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Thymine

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Thymine

Thymine
IUPAC name

5-Methylpyrimidine-2,4(1H,3H)-dione

Other names

5-methyluracil

Identifiers
CAS number  YesY
PubChem
ChemSpider  N
UNII  YesY
MeSH
ChEBI  N
ChEMBL  N
Jmol-3D images Image 1
Properties
Molecular formula C5H6N2O2
Molar mass 126.11 g mol−1
Density 1.23 g cm−3 (calculated)
Melting point 316 to 317 °C (601 to 603 °F; 589 to 590 K)
Boiling point 335 °C (635 °F; 608 K) (decomposes)
Acidity (pKa) 9.7
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N   YesY/N?)

Thymine (T, Thy) is one of the four nucleobases in the nucleic acid of DNA that are represented by the letters G–C–A–T. The others are adenine, guanine, and cytosine. Thymine is also known as 5-methyluracil, a pyrimidine nucleobase. In RNA, thymine is replaced by the nucleobase uracil. Thymine was first isolated (from calves' thymus glands) in 1893 by Albrecht Kossel and Albert Neumann.[1]

Derivation

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, thus 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 [2]

Thymine is a nuclear base.

See also

References

  1. ^ Albrecht Kossel and Albert Neumann (1893) "Ueber das Thymin, ein Spaltungsproduct der Nucleïnsäure" (On thymine, a cleavage product of nucleic acid), Berichte der Deutschen Chemischen Gesellschaft zu Berlin, 26 : 2753-2756. From p. 2754: "Wir bezeichnen diese Substanz als Thymin." (We designate this substance as "thymine" [because it was initially obtained from the thymus glands of calves].)
  2. ^ Hofreiter M., Serre D., Poinar H.N., Kuch M., and Paabo S. Nature Reviews Genetics (2001) 2:353.

External links

  • Thymine MS Spectrum
  • Infoplease Encyclopedia
  • Science Aid: DNA Structure and Replication
Nucleic acid constituents
Nucleobase
Nucleoside
Ribonucleoside
Deoxyribonucleoside
Nucleotide
(Nucleoside monophosphate)
Ribonucleotide
Deoxyribonucleotide
Cyclic nucleotide
Nucleoside diphosphate
Nucleoside triphosphate
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