-phosphate decarboxylase .

Another possibility is the phosphorylation of uridine using uridine kinase . It can also be obtained directly from uracil , when it reacts with phosphoribosyl pyrophosphate (PRPP), which is catalyzed by uracil phosphoribosyl transferase .

Finally, UMP arises as a by-product in the metabolism of some bacteria , in the biosynthesis of peptidoglycans ( EC 2.7.8.6 , EC 2.7.8.13 etc.) and in the breakdown of UDP-glucose ( EC 3.6.1.45 ).

Web links

Wikibooks: Biochemistry and Pathobiochemistry: Pyrimidine Metabolism - Learning and Teaching Materials

Individual evidence

↑ ^a ^b ^c M. Lide, DR Lide: CRC Handbook of Chemistry and Physics . 87th edition, pp. 3-56, CRC Press, 1998, ISBN 978-0-8493-0594-8
↑ ^a ^b Entry on uridine monophosphate in the ChemIDplus database of the United States National Library of Medicine (NLM)
↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
^ Annals of the New York Academy of Sciences . Vol. 60, Pg. 251, 1954.

[lide-1] M. Lide, DR Lide: CRC Handbook of Chemistry and Physics . 87th edition, pp. 3-56, CRC Press, 1998, ISBN 978-0-8493-0594-8

[chemid-2] Entry on uridine monophosphate in the ChemIDplus database of the United States National Library of Medicine (NLM)

[NV-3] This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.

[4] Annals of the New York Academy of Sciences . Vol. 60, Pg. 251, 1954.