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5,6-Dihydro-5(α-thyminyl)thymine

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5,6-Dihydro-5(α-thyminyl)thymine
Names
IUPAC name 5--2,4(1H,3H)-pyrimidinedione
Other names 5-Thyminyl-5,6-dihydrothymine
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C10H12N4O4/c1-10(4-12-9(18)14-7(10)16)2-5-3-11-8(17)13-6(5)15/h3H,2,4H2,1H3,(H2,11,13,15,17)(H2,12,14,16,18)Key: RQDDFAKFBFKUBC-UHFFFAOYSA-N
SMILES
  • CC1(CNC(=O)NC1=O)CC2=CNC(=O)NC2=O
Properties
Chemical formula C10H12N4O4
Molar mass 252.230 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

5,6-Dihydro-5(α-thyminyl)thymine is a DNA pyrimidine dimer photoproduct produced when DNA in bacterial spores is exposed to ultraviolet light. In bacteria, this DNA base dimer deforms the structure of DNA, so endospore forming bacteria have an enzyme called spore photoproduct lyase that repairs this damage.

Natural production and repair of 5,6-dihydro-5(α-thyminyl)thymine

Laboratory synthesis

5,6-Dihydro-5(α-thyminyl)thymine can also be synthesized in a laboratory by reacting 5-hydroxymethyluracil and 6-aminothymine yielding 5,6-dihydro-6-imino-5-(α-thyminyl)thymine. When hydrogen is added in a reduction then 5,6-dihydro-5(α-thyminyl)thymine is the product.

References

  1. Varghese, A.J. (February 1970). "5-Thyminyl-5,6-dihydrothymine from DNA irradiated with ultraviolet light". Biochemical and Biophysical Research Communications. 38 (3): 484–490. doi:10.1016/0006-291x(70)90739-4. PMID 5462695.
  2. Moeller, Ralf; Douki, Thierry (2007). "UV-radiation-induced formation of DNA bipyrimidine photoproducts in Bacillus subtilis endospores and their repair during germination". International Microbiology. 1 (10): 39–46. doi:10.2436/20.1501.01.6.
  3. Bergstrom, Donald E.; Rash, Kenneth F. (1978). "Synthesis of a photoproduct from ultraviolet-irradiation of bacterial spores: 5,6-dihydro-5-(α-thyminyl)thymine". J. Chem. Soc., Chem. Commun. (7): 284. doi:10.1039/C39780000284.
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