Adenosine → 2'-O-Methylguanosine

Participants

Reaction Steps

2,6-Diamino-9-(2-O-methyl-β-D-ribofuranosyl)purine (9.5 g) in 0.1 M sodium phosphate buffer (200 ml, pH 7.4) and DMSO (25 ml) was treated with adenosine deaminase (Type II Sigma) at RT for 4 days. The resulting suspension was cooled and filtered and the resulting filter cake washed with H2O and dried to a white solid (4.0 g). The solid was recrystallized from hot H2O to yield 2.9 g of product. m.p. 236-238° C. 1H NMR (DMSO-d6) δ 3.3 (s, 3, OCH3), 3.53 and 3.6 (ABX, 2, H-5′), 3.87 (m, 1, H-4′), 4.15 (m, 1, H-2′), 4.25 (m, 1, H-3′), 5.13 (t, 1, 5′-OH), 5.23 (d, 1, 3′-OH), 5.8 (d, 1, H-1′), 6.48 (br s, 2, NH2), 7.96 (s, 1, H-8) and 10.68 (br s, 1, NH). Anal. Calcd. for C11H15N5O5.½H2O: C, 43.14; H, 5.26; N, 22.86. Found: C, 43.59; H, 5.34; N, 23.04.

Provenance & Evidence