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Thymidine



Thymidine
Identifiers
CAS number 50-89-5
PubChem 1134
MeSH Thymidine
SMILES CC1=CN(C(=O)NC1=O)C2CC(C(O2)CO)O
Properties
Molecular formula C10H14N2O5
Molar mass 242.229
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)
Infobox disclaimer and 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.

Additional recommended knowledge

Structure and properties

In its composition, deoxythymidine is 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 ((deoxy)thymidine 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.

Modified analogs of thymidine

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

Azidothymidine (AZT) - the treatment against HIV, which blocks the process of reverse transcription from the virus's RNA into DNA to be incorporated into the host cell.

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.



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
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Thymidine". A list of authors is available in Wikipedia.
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