5,6-Dihydro-5(α-thyminyl)thymine

5,6-Dihydro-5(α-thyminyl)thymine
Names
	IUPAC name 5-[(5-Methyl-2,4-dioxohexahydro-5-pyrimidinyl)methyl]-2,4(1H,3H)-pyrimidinedione
	Other names 5-Thyminyl-5,6-dihydrothymine
Identifiers
CAS Number	28100-77-8;
3D model (JSmol)	Interactive image;
ChEBI	with sugars: CHEBI:139518;
ChemSpider	141931;
PubChem CID	161592;
CompTox Dashboard (EPA)	DTXSID10950840 ;
	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−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

5,6-Dihydro-5(α-thyminyl)thymine is a DNA pyrimidine dimer photoproduct produced when DNA in bacterial spores is exposed to ultraviolet light.^[1] 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.^[2]

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.^[3]

References

^ 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.
^ 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.
^ 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.

[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.

[1]

[2]

[3]