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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).
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. In similar manner, deamination of cytosine results in uracil.
- 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.
These are incorporated into the growing chain during RNA and/or DNA synthesis.
|Nucleobase||Chemical structure of adenine
|Nucleoside||Chemical structure of adenosine
Modified purine bases
These are examples of modified adenosine or guanosine.
|Nucleobase||Chemical structure of hypoxanthine
|Chemical structure of xanthine
|Chemical structure of 7-methylguanine|
|Nucleoside||Chemical structure of inosine
|Chemical structure of xanthosine
|Chemical structure of 7-methylguanosine|
Modified pyrimidine bases
These are examples of modified cytidine, thymidine or uridine.
|Nucleobase||Chemical structure of dihydrouracil
|Chemical structure of 5-methylcytosine
|Chemical structure of 5-hydroxymethylcytosine|
|Nucleoside||Chemical structure of dihydrouridine
|Chemical structure of 5-methylcytidine
- 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.
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.
|Nucleic acids edit|
|Nucleobases: Adenine - Thymine - Uracil - Guanine - Cytosine - Purine - Pyrimidine|
|Nucleosides: Adenosine - Uridine - Guanosine - Cytidine - Deoxyadenosine - Thymidine - Deoxyguanosine - Deoxycytidine|
|Nucleotides: AMP - UMP - GMP - CMP - ADP - UDP - GDP - CDP - ATP - UTP - GTP - CTP - cAMP - cGMP|
|Deoxynucleotides: dAMP - dTMP - dUMP - dGMP - dCMP - dADP - dTDP - dUDP - dGDP - dCDP - dATP - dTTP - dUTP - dGTP - dCTP|
|Nucleic acids: DNA - RNA - LNA - PNA - mRNA - ncRNA - miRNA - rRNA - siRNA - tRNA - cDNA - snRNA - snoRNA - mtDNA - Oligonucleotide
|This page uses Creative Commons Licensed content from Wikipedia (view authors).|
- BIOL2060: Translation
- "Role of 5' mRNA and 5' U snRNA cap structures in regulation of gene expression" - Research - Retrieved 13 December 2010.
- T Nguyen, D Brunson, C L Crespi, B W Penman, J S Wishnok, and S R Tannenbaum, DNA damage and mutation in human cells exposed to nitric oxide in vitro, Proc Natl Acad Sci U S A. 1992 April 1; 89(7): 3030–3034