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Method for preparing 7-methyl guanosine
**Chinese Name:** 7-Methylguanosine
**English Name:** 7-Methylguanosine
**Molecular Formula:** Câ‚â‚Hâ‚â‚…Nâ‚…Oâ‚…
**Molecular Weight:** 297.27 g/mol
**Physicochemical Properties:**
This compound undergoes hydrolysis when heated at 100°C for one hour in water, methanol, or 1 mol/L sulfuric acid, yielding 7-methylguanine and D-ribose. Under neutral or alkaline conditions, the molecule undergoes ring-opening to form 5-N-methylformamide-6-ribosylaminoisocytosine (I). Further acid treatment converts this intermediate into 6-amino-5-N-methylformamide isocytosine (II) along with D-ribose.
**Physical and Chemical Parameters:**
The melting point of the monohydrate form is 165°C. The pKa value of the acidic group is approximately 7.1.
**Storage Conditions:**
It should be stored below 0°C to maintain stability and prevent degradation.
**Preparation Methods:**
**Method 1:**
Start with 10 g of guanosine that contains two molecules of water of crystallization. Dissolve it in 100 mL of N,N-dimethylacetamide containing 10 g of methyl iodide. Stir the mixture at 30°C for 30 hours. Afterward, filter the solution using a filter aid. Add 500 mL of ethanol to the filtrate, then dilute the solution to 1200 mL using petroleum ether (with a melting point range of 65–110°C) to obtain an oily residue. Treat this residue with 300 mL of acetone to induce precipitation, resulting in a white solid. Stir the suspension for 5 minutes, filter, and wash the solid with acetone. Then, use diethyl ether for further washing and drying to yield 8 g of the iodide salt of 7-methylguanosine.
Dissolve the product in 70 mL of water, cool the solution to 10°C, and add concentrated ammonia to adjust the pH to 9.5. Next, add 700 mL of acetone and adjust the pH to 9 using more ammonia. Filter the mixture, wash the precipitate with acetone and ether, and dry it to obtain pure 7-methylguanosine with a melting point of 160–161°C.
**Method 2:**
Take 20 g of guanosine containing two molecules of water of crystallization and dissolve it in 200 mL of N,N-dimethylacetamide containing 15 g of dimethyl sulfate. Stir the mixture at 25–28°C for 6 hours. Filter the solution through a filter aid and cool the clear filtrate to 15–20°C. Adjust the pH to 8 using ammonia water. Add 600 mL of acetone and allow the mixture to stand at 15–20°C for 2 hours. Filter the precipitate, wash it with absolute ethanol, then treat it with ether while stirring. Filter, wash again with ether, and dry to obtain 7-methylguanosine with a melting point of 159–160°C.
This compound is widely used in nucleotide chemistry, particularly in the synthesis of modified RNA molecules and as a precursor in various biochemical studies. Its stability under certain conditions makes it a valuable reagent in both research and pharmaceutical applications.
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