Dihydrouracil

Dihydrouracil
Names
Preferred IUPAC name
1,3-Diazinane-2,4-dione
Other names
Dihydropyrimidine-2,4(1H,3H)-dione
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.007.257
MeSH Dihydrouracil
PubChem CID
UNII
CompTox Dashboard (EPA)
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 checkY☒N ?)
Infobox references

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

2D representation of the chemical structure of uracil .
uracil
+ NADH
 
 
H+
 
Reversible left-right reaction arrow with minor forward substrate(s) from top left and minor reverse product(s) to bottom left
H+
 
 
2D representation of the chemical structure of dihydrouracil .
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.


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