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a nucleoside component of DNA; composed of thymine and deoxyribose (同)thymidine

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/09/14 05:47:27」(JST)

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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 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.

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.

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.

References

^ 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.

External links

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

UpToDate Contents

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Related Pictures

★リンクテーブル★

リンク元	「ヌクレオチド」「チミジン」「deoxythymidine」「サイミジン」
拡張検索	「deoxythymidine monophosphate」「deoxythymidine triphosphate」「thymidine triphosphate」「thymidine monophosphate」

「ヌクレオチド」

Thymidine
Identifiers
CAS Registry Number	50-89-5
ChEMBL	ChEMBL52609
ChemSpider	5585
DrugBank	DB04485
	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 ; Key: IQFYYKKMVGJFEH-XLPZGREQSA-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 ;
IUPHAR/BPS	4718
Jmol-3D images	Image
MeSH	Thymidine
PubChem	1134
	SMILES Cc1cn(c(=O)[nH]c1=O)[C@H]2C[C@@H]([C@H](O2)CO)O ;
UNII	VC2W18DGKR
Properties
Chemical formula	C10H14N2O5
Molar mass	242.23 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references

　　[★]

英: nucleotide
関: ヌクレオチド

核酸塩基+糖+リン酸
ヌクレオシドの糖の部分に1個以上のリン酸基がエステル結合した物質

生合成

De novo pathway

phosphoribosyl pyrophosphate + uridylate→…→nucleptode

アミノプテリンが途中の合成系路を阻害する　←　モノクローナル抗体の作成における選抜に利用される (関：HAT培地)

Salvage pathway]

2通りの経路がある
1. thymidine→…→nucleptode

thymidine kinase(TK)が触媒

2. hypoxanthine→…→nucleptode

hupoxanthine guanine phosphoribosyl transferase(HGPRT)が関与

「チミジン」

　　[★]

英: thymidine, dThd
同: 1-(2-デオキシ-β-D-リボフラノシル)-5-メチルウラシル 1-(2-deoxy-β-D-ribofuranosyl)-5-methyluracil、デオキシチミジン deoxythymidine dT、チミンデオキシリボシドthymine deoxyriboside]] TdR
関: チミン

「deoxythymidine」

　　[★]

チミジン、デオキシチミジン

関: dT、thymidine

「サイミジン」

　　[★]

英: thymidine
関: チミジン、デオキシチミジン

「deoxythymidine monophosphate」

　　[★]

チミジン一リン酸、デオキシチミジン一リン酸

関: dTMP、thymidine monophosphate、thymidylate

「deoxythymidine triphosphate」

　　[★]

チミジン三リン酸、デオキシチミジン三リン酸

関: dTTP、thymidine triphosphate、TTP

「thymidine triphosphate」

　　[★]

チミジン三リン酸

関: deoxythymidine triphosphate、dTTP、TTP

「thymidine monophosphate」

　　[★] チミジン一リン酸 TMP

[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.

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案内

案内

thymidine