Adenosine → HCID 136478604, compound

Participants

Reaction Steps

To a solution of 9-(2-deoxy-4-thio-α-D-ribofuranosyl)-2,6-diaminopurine (formula 8) (30 mg, 0.11 mmol) in distilled H2O (10 mL) was added a suspension of adenosine deaminase in 3.2M (NH4)2SO4 (0.1 mL) and reaction mixture was kept at room temperature. A 12-day TLC aliquot showed complete reaction. The solution was evaporated to dryness, the residue was crystallized from EtOH to give 9-(2-deoxy-4-thio-α-D-ribofuranosyl)-2-amino-1,6-dihydro-6-oxopurine (28 mg, 93%); mp 257°-260° C.; TLC 3: 1 CHCl3, MeOH, Rf 0.55; MS z/e 284 (M+1)+, UV λmax pH 1 254 (11.15), pH 7 254 (12.51), pH 13 267 (11.09); 1H NMR (Me2SO-d6, 300 MHz) δ2.30-2.40 (m, 1, H-2'), 2.52-2.62 (m, 1, H-2'), 3.30-3.40 (m, 1, H-5'), 3.46-3.58 (m, 1, H-5'), 3.60-3.66 (m, 1, H-4'), 4.46 (br t, 1, H-3'), 5.04 (br t, 1, 5'-OH), 5.50 (d, 1, 3'-OH, J=4 Hz), 5.94 (dd, 1, H-1', J=4 and 8 Hz), 6.50 (s, 2,NH2), 8.08 (s, 1, H-8); 13C NMR (Me2SO-d6, 300 MHz) δ42.57 (C-2'), 57.32 (C-1'), 59.63 (C-4'), 63.58 (C-5'), 74.34 (C-3'), 116.09 (C-5), 136.53 (C-8), 150.63 (C-4), 153.41 (C-2), 156.54 (C-6). Anal. (C10H13N5O3S) C, H, N, S.

Provenance & Evidence