関: N、nucleosidic

WordNet

a glycoside formed by partial hydrolysis of a nucleic acid
the 14th letter of the Roman alphabet (同)n

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nitrogenの化学記号

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2013/02/12 14:30:00」(JST)

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Nitrogenous base	Ribonucleoside	Deoxyribonucleoside
Adenine	Adenosine A	Deoxyadenosine dA
Guanine	Guanosine G	Deoxyguanosine dG
Thymine	5-Methyluridine m⁵U	Thymidine dT
Uracil	Uridine U	Deoxyuridine dU
Cytosine	Cytidine C	Deoxycytidine dC

Nucleosides are glycosylamines consisting of a nucleobase (often referred to as simply base) bound to a ribose or deoxyribose sugar via a beta-glycosidic linkage. Examples of nucleosides include cytidine, uridine, adenosine, guanosine, thymidine and inosine.

Biological function

Nucleosides can be phosphorylated by specific kinases in the cell on the sugar's primary alcohol group (-CH₂-OH), producing nucleotides, which are the molecular building-blocks of DNA and RNA.

Nucleosides can be produced by de novo synthesis pathways, in particular in the liver, but they are more abundantly supplied via ingestion and digestion of nucleic acids in the diet, whereby nucleotidases break down nucleotides (such as the thymidine monophosphate) into nucleosides (such as thymidine) and phosphate. The nucleosides, in turn, are subsequently broken down:

in the lumen of the digestive system by nucleosidases into nucleobases and ribose or deoxyribose.

In addition, nucleotides can be broken down:

inside the cell into nitrogenous bases, and ribose-1-phosphate or deoxyribose-1-phosphate.

Use in medicine and technology

In medicine several nucleoside analogues are used as antiviral or anticancer agents. The viral polymerase incorporates these compounds with non-canonical bases. These compounds are activated in the cells by being converted into nucleotides. They are administered as nucleosides since charged nucleotides cannot easily cross cell membranes.

In molecular biology, several analogues of the sugar backbone exist. Due to the low stability of RNA, which is prone to hydrolysis, several more stable alternative nucleoside/nucleotide analogues that correctly bind to RNA are used. This is achieved by using a different backbone sugar. These analogues include LNA, morpholino, PNA.

In sequencing, dideoxynucleotides are used. These nucleotides possess the non-canonical sugar dideoxyribose, which lacks 3' hydroxyl group (which accepts the phosphate). It therefore cannot bond with the next base and terminates the chain, as DNA polymerases cannot distinguish between it and a regular deoxyribonucleotide.

The structure elements of the nucleosides and the phosphate group bearing nucleotides

UpToDate Contents

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1. ヌクレオシド系逆転写酵素阻害剤の薬理学 pharmacology of nucleoside reverse transcriptase inhibitors
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English Journal

Preparation and chromatographic evaluation of zwitterionic stationary phases with controllable ratio of positively and negatively charged groups.

Cheng XD1, Hao YH1, Peng XT1, Yuan BF1, Shi ZG1, Feng YQ2.
Talanta.Talanta.2015 Aug 15;141:8-14. doi: 10.1016/j.talanta.2015.03.058. Epub 2015 Apr 2.
The present study described the preparation and application of zwitterionic stationary phases (ACS) with controllable ratio of positively charged tertiary amine groups and negatively charged carboxyl groups. Various parameters, including water content, pH values and ionic strength of the mobile phas
PMID 25966373

Preparation and characterization of host-guest system between inosine and β-cyclodextrin through inclusion mode.

Prabu S1, Sivakumar K2, Swaminathan M3, Rajamohan R4.
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.Spectrochim Acta A Mol Biomol Spectrosc.2015 Aug 5;147:151-7. doi: 10.1016/j.saa.2015.03.056. Epub 2015 Mar 9.
Inosine is a nucleoside that is formed when hypoxanthine is attached to a ribose ring (also known as a ribofuranose) via a β-N9-glycosidic bond. Inosine is commonly found in tRNAs. Inosine (INS) has been used widely as an antiviral drug. The inclusion complex of INS with β-CDx in solution phase is
PMID 25829161

The significant role of the intermolecular CH⋯O/N hydrogen bonds in governing the biologically important pairs of the DNA and RNA modified bases: a comprehensive theoretical investigation.

Brovarets' OO1, Yurenko YP, Hovorun DM.
Journal of biomolecular structure & dynamics.J Biomol Struct Dyn.2015 Aug;33(8):1624-52. doi: 10.1080/07391102.2014.968623. Epub 2014 Oct 28.
This paper is a logical continuation of the theoretical survey of the CH⋯O/N specific contacts in the nucleobase pairs using a wide arsenal of the modern methods, which was initiated in our previous study [J. Biomol. Struct. & Dynam., 2014, 32, 993-1022]. It was established that 34 CH⋯O and
PMID 25350312

Japanese Journal

Nudix hydrolaseファミリーによるビタミン補酵素型の代謝制御

吉村和也,伊藤大輔,丸田隆典,重岡成
ビタミン 87(1), 1-12, 2013-01-25
… Nudix hydrolases constitute a large family of proteins distributed in all living organisms and hydrolyze a wide variety of substrates, including coenzymes of niacin, pantothenic acid, and flavin, that contain a nucleoside diphosphate linked to some other moiety, X. …
NAID 110009578804

症例報告膜性腎症の治療経過中に発症したde novo B型肝炎の1例

大園芳範,蓮池悟,永田賢治
肝臓 54(1), 74-80, 2013-01-00
NAID 40019555787

Enzymatic and Molecular Characterization of Arabidopsis ppGpp Pyrophosphohydrolase, AtNUDX26

ITO Daisuke,KATO Takahiro,MARUTA Takanori [他]
Bioscience, Biotechnology, and Biochemistry 76(12), 2236-2241, 2012-12-00
NAID 40019531062

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★リンクテーブル★

リンク元	「nucleosidic」「ヌクレオシド」
拡張検索	「ribonucleoside diphosphate reductase」「dideoxynucleoside」「nonnucleoside reverse transcriptase inhibitors」「nucleoside diphosphate sugar」「methylated nucleoside」