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A base analog is a chemical that can substitute for a normal nucleobase
Nucleobase

Nucleobases are the parts of DNA and RNA that may be involved in pairing . The main ones are cytosine, guanine, adenine , thymine and uracil , abbreviated as C, G, A, T, and U, respectively....
 in nucleic acid
Nucleic acid

A nucleic acid is a macromolecule composed of chains of monomeric nucleotides. In biochemistry these molecules carry genetic information or form structures within Cell ....
s.

A common example would be 5-bromouracil
5-Bromouracil

5-Bromouracil is a brominated derivative of uracil that acts as an antimetabolite or base analog, substituting for thymine in DNA and can induce DNA mutation in the same way as 2-aminopurine....
 (5BU), the abnormal base found in the mutagenic nucleotide analog BrdU. When a nucleotide containing 5-bromouracil is incorporated into the DNA, it is most likely to pair with adenine; however, it can spontaneously shift into another isomer
Isomer

In chemistry, isomers are compounds with the same molecular formula but different structural formulae. Isomers do not necessarily share similar properties unless they also have the same functional groups....
 which pairs with a different nucleobase
Nucleobase

Nucleobases are the parts of DNA and RNA that may be involved in pairing . The main ones are cytosine, guanine, adenine , thymine and uracil , abbreviated as C, G, A, T, and U, respectively....
, guanine
Guanine

Guanine is one of the five main nucleobases found in the nucleic acids DNA and RNA, the others being adenine, cytosine, thymine, and uracil. In DNA, guanine is paired with cytosine....
. If this happens during DNA replication, a guanine will be inserted opposite the base analog, and in the next DNA replication, that guanine will pair with a cytosine.






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A base analog is a chemical that can substitute for a normal nucleobase
Nucleobase

Nucleobases are the parts of DNA and RNA that may be involved in pairing . The main ones are cytosine, guanine, adenine , thymine and uracil , abbreviated as C, G, A, T, and U, respectively....
 in nucleic acid
Nucleic acid

A nucleic acid is a macromolecule composed of chains of monomeric nucleotides. In biochemistry these molecules carry genetic information or form structures within Cell ....
s.

A common example would be 5-bromouracil
5-Bromouracil

5-Bromouracil is a brominated derivative of uracil that acts as an antimetabolite or base analog, substituting for thymine in DNA and can induce DNA mutation in the same way as 2-aminopurine....
 (5BU), the abnormal base found in the mutagenic nucleotide analog BrdU. When a nucleotide containing 5-bromouracil is incorporated into the DNA, it is most likely to pair with adenine; however, it can spontaneously shift into another isomer
Isomer

In chemistry, isomers are compounds with the same molecular formula but different structural formulae. Isomers do not necessarily share similar properties unless they also have the same functional groups....
 which pairs with a different nucleobase
Nucleobase

Nucleobases are the parts of DNA and RNA that may be involved in pairing . The main ones are cytosine, guanine, adenine , thymine and uracil , abbreviated as C, G, A, T, and U, respectively....
, guanine
Guanine

Guanine is one of the five main nucleobases found in the nucleic acids DNA and RNA, the others being adenine, cytosine, thymine, and uracil. In DNA, guanine is paired with cytosine....
. If this happens during DNA replication, a guanine will be inserted opposite the base analog, and in the next DNA replication, that guanine will pair with a cytosine. This results in a change in one base pair of DNA, specifically a transition
Transition (genetics)

In genetics, a transition is a mutation changing a purine to another purine nucleotide or a pyrimidine to another pyrimidine nucleotide . Approximately two out of every three single nucleotide polymorphisms are transitions....
 mutation
Mutation

In biology, mutations are changes to the nucleotide sequence of the genetic material of an organism. Mutations can be caused by copying errors in the genetic material during cell division, by exposure to ultraviolet or ionizing radiation, chemical mutagens, or virus , or can be induced by the organism, itself, by cellular processes such as s...
.

5bu 2

See also

  • Antimetabolite
    Antimetabolite

    An antimetabolite is a chemical that enzyme inhibition the use of a metabolite, which is another chemical that is part of normal metabolism. Such substances are often similar in structure to the metabolite that they interfere with, such as the antifolates that interfere with the use of folic acid....