Nucleoside

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Nitrogenous base Nucleoside Deoxynucleoside
Chemical structure of adenine
Adenine
Chemical structure of adenosine
Adenosine
A
Chemical structure of deoxyadenosine
Deoxyadenosine
dA
Chemical structure of guanine
Guanine
Chemical structure of guanosine
Guanosine
G
Chemical structure of deoxyguanosine
Deoxyguanosine
dG
Chemical structure of thymine
Thymine
Chemical structure of 5-methyluridine
5-Methyluridine
m5U
Chemical structure of thymidine
Deoxythymidine
dT
Chemical structure of uracil
Uracil
Chemical structure of uridine
Uridine
U
Chemical structure of deoxyuridine
Deoxyuridine
dU
Chemical structure of cytosine
Cytosine
Chemical structure of cytidine
Cytidine
C
Chemical structure of deoxycytidine
Deoxycytidine
dC

Nucleosides are glycosylamines consisting of a nucleobase (often referred to simply base) bound to a ribose or deoxyribose sugar. Examples of these include cytidine, uridine, adenosine, guanosine, thymidine and inosine.

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 are produced as the second step in nucleic acid digestion, whereby nucleotidases break down nucleotides (such as the thymine nucleotide) into nucleosides (such as thymidine) and phosphate. The nucleosides, in turn, are subsequently broken down:

Nucleosides can be produced by combining nucleobases with deoxyribose rings as well.

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.

In molecular biology several 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 include LNA, morpholino, PNA.

In sequencing dideoxynucleotides are used. These nucleotides possess 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.

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


See also


Wikipedia content modification information:

  • This page was last modified on 23 August 2008, at 15:19.

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