2'-Amino-2'-deoxyguanosine
[CAS# 60966-26-9]

Identification

• Classification: Biochemical >> Nucleoside drugs >> Deoxynucleotides and their analogues
• Name: 2'-Amino-2'-deoxyguanosine
• Synonyms: 2-Amino-9-((2R,3R,4S,5R)-3-amino-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1,9-dihydro-6H-purin-6-one
• Molecular Formula: C₁₀H₁₄N₆O₄
• Molecular Weight: 282.26
• CAS Registry Number: 60966-26-9
• SMILES: C1=NC2=C(N1[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)N)N=C(NC2=O)N

Properties

• Density: 2.3±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.986, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P305+P351+P338

Discovery and Applications

2'-Amino-2'-deoxyguanosine is a modified nucleoside in which the amino group (-NH2) is attached to the 2'-position of the deoxyribose sugar, replacing the typical hydroxyl group (-OH) found in the natural nucleoside, deoxyguanosine. This structural modification has been investigated in the context of its biological activity and its potential applications in both molecular biology and medicinal chemistry.

The discovery of 2'-amino-2'-deoxyguanosine is rooted in the broader study of nucleoside analogs, which are chemical compounds that resemble the natural nucleosides but possess modifications to their structure. Nucleoside analogs have been of great interest for their potential use in the development of antiviral, anticancer, and other therapeutic agents. In particular, the modification of nucleosides at the 2'-position of the sugar ring can influence the compound's ability to interact with nucleic acids, enzymes, and cellular machinery, offering a pathway for the creation of novel drugs.

The primary application of 2'-amino-2'-deoxyguanosine lies in its use as a tool for studying DNA and RNA processes. Its modified structure allows it to participate in biochemical studies, particularly those related to the mechanism of action of DNA and RNA polymerases, which are enzymes involved in the synthesis of DNA and RNA. Researchers use such analogs to investigate how structural changes in nucleosides influence the fidelity of nucleic acid replication, repair, and transcription. The presence of an amino group at the 2'-position may also alter the interactions of this compound with nucleic acid structures, providing insight into the role of sugar modifications in the function of nucleic acids.

In addition to its utility in biochemical research, 2'-amino-2'-deoxyguanosine has been explored in the field of medicinal chemistry. As with many nucleoside analogs, its potential as an antiviral or anticancer agent has been investigated. Nucleoside analogs can act by mimicking the natural nucleotides involved in DNA or RNA synthesis, leading to the disruption of viral replication or the inhibition of cancer cell proliferation. Although 2'-amino-2'-deoxyguanosine has not been widely adopted as a therapeutic agent, its structure has been valuable in the development of other nucleoside-based drugs.

Another area where 2'-amino-2'-deoxyguanosine has found application is in the synthesis of modified nucleotides for use in the preparation of synthetic oligonucleotides. By incorporating such modified nucleosides into oligonucleotide sequences, researchers can study the effects of structural variations on nucleic acid hybridization, stability, and recognition by specific enzymes. These studies can inform the development of oligonucleotide-based therapeutics, such as antisense oligonucleotides, which are designed to bind to and modulate the activity of specific RNA targets.

In summary, 2'-amino-2'-deoxyguanosine is a nucleoside analog with important applications in molecular biology and medicinal chemistry. Its structural modification at the 2'-position of the sugar ring allows it to participate in studies of nucleic acid processes and serve as a building block for synthetic oligonucleotides. While it has not been widely adopted as a therapeutic agent, its role in the design and study of nucleoside analogs has contributed to the development of novel drugs and therapies.

References

1976. Identification of a novel aminonucleoside produced by Enterobacter sp. as 2'-amino-2'-deoxyguanosine. Chemical and Pharmaceutical Bulletin, 24(12).
DOI: 10.1248/cpb.24.2955

1992. 2′-Amino-2′-deoxyguanosine is a cofactor for self-splicing in group I catalytic RNA. Biochemical and Biophysical Research Communications, 183(2).
DOI: 10.1016/0006-291x(92)90560-8

2006. Improved synthesis of 2′-amino-2′-deoxyguanosine and its phosphoramidite. Bioorganic & Medicinal Chemistry, 14(3).
DOI: 10.1016/j.bmc.2005.08.050