Nucleoside

Nucleosides are glycosylamines that can be thought of as nucleotides without a phosphate group.
A nucleoside consists simply of a nucleobase (also termed a nitrogenous base) and a five-carbon
sugar (ribose or 2'-deoxyribose) whereas a nucleotide is composed of a nucleobase, a five-carbon
sugar, and one or more phosphate groups. In a nucleoside, the anomeric carbon is linked through a
glycosidic bond to the N9 of a purine or the N1 of a pyrimidine. Nucleotides are the molecular
building blocks of DNA and RNA.

deoxyadenosine adenosine

Two corresponding nucleosides, the deoxyribonucleoside,

deoxyadenosine, and the ribonucleoside, adenosine. The line-angle
molecular representation implies carbon atoms at each angle, each
with enough hydrogen atoms to fill its four-bond valency.

List of nucleosides and corresponding nucleobases

This list does not include modified nucleobases and the corresponding nucleosides

Each chemical has a short symbol, useful when the chemical family is clear from the context, and a
longer symbol, if further disambiguation is needed. For example, long nucleobase sequences in
genomes are usually described by CATG symbols, not Cyt-Ade-Thy-Gua (see Nucleic acid sequence
§ Notation).
 Nitrogenous base Ribonucleoside Deoxyribonucleoside

adenine
adenosine deoxyadenosine
symbol A or Ade
symbol A or Ado symbol dA or dAdo

guanine
guanosine deoxyguanosine
symbol G or Gua
symbol G or Guo symbol dG or dGuo

thymine thymidine
5-methyluridine
(5-methyluracil) (deoxythymidine)
(ribothymidine)
symbol T or Thy symbol dT or dThd
symbol m⁵U
(dated: T or Thd)

uracil
uridine deoxyuridine
symbol U or Ura
symbol U or Urd symbol dU or dUrd

cytosine
cytidine deoxycytidine
symbol C or Cyt
symbol C or Cyd symbol dC or dCyd

Sources

Nucleosides can be produced from nucleotides de novo, particularly 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.[1][2][3][4] 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 locked nucleic acids (LNA), morpholinos and peptide nucleic acids (PNA).

In sequencing, dideoxynucleotides are used. These nucleotides possess the non-canonical sugar
dideoxyribose, which lacks 3' hydroxyl group (which accepts the phosphate). DNA polymerases
cannot distinguish between these and regular deoxyribonucleotides, but when incorporated a
dideoxynucleotide cannot bond with the next base and the chain is terminated.

Prebiotic synthesis of ribonucleosides

In order to understand how life arose, knowledge is required of the chemical pathways that permit
formation of the key building blocks of life under plausible prebiotic conditions. According to the
RNA world hypothesis free-floating ribonucleosides and ribonucleotides were present in the
primitive soup. Molecules as complex as RNA must have arisen from small molecules whose
reactivity was governed by physico-chemical processes. RNA is composed of purine and pyrimidine
nucleotides, both of which are necessary for reliable information transfer, and thus Darwinian
natural selection and evolution. Nam et al.[5] demonstrated the direct condensation of nucleobases
with ribose to give ribonucleosides in aqueous microdroplets, a key step leading to RNA formation.
Also, a plausible prebiotic process for synthesizing pyrimidine and purine ribonucleosides and
ribonucleotides using wet-dry cycles was presented by Becker et al.[6]
See also

Arabinosyl nucleosides

Nucleobase

Salvage enzyme

Synthesis of nucleosides

References

1. Ramesh, Deepthi; Vijayakumar, Balaji Gowrivel; Kannan, Tharanikkarasu (December 2020).

"Therapeutic potential of uracil and its derivatives in countering pathogenic and physiological
disorders". European Journal of Medicinal Chemistry. 207 112801.
doi:10.1016/[Link].2020.112801 ([Link] .
PMID 32927231 ([Link] . S2CID 221724578 ([Link]
[Link]/CorpusID:221724578) .

2. Galmarini, Carlos M.; MacKey, John R.; Dumontet, Charles (2002). "Nucleoside analogues and
nucleobases in cancer treatment". The Lancet Oncology. 3 (7): 415–424. doi:10.1016/S1470-
2045(02)00788-X ([Link] .
PMID 12142171 ([Link] .

3. Jordheim, Lars Petter; Durantel, David; Zoulim, Fabien; Dumontet, Charles (2013). "Advances in
the development of nucleoside and nucleotide analogues for cancer and viral diseases".
Nature Reviews Drug Discovery. 12 (6): 447–464. doi:10.1038/nrd4010 ([Link]
8%2Fnrd4010) . PMID 23722347 ([Link] .
S2CID 39842610 ([Link] .

4. Ramesh, Deepthi; Vijayakumar, Balaji Gowrivel; Kannan, Tharanikkarasu (12 February 2021).
"Advances in Nucleoside and Nucleotide Analogues in Tackling Human Immunodeficiency
Virus and Hepatitis Virus Infections" ([Link]
[Link]/doi/epdf/10.1002/cmdc.202000849) .
ChemMedChem. 16 (9): 1403–1419. doi:10.1002/cmdc.202000849 ([Link]
2Fcmdc.202000849) . PMID 33427377 ([Link] .
S2CID 231576801 ([Link] . Archived from the
original ([Link]
9) on 14 December 2021. Retrieved 13 March 2021.
 5. Nam, Inho; Nam, Hong Gil; Zare, Richard N. (2018-01-02). "Abiotic synthesis of purine and
pyrimidine ribonucleosides in aqueous microdroplets" ([Link]
cles/PMC5776833) . Proceedings of the National Academy of Sciences of the United States
of America. 115 (1): 36–40. Bibcode:2018PNAS..115...36N ([Link]
s/2018PNAS..115...36N) . doi:10.1073/pnas.1718559115 ([Link]
718559115) . PMC 5776833 ([Link] .
PMID 29255025 ([Link] .

6. Becker, Sidney; Feldmann, Jonas; Wiedemann, Stefan; Okamura, Hidenori; Schneider, Christina;
Iwan, Katharina; Crisp, Antony; Rossa, Martin; Amatov, Tynchtyk; Carell, Thomas (2019-10-04).
"Unified prebiotically plausible synthesis of pyrimidine and purine RNA ribonucleotides" (http
s://[Link]/71503/1/Science_Becker_2019.pdf) (PDF). Science. 366
(6461): 76–82. Bibcode:2019Sci...366...76B ([Link]
6...76B) . doi:10.1126/science.aax2747 ([Link] .
PMID 31604305 ([Link] . S2CID 203719976 ([Link]
[Link]/CorpusID:203719976) . Archived ([Link]
21009/[Link] (PDF) from the
original on 2022-10-09.

External links

Media related to Nucleosides at Wikimedia Commons