Thymine

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For the similarly-spelled vitamin compound, see Thiamine

Thymine
Image:Thymine.png
IUPAC name	5-Methylpyrimidine-2,4(1H,3H)-dione
Identifiers
CAS number	65-71-4
MeSH	Thymine
SMILES	CC1=CNC(=O)NC1=O
Properties
Molecular formula	C5H6N2O2
Molar mass	126.11334 g/mol
Melting point	316 - 317 °C
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

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^[1].

[edit] References

[edit] See also

deoxyribose pyrimidine nucleobase deoxythymidine

uracil

[edit] External links

• Computational Chemistry Wiki
• Infoplease Encyclopedia
• Science Aid: DNA Structure and Replication

v • d • e Major families of biochemicals
Peptides | Amino acids | Nucleic acids | Carbohydrates | Nucleotide sugars | Lipids | Terpenes | Carotenoids | Tetrapyrroles | Enzyme cofactors | Steroids | Flavonoids | Alkaloids | Polyketides | Glycosides
Analogues of nucleic acids:	Types of Nucleic Acids	Analogues of nucleic acids:
Nucleobases:	Purine (Adenine, Guanine) | Pyrimidine (Uracil, Thymine, Cytosine)
Nucleosides:	Adenosine/Deoxyadenosine | Guanosine/Deoxyguanosine | Uridine | Thymidine | Cytidine/Deoxycytidine
Nucleotides:	monophosphates (AMP, GMP, UMP, CMP) | diphosphates (ADP, GDP, UDP, CDP) | triphosphates (ATP, GTP, UTP, CTP) | cyclic (cAMP, cGMP, cADPR)
Deoxynucleotides:	monophosphates (dAMP, dGMP, TMP, dCMP) | diphosphates (dADP, dGDP, TDP, dCDP) | triphosphates (dATP, dGTP, TTP, dCTP)
Ribonucleic acids:	RNA | mRNA (pre-mRNA/hnRNA) | tRNA | rRNA | gRNA | miRNA | ncRNA | piRNA | shRNA | siRNA | snRNA | snoRNA
Deoxyribonucleic acids:	DNA | cDNA | gDNA | msDNA | mtDNA
Nucleic acid analogues:	GNA | LNA | PNA | TNA | morpholino
Cloning vectors:	phagemid | plasmid | lambda phage | cosmid | P1 phage | fosmid | BAC | YAC | HAC

ar:ثايمين

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