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Thymidine

– Structure and properties: – Deoxythymidine is a nucleoside composed of deoxyribose and thymine. – It can be phosphorylated to form dTMP, dTDP, or dTTP. […]

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– Structure and properties:
– Deoxythymidine is a nucleoside composed of deoxyribose and thymine.
– It can be phosphorylated to form dTMP, dTDP, or dTTP.
– Deoxythymidine exists as white crystals or powder with a molecular weight of 242.229u.
– It is stable under standard temperature and pressure.
– Deoxythymidine is a naturally occurring compound in all living organisms and DNA viruses.

– Modified analogs:
– Iododeoxyuridine is a radiosensitizer.
– Azidothymidine (AZT) is used in HIV treatment.
– Radiolabeled thymidine is used in cell proliferation assays.
– Bromodeoxyuridine is used to detect proliferating cells.
– 5-Ethynyl-2´-deoxyuridine is used to assay DNA synthesis.

– Thymidine imbalance induces mutation and recombination:
– Excess thymidine availability increases mutation in bacteriophage T4.
– Thymidine deficiency also increases mutation.
– High thymidylate levels are mutagenic and recombinogenic.
– Starvation for thymidylate is recombinogenic but slightly mutagenic.

– References:
– Enzymatic Production of 5-Methyluridine by Erwinia carotovora AJ-2992.
– List of chemicals known or believed to be teratogens.
– Telbivudine (LdT) is used in chronic hepatitis B treatment.
– Stimulation of mutation in phage T4 by thymidine imbalance.
– Variation of mutation and recombination frequencies over a range of thymidylate concentrations.

– External links:
– Money.cnn.com article archive.
– Chembox image size adjustment.

Thymidine (Wikipedia)

Thymidine (symbol dT or dThd), also known as deoxythymidine, deoxyribosylthymine, or thymine deoxyriboside, is 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 G1/early S phase. The prefix deoxy- is often left out since there are no precursors of thymine nucleotides involved in RNA synthesis.

Thymidine
Skeletal formula of thymidine
Ball-and-stick model of the thymidine molecule
Names
IUPAC name
Thymidine
Systematic IUPAC name
1-[(2R,4S,5R)-4-Hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4(1H,3H)-dione
Other names
Deoxythymidine, Td, dT, 1-[(2R,4S,5R)-4-Hydroxy-5-(hydroxymethyl)tetrahydrofur-2-yl]-5-methyl-1,3-dihydropyrimidine-2,4-dione
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.000.065 Edit this at Wikidata
MeSH Deoxythymidine
UNII
  • InChI=1S/C10H14N2O5/c1-5-3-12(10(16)11-9(5)15)8-2-6(14)7(4-13)17-8/h3,6-8,13-14H,2,4H2,1H3,(H,11,15,16)/t6-,7+,8+/m0/s1 ☒N
    Key: IQFYYKKMVGJFEH-XLPZGREQSA-N ☒N
  • InChI=1/C10H14N2O5/c1-5-3-12(10(16)11-9(5)15)8-2-6(14)7(4-13)17-8/h3,6-8,13-14H,2,4H2,1H3,(H,11,15,16)/t6-,7+,8+/m0/s1
    Key: IQFYYKKMVGJFEH-XLPZGREQBQ
  • Cc1cn(c(=O)[nH]c1=O)[C@H]2C[C@@H]([C@H](O2)CO)O
Properties
C10H14N2O5
Molar mass 242.231 g·mol−1
Melting point 185 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Before the boom in thymidine use caused by the need for thymidine in the production of the antiretroviral drug azidothymidine (AZT), much of the world's thymidine production came from herring sperm. Thymidine occurs almost exclusively in DNA but it also occurs in the T-loop of tRNA.

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