Thymine

Thymine

Chembox new
ImageFile1 = Thymine.png ImageSize1 = 150px
ImageFileL2 = Thymine-3D-balls.png ImageSizeL2 = 100px
ImageFileR2 = Thymine-3D-vdW.png ImageSizeR2 = 100px
ImageFile =
ImageSize =
IUPACName = 5-Methylpyrimidine-2,4(1"H",3"H")-dione
OtherNames =
Section1 = Chembox Identifiers
CASNo = 65-71-4
PubChem =
SMILES = CC1=CNC(=O)NC1=O
MeSHName = Thymine
Section2 = Chembox Properties
Formula = C5H6N2O2
MolarMass = 126.11334 g/mol
Appearance =
Density =
MeltingPt = 316 - 317 °C
BoilingPt =
Section3 = Chembox Hazards
Solubility =
MainHazards =
FlashPt =
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Thymine is one of the four bases in the nucleic acid of DNA that make up the letters ATGC. The others are adenine, guanine, and cytosine. Thymine (T) always pairs with adenine. Thymine is also known as 5-methyluracil, a pyrimidine nucleobase. As the name suggests, thymine may be derived by methylation of uracil at the 5th carbon. In RNA, thymine is replaced with uracil in most cases. In DNA, thymine(T) binds to adenine (A) via two hydrogen bonds to assist in stabilizing the nucleic acid structures.

Thymine combined with deoxyribose creates the nucleoside deoxythymidine, which is synonymous with the term thymidine. Thymidine can be phosphorylated with one, two, or three phosphoric acid groups, creating, respectively, TMP, TDP, or TTP (thymidine mono-, di-, or triphosphate).

One of the common mutations of DNA involves two adjacent thymines or cytosine, which, in presence of ultraviolet light, may form thymine dimers, causing "kinks" in the DNA molecule that inhibit normal function.

Thymine could also be a target for actions of 5-fluorouracil (5-FU) in cancer treatment. 5-FU can be a metabolic analog of thymine (in DNA synthesis) or uracil (in RNA synthesis). Substitution of this analog inhibits DNA synthesis in actively-dividing cells.

Thymine bases are frequently oxidized to hydantoins over time after the death of an organism [Hofreiter M., Serre D., Poinar H.N., Kuch M., and Paabo S. "Nature Reviews Genetics" (2001) 2:353. ] .

References

ee also

*deoxyribose
*pyrimidine
*nucleobase
*deoxythymidine

*uracil

External links

* [http://www.compchemwiki.org/index.php?title=Thymine Computational Chemistry Wiki]
* [http://www.infoplease.com/ce6/sci/A0848663.html Infoplease Encyclopedia]
* [http://www.scienceaid.co.uk/biology/genetics2/dna.html Science Aid: DNA Structure and Replication ]


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