Thymine

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For the similarly-spelled vitamin compound, see Thiamine
Thymine
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. Also known as 5-methyluracil a pyrimidine nucleobase. As the name implies, 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. </td></tr></table>

Thymine could also be a target for actions of 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 inhibit DNA synthesis in actively dividing cells.

References

See Also


External links



<tr bgcolor="#ccccff"><td colspan="3" align="center">
v  d  e
Major families of biochemicals</td></tr><tr><td colspan="3" style="text-align: center;">Peptides | Amino acids | Nucleic acids | Carbohydrates | Nucleotide sugars | Lipids | Terpenes | Carotenoids | Tetrapyrroles | Enzyme cofactors | Steroids | Flavonoids | Alkaloids | Polyketides | Glycosides</td></tr><tr bgcolor="pink"><td style="white-space: nowrap; width: 10%; color: pink;">Analogues of nucleic acids:</td><td align="center">Types of Nucleic Acids</td><td style="white-space: nowrap; width: 10%; color: pink;">Analogues of nucleic acids:</td></tr>
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 | tRNA | rRNA | gRNA | miRNA | ncRNA | piRNA | shRNA | siRNA | snRNA | snoRNA
Deoxyribonucleic acids: DNA | mtDNA | cDNA
Nucleic acid analogues: GNA | LNA | PNA | TNA | morpholino
Cloning vectors: plasmid | cosmid | fosmid | phagemid | BAC | YAC | HAC
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