Nucleobase

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Base pairing: Two base pairs are produced by four nucleotide monomers, nucleobases are in blue. Guanine (G) is paired with cytosine (C) via three hydrogen bonds, in red. Adenine (A) is paired with uracil (U) via two hydrogen bonds, in red.
Purine nucleobases are fused-ring molecules.
Pyrimidine nucleobases are simple ring molecules.

Nucleobases (nitrogenous bases or simply bases) are

deoxyribonucleic acid (DNA). Five nucleobases—adenine (A), cytosine (C), guanine (G), thymine (T), and uracil (U)—are called primary or canonical. They function as the fundamental units of the genetic code, with the bases A, G, C, and T being found in DNA while A, G, C, and U are found in RNA. Thymine and uracil are distinguished by merely the presence or absence of a methyl group on the fifth carbon (C5) of these heterocyclic six-membered rings.[1][page needed
] In addition, some viruses have
aminoadenine (Z) instead of adenine. It differs in having an extra amine group, creating a more stable bond to thymine.[2]

Adenine and guanine have a

amino group (−NH2), at the C6 carbon in adenine and C2 in guanine.[3] Similarly, the simple-ring structure of cytosine, uracil, and thymine is derived of pyrimidine
, so those three bases are called the pyrimidine bases.

Each of the base pairs in a typical double-

carbonyl
groups on the complementary bases.

Nucleobases such as adenine, guanine,

2,6-diaminopurine, and 6,8-diaminopurine may have formed in outer space as well as on earth.[4][5][6]

The origin of the term base reflects these compounds' chemical properties in acid–base reactions, but those properties are not especially important for understanding most of the biological functions of nucleobases.

Structure

Chemical structure of DNA, showing four nucleobase pairs produced by eight nucleotides: adenine (A) is joined to thymine (T), and guanine (G) is joined to cytosine (C). + This structure also shows the directionality of each of the two phosphate-deoxyribose backbones, or strands. The 5' to 3' (read "5 prime to 3 prime") directions are: down the strand on the left, and up the strand on the right. The strands twist around each other to form a double helix structure.

At the sides of nucleic acid structure, phosphate molecules successively connect the two sugar-rings of two adjacent nucleotide monomers, thereby creating a long chain

transcription
of the encoded information found in DNA.

Modified nucleobases

DNA and RNA also contain other (non-primary) bases that have been modified after the nucleic acid chain has been formed. In DNA, the most common modified base is

7-methylguanosine (m7G).[7][8]

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,[9] and uracil results from deamination of cytosine.

Modified purine nucleobases

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 nucleobases

These are examples of modified cytidine, thymidine or uridine.

Nucleobase
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
Pseudouridine

Artificial nucleobases

Main article: Nucleic acid analogue

A vast number of nucleobase analogues exist. The most common applications are used as fluorescent probes, either directly or indirectly, such as

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.[10][11]

In medicine, several nucleoside analogues are used as anticancer and antiviral agents. 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 as charged nucleotides cannot easily cross cell membranes.[citation needed] At least one set of new base pairs has been announced as of May 2014.[12]

Prebiotic condensation of nucleobases with ribose

In order to understand how life arose knowledge is required of chemical pathways that permit formation of the key building blocks of life under plausible prebiotic conditions. According to the RNA world hypothesis free-floating ribonucleotides were present in the primordial soup. These were the fundamental molecules that combined in series to form RNA. 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 evolution. Nam et al.[13] demonstrated the direct condensation of nucleobases with ribose to give ribonucleosides in aqueous microdroplets, a key step leading to RNA formation. Similar results were obtained by Becker et al.[14]

See also

  • Nucleoside – Any of several glycosylamines comprising a nucleobase and a sugar molecule
  • Nucleotide – Biological molecules constituting nucleic acids
  • Nucleic acid notation – Universal notation using the Roman characters A, C, G, and T to call the four DNA nucleotides
  • Nucleic acid sequence – Succession of nucleotides in a nucleic acid

References

  1. ISBN 9780470015902
    .
  2. ^ "Some viruses thwart bacterial defenses with a unique genetic alphabet". 5 May 2021.
  3. ^ Berg JM, Tymoczko JL, Stryer L. "Section 25.2, Purine Bases Can Be Synthesized de Novo or Recycled by Salvage Pathways". Biochemistry. 5th Edition. Retrieved 11 December 2019.
  4. PMID 21836052
    .
  5. ^ Steigerwald, John (8 August 2011). "NASA Researchers: DNA Building Blocks Can Be Made in Space". NASA. Retrieved 10 August 2011.
  6. ^ ScienceDaily Staff (9 August 2011). "DNA Building Blocks Can Be Made in Space, NASA Evidence Suggests". ScienceDaily. Retrieved 9 August 2011.
  7. ^ Stavely, Brian E. "BIOL2060: Translation". www.mun.ca. Retrieved 17 August 2020.
  8. ^ "Role of 5' mRNA and 5' U snRNA cap structures in regulation of gene expression" – Research – Retrieved 13 December 2010.
  9. PMID 1557408
    .
  10. PMID 15051811
    .
  11. PMID 17693436
    .
  12. PMID 24805238
    .
  13. PMID 29255025
    .
  14. S2CID 203719976
    .

External links
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