View source for 5,6-Dihydro-5(α-thyminyl)thymine

{{Chembox
|ImageFile = 5,6-dihydro-5(α-thyminyl)thymine.svg
|ImageSize = 200px
|IUPACName = 5-[(5-Methyl-2,4-dioxohexahydro-5-pyrimidinyl)methyl]-2,4(1''H'',3''H'')-pyrimidinedione
|OtherNames = 5-Thyminyl-5,6-dihydrothymine
|Section1 = {{Chembox Identifiers
| index1_label=with sugars
| CASNo = 28100-77-8
| PubChem = 161592
| ChEBI1 = 139518
| ChemSpiderID = 141931
| StdInChI = 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)
| StdInChIKey = RQDDFAKFBFKUBC-UHFFFAOYSA-N
| SMILES = CC1(CNC(=O)NC1=O)CC2=CNC(=O)NC2=O
}}
|Section2={{Chembox Properties
|C=10|H=12|N=4|O=4
}}
}}
'''5,6-Dihydro-5(α-thyminyl)thymine''' is a DNA [[pyrimidine dimer]] [[photochemistry|photoproduct]] produced when [[DNA]] in [[bacterial spore]]s is exposed to ultraviolet light.<ref>{{cite journal |last1=Varghese |first1=A.J. |title=5-Thyminyl-5,6-dihydrothymine from DNA irradiated with ultraviolet light |journal=Biochemical and Biophysical Research Communications |date=February 1970 |volume=38 |issue=3 |pages=484–490 |doi=10.1016/0006-291x(70)90739-4 |pmid=5462695 }}</ref>  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.<ref>{{cite journal |last1=Moeller |first1=Ralf |last2=Douki |first2=Thierry |title=UV-radiation-induced formation of DNA bipyrimidine photoproducts in Bacillus subtilis endospores and their repair during germination |journal=International Microbiology |date=2007 |volume=1 |issue=10 |pages=39–46 |doi=10.2436/20.1501.01.6}}</ref>
[[Image:Spore photoproduct lyase (reaction diagram).png|thumb|left|300px|Natural production and repair of 5,6-dihydro-5(α-thyminyl)thymine]]{{clear-left}}
==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.<ref>{{cite journal |last1=Bergstrom |first1=Donald E. |last2=Rash |first2=Kenneth F. |title=Synthesis of a photoproduct from ultraviolet-irradiation of bacterial spores: 5,6-dihydro-5-(α-thyminyl)thymine |journal=J. Chem. Soc., Chem. Commun. |date=1978  |issue=7 |pages=284 |doi=10.1039/C39780000284}}</ref>
==References==
{{Reflist}}
{{DEFAULTSORT:Dihydro-5(α-thyminyl)thymine, 5, 6-}}
[[Category:Pyrimidinediones]]
[[Category:Dimers (chemistry)]]