80791-88-4

Basic information

• Product Name: 3'-OMe-2-NH2-A
• Synonyms: 3'-OMe-2-NH2-A;3'-O-Methyl-2-AMino-adenosine;Adenosine, 2-aMino-3'-O-Methyl-;3'-O-Methyl-2,6-diaminopurine riboside;2-Amino-3'-O-methyladenosine
• CAS NO: 80791-88-4
• Molecular Formula: C11H16N6O4
• Molecular Weight: 296.28254
• Mol File: 80791-88-4.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3'-OMe-2-NH2-A(CAS DataBase Reference)
• NIST Chemistry Reference: 3'-OMe-2-NH2-A(80791-88-4)
• EPA Substance Registry System: 3'-OMe-2-NH2-A(80791-88-4)

Safety Data

• Hazardous Substances Data: 80791-88-4(Hazardous Substances Data)

Usage

General Description

"3'-OMe-2-NH2-A" is a chemical compound that consists of a modified adenosine molecule with a 3'-methoxy and a 2-amino group. It is commonly used in nucleic acid research as a building block for the synthesis of modified RNA molecules. 3'-OMe-2-NH2-A is often utilized in the development of novel therapeutic strategies and drug delivery systems due to its ability to modulate the properties of nucleic acids. Its unique structure and properties make "3'-OMe-2-NH2-A" a valuable tool in the study of nucleic acid chemistry and its applications in biotechnology and medicine.

Upstream product

• 186581-53-3 diazomethane 
• 2096-10-8 adenosine-2-amine 
• 118-00-3 G 

Relevant articles and documents

An efficient process for synthesis of 2′-O-methyl and 3′-O-methyl guanosine from 2-aminoadenosine using diazomethane and the catalyst stannous chloride

An improved strategy for the selective synthesis of 2′- O -methyl and 3′- O -methyl guanosine from 2-aminoadenosine is reported by using the catalyst stannous chloride. The regioselectivity of the 2′ and 3′- O -alkylation was achieved by optimizing the addition, timing, and concentration of the catalysts and diazomethane during the methylation reaction. An efficient and selective alkylation at 2′-OH of 2-aminoadenosine was achieved by mixing a stoichiometric amount of stannous chloride at room temperature in DMF. The reaction mixture was stirred at 50°C for 1 min and immediately followed by addition of diazomethane. The resulting 2′- O -methyl 2-aminoadenosine was treated with the enzyme adenosine deaminase, which resulted in an efficient conversion to the desired 2′- O -methylguanosine (98% yield). The product was isolated by crystallization. In contrast, the methylation at 3′-OH of 2-aminoadenosine was achieved by mixing a stoichiometric amount of stannous chloride in DMF and stirring at 50°C for 15 min, followed by addition of diazomethane. The resulting mixture containing 3′- O -methyl-2- aminoadenosine in 90% yield and 2′- O -methyl-2-aminoadenosine in 10% yield was treated with the enzyme adenosine deaminase, which preferentially deaminated only 3′- O -methyl-2-aminoadenosine, resulting in the production of 3′- O -methylguanosine in 88% yield. Due to the extremely low solubility 3′- O -methylguanosine, the compound precipitated and was isolated by centrifugation. This synthetic route obviates the chromatographic purification. Selective monomethylation is achieved by using the unprotected ribonucleoside. As a result, the method described herein represents a significant improvement over the current synthetic approach by providing superior product yield and economy, a much more facile purification of 2′,3′- O -methylated isomers, and eliminating the need for protected ribonucleosides reagents. Copyright Taylor & Francis Group, LLC.