2deoxyinosine

2-deoxyinosine, also known as deoxyinosine or hypoxanthine deoxyriboside, is a nucleoside that is a derivative of deoxyguanosine and deoxyadenosine. It is composed of a hypoxanthine molecule attached to a deoxyribose sugar molecule via a beta-N9-glycosidic bond. 2-deoxyinosine is an analog of deoxyadenosine and deoxyguanosine, differing in the base. Instead of adenine or guanine, it contains hypoxanthine, which is a purine base.

This compound can arise from the deamination of deoxyadenosine, a process where an amino group is replaced by a carbonyl group. This can occur both spontaneously in DNA and through enzymatic action. The presence of 2-deoxyinosine within DNA can lead to mispairing during DNA replication. Specifically, hypoxanthine has hydrogen bonding properties that are similar to guanine and adenine, but it preferentially pairs with cytosine, mimicking adenine-guanine pairing. This can lead to point mutations in subsequent rounds of replication.

In research, 2-deoxyinosine is used as a tool in molecular biology and genetics to study DNA repair mechanisms and mutation processes. It can also be incorporated into synthetic oligonucleotides to probe DNA structure and function. While not a standard DNA base, its potential to arise and its impact on genetic integrity make it a compound of interest in understanding DNA stability and mutagenesis.