Adenosine → HCID 3001844, compound

Participants

Reaction Steps

A suspension of racemic synadenol (1, B=adenin-N9-yl, 200 mg, 0.92 mmol) from Example 5 in 0.05 M Na2HPO4 (pH 7.5, 100 mL) was briefly sonicated. Adenosine deaminase from calf intestine (Type II, Sigma Chemical Co., St. Louis, Mo., 30 mg, 45 units) was added and the mixture was stirred at room temperature. The progress of the reaction was followed by TLC in dichloromethane-methanol (9:1). The deamination stopped after 72 h and the ratio of synadenol (1, B=adenin-N9-yl): synhypoxanthol (1, B=hypoxanthin-N9-yl) was 7:3 as determined by UV spectrophotometry of the eluted spots. Addition of another two portions of enzyme (30 mg every 24 h) did not improve this ratio. The mixture was lyophilized and the resultant product was sonicated with several portions of dichloromethane-methanol (1:1, first 100 mL and then 40 mL) until no UV absorption was detectable in the solvent. The filtrate and washings were combined and evaporated. The residue was adsorbed on silica gel (4 g) and loaded on a column made of the same material. Chromatography using dichloromethane-methanol (9:1) as an eluent afforded (R)-(−)-synadenol (1, B=adenin-N9-yl), 135 mg, 66.5%), [α]25D−59.10 (c 0.04, MeOH) and elution with dichloromethane-methanol (4:1) gave (S)-(+)-synhypoxanthol (1, B=hypoxanthin-N9-yl), 85 mg, [α]25D 91.8° (c 0.1, MeOH).

Provenance & Evidence