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Abstract
Peracetylated 6-thioguanosine (2) undergoes the so far unknown N→S transglycosylation reaction to form a stable 9,S6 -bis(ribosyl) derivative (3) and N2-acetyl-6-thioguanine (4). The reaction takes place at elevated temperatures with no catalyst, or in solution in the presence of acidic catalysts. The reversible 7⇄9 isomerization, characteristic for guanosine and its analogs, has not been observed in this case.