Thymidine


Thymidine
Thymidine
Identifiers
CAS number 50-89-5 YesY
PubChem 1134
UNII VC2W18DGKR N
DrugBank DB04485
MeSH Thymidine
ChEMBL CHEMBL52609 N
Jmol-3D images Image 1
Properties
Molecular formula C10H14N2O5
Molar mass 242.23 g mol−1
 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Thymidine (more precisely called deoxythymidine; can also be labelled deoxyribosylthymine, and thymine deoxyriboside) is a chemical compound, more precisely a pyrimidine deoxynucleoside. Deoxythymidine is the DNA nucleoside T, which pairs with deoxyadenosine (A) in double-stranded DNA. In cell biology it is used to synchronize the cells in S phase.

Before the boom in thymidine use caused by the need for thymidine for the production of the antiretroviral drug azidothymidine (AZT), much of the world's thymidine production came from herring sperm.[1] Thymidine occurs almost exclusively in DNA but also occurs in the T-loop of tRNA.

Contents

Structure and properties

In its composition, deoxythymidine is a nucleoside composed of deoxyribose (a pentose sugar) joined to the pyrimidine base thymine.

Deoxythymidine can be phosphorylated with one, two or three phosphoric acid groups, creating respectively dTMP, dTDP or dTTP (deoxythymidine mono- di- or triphosphate).

It exists in solid form as small white crystals or white crystalline powder, has a molecular weight of 242.229 u, and has a melting point of 185 °C. The stability of deoxythymidine under standard temperature and pressure (STP) is very high.

Deoxythymidine is non-toxic and as part of one of the four nucleotides in DNA it is a naturally occurring compound that exists in all living organisms and DNA viruses. RNA has uridine (uracil joined to ribose) instead. Uracil is chemically very similar to thymine, the latter being 5-methyluracil. Since thymine nucleotides are precursors of DNA, not RNA, the prefix "deoxy" is often left out, i.e., deoxythymidine is often just called thymidine.

Thymidine is listed as a chemical teratogen.[2]

Modified analogs of thymidine

Iododeoxyuridine is a radiosensitizer and increases the amount of DNA damage received from ionizing radiation.

Azidothymidine (AZT) - used in the treatment of HIV infection. AZT inhibits the process of reverse transcription, a critical step in the viral life cycle.

Tritiated thymidine is commonly used in cell proliferation assays. The thymidine is incorporated into dividing cells and the level of this incorporation, measured using a liquid scintillation counter, is proportional to the amount of cell proliferation.

Bromodeoxyuridine (BrdU) is another thymidine analog that is often used for the detection of proliferating cells in living tissues.

References

  1. ^ Makoto Ishii, Hideyuki Shirae, Kenzo Yokozeko, Enzymatic Production of 5-Methyluridine from Purine Nucleosides and Thymine by Erwinia carotovora AJ-2992, Agricultural and Biological Chemistry 
  2. ^ The following list of chemicals known or believed to be teratogens is drawn primarily from Dangerous Properties of Industrial Materials, 7th Ed., by N. Irving Sax and Richard J. Lewis.

External links


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Look at other dictionaries:

  • thymidine — n. f. BIOCHIM Nucléoside constitué par l association de la thymine et d un pentose, le ribose. (Son dérivé, la thymidine phosphate, est un constituant spécifique de l acide désoxyribonucléique.) …   Encyclopédie Universelle

  • thymidine — thymidine. См. тимидин. (Источник: «Англо русский толковый словарь генетических терминов». Арефьев В.А., Лисовенко Л.А., Москва: Изд во ВНИРО, 1995 г.) …   Молекулярная биология и генетика. Толковый словарь.

  • thymidine — [thī′mə dēn΄, thī′mədin] n. [< THYMINE + ID(E) + INE3] a crystalline nucleoside, C10H14N2O5, one of the basic components of DNA: used chiefly in biochemical research …   English World dictionary

  • Thymidine — Désoxythymidine Désoxythymidine Schéma de la désoxythymidine Général Synonymes thymidine …   Wikipédia en Français

  • thymidine — 1 (2 Deoxyribosyl)thymine; one of the four major nucleosides in DNA (the others being deoxyadenosine, deoxycytidine, and deoxyguanosine). SYN: deoxythymidine, thymine deoxyribonucleoside. t. phosphorylase phosphorylase that catalyzes the… …   Medical dictionary

  • thymidine — timidinas statusas T sritis chemija apibrėžtis nukleozidas santrumpa( os) Thd, dThd atitikmenys: angl. deoxythymidine; thymidine rus. дезокситимидин; тимидин ryšiai: sinonimas – deoksitimidinas sinonimas – 1 β D 2 deoksi D ribofuranoziltimidinas …   Chemijos terminų aiškinamasis žodynas

  • thymidine — noun Etymology: thymine + idine Date: 1912 a nucleoside C10H14N2O5 that is composed of thymine and deoxyribose and occurs as a structural part of DNA …   New Collegiate Dictionary

  • thymidine — Term that is always used in practice for the nucleoside thymine deoxyriboside; not the riboside which naming of the other nucleosides might lead one to expect …   Dictionary of molecular biology

  • thymidine — /thuy mi deen /, n. Biochem. a nucleoside, C10H14N2O5, containing thymine and deoxyribose, that is a constituent of DNA. [b. THYMINE and IDE] * * * …   Universalium

  • thymidine — noun The nucleoside consisting of a combination of deoxyribose and thymine …   Wiktionary


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