Water → 2-Thioadenosine

Participants

Reaction Steps

16g of adenosine 1-oxide monohydrate (53.3 mmol) was refluxed in 150 ml of a 5N sodium hydroxide aqueous solution for 15 minutes. The resulting liquid was neutralized to a pH of 9.0 using Amberlite IRC-50 (H+-type). Water was then added thereto to make the total volume 400 ml. To this was added 100 ml of carbon disulfide, and the mixture was reacted in an autoclave at a temperature of 120° C for a period of 5 hours under autogenous pressure (about 10 Kg/cm2). The orange colored substance thus formed was recovered followed by concentration to dryness. The residue was dissolved in 125 ml of 2.5N aqueous ammonia, and any impurities contained were filtered out. A mixture of n-butanol and acetic acid (250 ml:125 ml) was added to the filtrate to crystallize the product to obtain 16.5 g of 2-thioadenosine having a melting point of 198° C (with decomposition) in a 98% yield. UV Absorption Spectrum: maxpH 1 238.5 nm (ε:13800) and 293 nm (ε:18400); maxpH13 243 nm (ε:19100) and 283 nm (ε:14000).

Provenance & Evidence