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Nucleoside - Revision history
2024-03-28T20:34:34Z
Revision history for this page on the wiki
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2012-08-20T14:24:50Z
<p>Robot: Automated text replacement (-{{SIB}} +, -{{EH}} +, -{{EJ}} +, -{{Editor Help}} +, -{{Editor Join}} +)</p>
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<td colspan="2" style="background-color: #fff; color: #202122; text-align: center;">Revision as of 14:24, 20 August 2012</td>
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WikiBot
https://www.wikidoc.org/index.php?title=Nucleoside&diff=549090&oldid=prev
Brian Blank at 18:01, 11 June 2009
2009-06-11T18:01:02Z
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<p><b>New page</b></p><div><!-- Here is a table of data; skip past it to edit the text. --><br />
{| border="1" cellpadding="2" cellspacing="0" align="right" style="margin-left:1em"<br />
|- align="center" valign="bottom"<br />
! Nitrogenous base<br />
! Nucleoside<br />
! Deoxynucleoside<br />
|- align="center" valign=""<br />
| br/>[[Adenine]]<br/><br />
| [[Image:A_chemical_structure.png|95px|Chemical structure of adenosine]]<br/>[[Adenosine]]<br/>A<br />
| <br/>[[Deoxyadenosine]]<br/>dA<br />
|- align="center" valign=""<br />
| <br/>[[Guanine]]<br/><br />
| [[Image:G_chemical_structure.png|123px|Chemical structure of guanosine]]<br/>[[Guanosine]]<br/>G <br />
| <br/>[[Deoxyguanosine]]<br/>dG<br />
|- align="center" valign=""<br />
| [[Image:Thymine_chemical_structure.png|63px|Chemical structure of thymine]]<br/>[[Thymine]]<br/><br />
| <br/>[[5-Methyluridine]]<br/>m<sup>5</sup>U <br />
| [[Image:dT_chemical_structure.png|87px|Chemical structure of thymidine]]<br/>Deoxythymidine<br/>dT<br />
|- align="center" valign=""<br />
| [[Image:Uracil_chemical_structure.png|51px|Chemical structure of uracil]]<br/>[[Uracil]]<br/><br />
| <br/>[[Uridine]]<br/>U<br />
| <br/>[[Deoxyuridine]]<br/>dU<br />
|- align="center" valign=""<br />
| [[Image:Cytosine_chemical_structure.png|51px|Chemical structure of cytosine]]<br/>[[Cytosine]]<br/><br />
| <br/>[[Cytidine]]<br/>C<br />
| <br/>[[Deoxycytidine]]<br/>dC<br />
|-<br />
|}<br />
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==Overview==<br />
'''Nucleosides''' are [[glycosylamine]]s made by attaching a [[nucleobase]] (often referred to simply as base) to a [[ribose]] or [[deoxyribose]] ring. Examples of these include [[cytidine]], [[uridine]], [[adenosine]], [[guanosine]], [[thymidine]] and [[inosine]]. In short, a nucleoside is a base linked to sugar.<br />
<br />
Nucleosides can be [[phosphorylation|phosphorylated]] by specific [[kinase]]s in the cell, producing [[nucleotide]]s, which are the molecular building blocks of [[DNA]] and [[RNA]].<br />
<br />
Nucleosides are produced as the second step in nucleic acid digestion, whereby [[nucleotidase]]s break down ''[[nucleotide]]s'' (such as the [[thymine]] nucleotide) into ''nucleosides'' (such as [[thymidine]]) and phosphate. The nucleosides, in turn, are subsequently broken down<br />
* in the [[lumen]] of the digestive system by nucleosidases into nitrogenous bases and [[ribose]] (or [[deoxyribose]]), and<br />
* inside the cell by [[nucleoside phosphorylase]]s into [[nitrogenous base]]s, and ribose-1-phosphate (or deoxyribose-1-phosphate).<br />
Nucleosides can be produced by combining nucleobases with deoxyribose rings as well.<br />
<br />
Nucleosides differ from nucleotides by having a [[hydroxyl]] group attached to carbon number 5 (the one that isn't in the ring) of the ribose, rather than one or more phosphate groups.<br />
<br />
In medicine several [[nucleoside analogues]] are used as antiviral or anticancer agents. The viral polymerase incorporates these compounds with non-canon bases. These compounds are activated in the cells by being converted into nucleotides, they are administered as nuclosides since charged nucleotides cannot easily cross cell membranes.<br />
<br />
In molecular biology several [[Nucleic acid analogues|analogues]] of the sugar back bone exist. Due to the low stability of RNA, which is prone to hydrolysis, several more stable alternative nucleoside/nucleotide analogues are used which correctly bind to RNA. This is achieved by using a different backbone sugar. These analogues includ LNA, [[morpholino]], PNA.<br />
<br />
In sequencing [[dideoxynucleotides]] are used. These nucleotides posses a non-canon sugar, dideoxyribose which lacks 3' hydroxyl group (which accepts the phosphate) and therefore cannot bond with the next base, terminating the chain as DNA polymerases mistake it for a regular deoxyribonucleotide.<br />
<br />
<br style="clear: both;" /><br />
<br />
== See also ==<br />
* [[Nucleobase]]<br />
* [[Nucleotide]]<br />
* [[RNA]]<br />
* [[Adenosine triphosphate]] (ATP)<br />
* [[Nucleic acid analogues]]<br />
<br />
<br />
{{Nucleic acids}}<br />
{{SIB}}<br />
[[Category:Nucleosides|*]]<br />
<br />
[[ca:Nucleòsid]]<br />
[[cs:Nukleosid]]<br />
[[da:Nukleosid]]<br />
[[de:Nukleoside]]<br />
[[el:Νουκλεοζίτης]]<br />
[[es:Nucleósido]]<br />
[[fr:Nucléoside]]<br />
[[gl:Nucleósido]]<br />
[[id:Nukleosida]]<br />
[[it:Nucleoside]]<br />
[[ka:ნუკლეოზიდი]]<br />
[[lt:Nukleozidas]]<br />
[[hu:Nukleozid]]<br />
[[nl:Nucleoside]]<br />
[[ja:ヌクレオシド]]<br />
[[pl:Nukleozydy]]<br />
[[fi:Nukleosidi]]<br />
[[sv:Nukleosid]]<br />
[[zh:核苷]]<br />
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{{WH}}<br />
<br />
{{WS}}</div>
Brian Blank