Dihydrouracil

Structural formula
General
Surname	Dihydrouracil
other names	1,3-diazinane-2,4-dione; 5,6-dihydrouracil;
Molecular formula	C 4 H 6 N 2 O 2
External identifiers / databases
EC number	207-982-1
ECHA InfoCard	100.007.257
PubChem	649
ChemSpider	629
DrugBank	DB01849
Wikidata	Q409340
properties
Molar mass	114.10 g mol −1
Physical state	firmly
Melting point	279-281 ° C
safety instructions
GHS labeling of hazardous substances	no GHS pictograms
	no GHS pictograms
H and P phrases	H: no H-phrases
	P: no P-phrases
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Dihydrouracil is a heterocyclic organic compound with a hydrogenated pyrimidine backbone and two carbonyl groups in positions 2 and 4. The nucleoside of Dihydrouracil is dihydrouridine (D, UH ₂ , Uh) occurs in the t RNA . Like uracil, it forms a base pair with adenine .

Emergence

Uracil is hydrogenated in nucleosides by the dihydropyrimidine dehydrogenase to dihydrouracil.

+ NADPH / H ⁺ + NADP ⁺

{\ displaystyle \ rightleftharpoons}

Dihydrouracil is a solid, with a melting temperature of 279-281 ° C.

It forms the base pairing to adenine with two hydrogen bonds in the RNA via the 4-oxo group and the N – H group .

Structural formula of an AD base pair

It gives its name to the dihydrouracil loop in the tRNA.

↑ ^a ^b ^c ^d data sheet dihydrouracil from Sigma-Aldrich , accessed on November 22, 2013 ( PDF ).
↑ H. Shi, PB Moore : "The crystal structure of yeast phenylalanine tRNA at 1.93 Å resolution: a classic structure revisited", in: RNA , 2000 , 6 (8), pp. 1091–1105 ( PMC 1369984 (free full text) ; PMID 10943889 ).

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

Commons : Dihydrouracil - Collection of images, videos and audio files

Entry for Dihydrouracil in the Human Metabolome Database (HMDB) , accessed November 8, 2013.