Dimethyl Sulfoxide → 2'-O-Octadecylguanosine

Participants

Reaction Steps

2,6-Diamino-9-(2-O-octadecyl-β-D-ribofuranosyl) purine (10 g) in 0.1M sodium phosphate buffer (50 ml, pH 7.4), 0.1M tris buffer (1000 ml, pH 7.4) and DMSO (1000 ml) was treated with adenosine deaminase (1.5 g) at RT. At day 3, day 5 and day 7 an additional aliquot (500 mg, 880 mg and 200 mg, respectively) of adenosine deaminase was added. The reaction was stirred for a total of 9 day and purification by silica gel chromatography yielded the product (2 g). An analytical sample was recrystallized from MeOH. 1H NMR (DMSO-d6) δ 0.84 (t, 3, CH3), 1.22 (s, 32, O--CH2 --CH2 --(CH2)16), 5.07 (m, 2,3'-OH and 5'-OH), 5.78 (d, 1,1'H), 6.43 (s, 2, NH2), 7.97 (s, 1,8 H) and 10.64 (s, 1, NH2). Anal. Calcd. for C28H49N5O5 : C, 62.80; H, 9.16; N, 12.95. Found: C, 62.54; H, 9.18; N, 12.95.

Provenance & Evidence