Dihydrouracil

Dihydrouracil

Names
Preferred IUPAC name 1,3-Diazinane-2,4-dione
Other names Dihydropyrimidine-2,4(1H,3H)-dione
Identifiers
CAS Number	504-07-4  Y
3D model (JSmol)	Interactive image
ChemSpider	629  N
ECHA InfoCard	100.007.257
MeSH	Dihydrouracil
PubChem CID	649
UNII	016FR52RU5  Y
CompTox Dashboard (EPA)	DTXSID7060122
InChI InChI=1S/C4H6N2O2/c7-3-1-2-5-4(8)6-3/h1-2H2,(H2,5,6,7,8) N Key: OIVLITBTBDPEFK-UHFFFAOYSA-N N InChI=1/C4H6N2O2/c7-3-1-2-5-4(8)6-3/h1-2H2,(H2,5,6,7,8) Key: OIVLITBTBDPEFK-UHFFFAOYAM
SMILES C1CNC(=O)NC1=O
Properties
Chemical formula	C4H6N2O2
Molar mass	114.10264
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N  verify  (what is  YN ?) Infobox references

Dihydrouracil is an intermediate in the catabolism of uracil. ^[1] The enzyme dihydrouracil dehydrogenase (NAD+) converts uracil to dihydrouracil:

uracil

+ NADH

 

 

H⁺

 

H⁺

 

 

dihydrouracil

+ NAD⁺

 

The enzyme uses reduced nicotinamide adenine dinucleotide (NADH) as its cofactor. ^{[2] [3]}

Dihydrouracil is the base present in the nucleoside dihydrouridine. ^[4]

See also

• Dihydrouracil oxidase
• Dihydropyrimidinase

References

1. Nakamura, A; Kikuchi, K; Ohishi, T; Masuike, T (March 2004). "[Assay method for uracil, dihydrouracil, 5-fluorouracil and 5-fluoro-5, 6-dihydrouracil by high-performance liquid chromatography]". Gan to Kagaku Ryoho. Cancer & Chemotherapy. 31 (3): 381–6. PMID   15045945.
2. Campbell LL (August 1957). "Reductive degradation of pyrimidines. III. Purification and properties of dihydrouracil dehydrogenase". The Journal of Biological Chemistry. 227 (2): 693–700. doi: 10.1016/S0021-9258(18)70749-7 . PMID   13462991.
3. West, Thomas P. (2001). "Pyrimidine base catabolism in Pseudomonas putida biotype B". Antonie van Leeuwenhoek. 80 (2): 163–167. doi:10.1023/A:1012275512136. PMID   11759049.
4. Dalluge, J.; Hashizume, T.; Sopchik, A. E.; McCloskey, J. A.; Davis, D. R. (1996). "Conformational flexibility in RNA: The role of dihydrouridine". Nucleic Acids Research. 24 (6): 1073–1079. doi:10.1093/nar/24.6.1073. PMC   145759 . PMID   8604341.