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Thymidine

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Chemical compound

Thymidine

Names

Preferred 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

CAS Number

50-89-5 Y

3D model (JSmol)

Interactive image

ChEMBL

ChEMBL52609 N

ChemSpider

5585 N

DrugBank

DB04485 N

ECHA InfoCard

100.000.065

IUPHAR/BPS

4718

MeSH

Thymidine

PubChem CID

1134

UNII

VC2W18DGKR N

CompTox Dashboard (EPA)

DTXSID5023661

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InChI

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

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SMILES

Cc1cn(c(=O)[nH]c1=O)[C@H]2C[C@@H]([C@H](O2)CO)O

Properties

Chemical formula

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).

N verify (what is YN ?)

Infobox references

Chemical compound

Thymidine (deoxythymidine; other names deoxyribosylthymine, 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.

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.[1] Thymidine occurs almost exclusively in DNA but it also occurs in the T-loop of tRNA.

Contents

1 Structure and properties

2 Modified analogs

3 Thymidine imbalance induces mutation and recombination

4 References

5 External links

Structure and properties[edit]

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 dTMP (deoxythymidine monophosphate), dTDP, or dTTP (for the di- and tri- phosphates, respectively).

It exists in solid form as small white crystals or white crystalline powder. It has a molecular weight of 242.229 u and 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 nucleosides in DNA it is a naturally occurring compound that exists in all living organisms and DNA viruses. Instead of thymidine, RNA contains uridine (uracil joined to ribose). Uracil is chemically very similar to thymine, which is also known as 5-methyluracil. Since thymine nucleotides are precursors of DNA (but 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[edit]

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.

Radiolabeled thymidine (TdR), such as tritiated thymidine (3H-TdR), 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. For example, lymphocyte proliferation can be measured this way in lymphoproliferative disorders.

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

5-Ethynyl-2´-deoxyuridine (EdU) is a thymidine analog which is incorporated into the DNA of dividing cells and is used to assay DNA synthesis in cell culture or living tissues. It can be visualized by covalently binding a fluorescent azide using click chemistry, which is less harsh than the conditions used to expose the epitope for BrdU antibodies.

Edoxudine is an antiviral drug.

Thymidine imbalance induces mutation and recombination[edit]

During growth of bacteriophage T4, an excess of thymidine availability increases mutation.[3][4] A deficiency of thymidine during growth also increases mutation.[3] A thymidylate auxotroph of the diploid yeast Saccharomyces cerevisiae was grown under conditions in which thymidyate levels varied from excess to depletion.[5] High levels of thymidylate were observed to be mutagenic and recombinogenic, whereas starvation for thymidylate was recombinogenic but only slightly mutagenic.

References[edit]

^ 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

^ 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.

^ Jump up to: a b Bernstein C, Bernstein H, Mufti S, Strom B. Stimulation of mutation in phage T 4 by lesions in gene 32 and by thymidine imbalance. Mutat Res. 1972 Oct;16(2):113-9. doi: 10.1016/0027-5107(72)90171-6. PMID: 4561494

^ DeVries JK, Wallace SS. Reversion of bacteriophage T4rII mutants by high levels of pyrimidine deoxyribonucleosides. Mol Gen Genet. 1982;186(1):101-5. doi: 10.1007/BF00422919. PMID: 7050620

^ Eckardt F, Kunz BA, Haynes RH. Variation of mutation and recombination frequencies over a range of thymidylate concentrations in a diploid thymidylate auxotroph. Curr Genet. 1983 Sep;7(5):399-402. doi: 10.1007/BF00445881. PMID: 24173422

External links[edit]

http://money.cnn.com/magazines/fortune/fortune_archive/1990/11/05/74308/index.htm

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t

e

Nucleic acid constituents

Nucleobase

Purine

Adenine

Guanine

Hypoxanthine

Xanthine

Purine analogue

Pyrimidine

Uracil

Thymine

Cytosine

Pyrimidine analogue

Unnatural base pair (UBP)

Nucleoside

Ribonucleoside

Adenosine

Guanosine

5-Methyluridine

Uridine

5-Methylcytidine

Cytidine

Pseudouridine

Inosine

N6-Methyladenosine

Xanthosine

Wybutosine

Deoxyribonucleoside

Deoxyadenosine

Deoxyguanosine

Thymidine

Deoxyuridine

Deoxycytidine

Deoxyinosine

Deoxyxanthosine

Nucleotide
(Nucleoside monophosphate)

Ribonucleotide

AMP

GMP

m5UMP

UMP

CMP

IMP

XMP

Deoxyribonucleotide

dAMP

dGMP

dTMP

dUMP

dCMP

dIMP

dXMP

Cyclic nucleotide

cAMP

cGMP

c-di-GMP

c-di-AMP

cADPR

cGAMP

Nucleoside diphosphate

ADP

GDP

m5UDP

UDP

CDP

dADP

dGDP

dTDP

dUDP

dCDP

Nucleoside triphosphate

ATP

GTP

m5UTP

UTP

CTP

ITP

XTP

dATP

dGTP

dTTP

dUTP

dCTP

dITP

dXTP

Retrieved from "https://en.wikipedia.org/w/index.php?title=Thymidine&oldid=1021857203"

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This page was last edited on 7 May 2021, at 01:59 (UTC).

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