Adenosine → 4'-Thio-2',3'-dideoxyguanosine

Participants

Reaction Steps

To a solution of 17 (50 mg, 0.18 mmol) in 20 mL of a 0.75 M TEAB buffer was added 6 μL of adenosine deaminase. The reaction was stirred for 12 days followed by lyophilization. The residue was purified by preparative TLC with 4:1 CHCl3 -MeOH. The crude product was recrystallized from hot EtOH to give 19 (40 mg, 80%); mp. 180°-183° C., FAB MS 268 (M+H)+ ; 1H NMR (DMSO-d6) δ 10.8 (br, 1, NH), 8.0 (s, 1, H-8), 6.6 (s, 2, NH2), 5.90 (m, 1, 1'-H), 5.12 (brs, 1, 5'-OH), 3.72 (m, 1, 4'-H), 3.55 (m, 2, 5'-H), 2.35 (m, 2, 2'-H), 2.15 (m, 1, 3'-H), 1.95 (m, 1, 3'-H).

Provenance & Evidence