2-Aminopurine riboside

2-Aminopurine riboside amidite

White powder, readily soluble in solvents such as dichloromethane, acetonitrile, and tetrahydrofuran, insoluble in water. Used for oligonucleic acid synthesis

Structural characteristics

Base part: 2-aminophosphate is used as the base, and its structure is similar to that of natural adenine and guanine. 2-aminopine can pair with thymine or cytosine in nucleic acids. This special pairing property makes it play an important role in studying the relationship between nucleic acid structure and function, etc.

The glycoside part: It is connected to the ribose through glycosidic bonds to form the nucleoside part.

Phosphoramidine group: Attached to the 3' position of the nucleoside, it is usually a (2-cyanoethyl)-(N, n-diisopropyl) phosphoramidine group. This group is the key part that exerts reactive activity in RNA synthesis and can undergo connection reactions with other nucleotide monomers or already synthesized RNA chains.

Protecting group: To ensure the selectivity and accuracy of the synthetic reaction, there is usually a protecting group at the 5' position of the nucleoside, such as dimethoxy-triphenylmethyl (DMT), etc., to protect the hydroxyl group and prevent unnecessary reactions during the synthesis process.

Function and application

It is mainly used for solid-phase synthesis of RNA. During the RNA synthesis process, it participates in the reaction as a monomer and connects with other nucleotide monomers through phosphoramidite groups, gradually forming RNA molecules with specific sequences. Due to the special properties of 2-aminopine, its introduction into RNA molecules can be used to study aspects such as RNA folding, RNA-ligand interaction, and RNA catalytic activity. For example, the structural changes of RNA under different external stimuli are studied by monitoring the fluorescence signal of 2-aminopine.

Synthesis method

Usually, 6-chloro-2-aminopurine nucleoside is used as the starting material. 2-Aminopurine nucleoside is obtained through reduction reaction, and then it undergoes appropriate protection and phosphatidylylation reaction. Eventually, 2-aminopurine riboside amidite is obtained. For instance, in the literature reports, there is a synthetic method that first hydrogenates and reduces 6-chloro-2-aminophosphine nucleoside with hydrogen and palladium-carbon to obtain 2-aminophosphine nucleoside, and then undergoes a series of protecting group modifications and phosphine amidation reactions to obtain the target product.

Properties and Stability

Appearance: Usually white to off-white powder.

Solubility: It is soluble in some organic solvents, such as dichloromethane and acetonitrile, but its solubility in water is relatively poor.

Stability: Sensitive to water and air, prone to hydrolysis and oxidation reactions. Therefore, during storage and use, it is necessary to keep it dry and in an inert atmosphere. Generally, it is recommended to store it at -20 ℃ or lower to extend its shelf life and maintain its reactivity.

Relevant parameters

Due to the fact that the specific structure may vary depending on the protecting group and the supplier, its molecular formula and molecular weight will also differ. If the common 5' -O - (dimethoxy-triphenylmethyl) -2-aminophosphine nucleoside -3 '- (2-cyanoethyl-N, n-diisopropyl) phosphine amide is taken as an example, its molecular formula may be around C41H51N7O7P, and the molecular weight is approximately 781.86. However, the actual parameters should refer to the manual of the specific product or relevant technical materials.