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5,6-Dihydro-5(α-thyminyl)thymine

Chemical compound From Wikipedia, the free encyclopedia

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]

Natural production and repair of 5,6-dihydro-5(α-thyminyl)thymine
Quick facts Names, Identifiers ...
5,6-Dihydro-5(α-thyminyl)thymine
Names
Preferred IUPAC name
5-[(5-Methyl-2,4-dioxo-1,3-diazinan-5-yl)methyl]pyrimidine-2,4(1H,3H)-dione
Other names
5-Thyminyl-5,6-dihydrothymine
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
UNII
  • 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
  • CC1(CNC(=O)NC1=O)CC2=CNC(=O)NC2=O
Properties
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).
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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]

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