Dimethyl Sulfoxide → 2'-O-Nonylguanosine

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Reaction Steps

A mixture of 2,6-diamino-9-(2-O-nonyl-β-D-ribofuranosyl)purine and 2,6-diamino-9-(3-O-nonyl-β-D-ribofuranosyl)purine (≈80:20 mixture, 29 g) in 0.1 M sodium phosphate buffer (50 ml, pH 7.4), 0.1 M tris buffer (1800 ml, pH 7.4) and DMSO (1080 ml) was treated with adenosine deaminase (1.6 g) as per the procedure of Example 3 to yield 60 g of product as an oil. An analytical product was purified by silica gel chromatography and recrystallized from EtOAc. m.p. 258-259° C. 1H NMR (DMSO-d6) δ 0.96 (t, 3, CH3, J=7 Hz); 1.17 [m, 12, O—CH2—CH2—(CH2)6]; 1.42 [m, 2, O—CH2CH2(CH2)6]; 3.27-3.61 (m, 4, H-5′, O—CH2(CH2)7]; 3.95 (m, 1, H-4′), 4.10-4.13 (m, 2, H-2′, H-3′); 5.13-6.06 (m, 2, 3′-OH5′-OH); 5.80 (d, 1, H-1′, J=6.4 Hz); 6.47 (s, 2, 2-NH2); 7.98 (s, 1, 8-H) and 10.64 (s, 1, N1 amide). Anal. Calcd. for C19H31N5O5: C, 55.73; H, 7.63; N, 17.10. Found: C, 55.67; H, 7.66; N, 17.02.

Provenance & Evidence