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File:AGCT RNA mini.png

Nucleobases are nitrogen-containing biological compounds (nitrogenous bases) found within deoxyribonucleic acid (DNA), ribonucleic acid (RNA), nucleotides, and nucleosides. Often simply called bases in genetics, their ability to form base-pairs and to stack upon one another lead directly to the helical structure of DNA and RNA.

Use of the word base is historical, in reference to the chemical properties of nucleobases in acid-base reactions within the test tube, and is not especially relevant or important for understanding most of their biological functions.

The primary nucleobases are cytosine (DNA and RNA), guanine (DNA and RNA), adenine (DNA and RNA), thymine (DNA) and uracil (RNA), abbreviated as C, G, A, T, and U, respectively. Because A, G, C, and T appear in the DNA, these molecules are called DNA-bases; A, G, C, and U are called RNA-bases. Uracil replaces thymine in RNA. These two bases are identical except that uracil lacks the 5' methyl group. Adenine and guanine belong to the double-ringed class of molecules called purines (abbreviated as R). Cytosine, thymine, and uracil are all pyrimidines (abbreviated as Y).

In normal spiral DNA the bases form pairs between the two strands: A with T and C with G. Purines pair with pyrimidines mainly for dimensional reasons - only this combination fits the constant width geometry of the DNA spiral. The A-T and C-G pairings are required to match the hydrogen bonds between the amine and carbonyl groups on the complementary bases.

The compound formed when a nucleobase forms a glycosidic bond with the 1' anomeric carbon of a ribose or deoxyribose is called a nucleoside, and a nucleoside with one or more phosphate groups attached at the 5' carbon is called a nucleotide.

Apart from adenine (A), cytosine (C), guanine (G), thymine (T) and uracil (U), DNA and RNA also contain bases that have been modified after the nucleic acid chain has been formed. In DNA, the most common modified base is 5-methylcytosine (m5C). In RNA, there are many modified bases, including those contained in the nucleosides pseudouridine (Ψ), dihydrouridine (D), inosine (I), and 7-methylguanosine (m7G).[1][2]

Hypoxanthine and xanthine are two of the many bases created through mutagen presence, both of them through deamination (replacement of the amine-group with a carbonyl-group). Hypoxanthine is produced from adenine, xanthine from guanine.[3] In similar manner, deamination of cytosine results in uracil.


StructureEdit

  • The "skeleton" of adenine and guanine is purine, hence the name purine-bases.
  • The "skeleton" of cytosine, uracil, and thymine is pyrimidine, hence pyrimidine-bases.

Primary basesEdit

These are incorporated into the growing chain during RNA and/or DNA synthesis.

Nucleobase Chemical structure of adenine
Adenine
Guanine chemical structure
Guanine
Thymine chemical structure
Thymine
Cytosine chemical structure
Cytosine
Uracil chemical structure
Uracil
Nucleoside Chemical structure of adenosine
Adenosine
A
G chemical structure
Guanosine
G
T chemical structure
Thymidine
T
C chemical structure
Cytidine
C
U chemical structure
Uridine
U

Modified purine basesEdit

These are examples of modified adenosine or guanosine.

Nucleobase Chemical structure of hypoxanthine
Hypoxanthine
Chemical structure of xanthine
Xanthine
Chemical structure of 7-methylguanine
7-Methylguanine
Nucleoside Chemical structure of inosine
Inosine
I
Chemical structure of xanthosine
Xanthosine
X
Chemical structure of 7-methylguanosine
7-Methylguanosine
m7G

Modified pyrimidine basesEdit

These are examples of modified cytidine, thymidine or uridine.

Nucleobase Chemical structure of dihydrouracil
5,6-Dihydrouracil
Chemical structure of 5-methylcytosine
5-Methylcytosine
Chemical structure of 5-hydroxymethylcytosine
5-Hydroxymethylcytosine
Nucleoside Chemical structure of dihydrouridine
Dihydrouridine
D
Chemical structure of 5-methylcytidine
5-Methylcytidine
m5C

Novel basesEdit

Main article: Nucleic acid analogues

A vast number of nucleobase analogues exist. The most common applications are used as fluorescent probes, either directly or indirectly, such as aminoallyl nucleotide, which are used to label cRNA or cDNA in microarrays. Several groups are working on alternative "extra" base pairs to extend the genetic code, such as isoguanine and isocytosine or the fluorescent 2-amino-6-(2-thienyl)purine and pyrrole-2-carbaldehyde.[citation needed]

In medicine, several nucleoside analogues are used as anticancer and antiviral 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 nucleosides as charged nucleotides cannot easily cross cell membranes.[citation needed]

See also Edit

External linksEdit

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