反応 #351898

反応方程式

sodium phosphate

adenosine

2,6-Diamino-9-(2'-O-propyl-β-D-ribofuranosyl) purine

2,6-Diamino-9-(3'-O-propyl-β-D-ribofuranosyl) purine

adenosine

→

product

2'-O-Propylguanosine

溶媒

DMSO

phosphate

DMSO

反応条件

後処理

1. 1
   workup.ADDITIONan addition 24 hrs
2. 2
   その他The solvent was evaporated in vacuo
3. 3
   その他the residue flash chromatographed on silica gel utilizing 5→20% MeOH/CH2Cl2
4. 4
   その他Product-containing fractions were evaporated in vacuo
5. 5
   その他the residue crystallized from H2O

実験手順

A mixture of 2,6-Diamino-9-(2'-O-propyl-β-D-ribofuranosyl) purine and 2,6-Diamino-9-(3'-O-propyl-β-D-ribofuranosyl) purine (4.6 gm) and adenosine deaminase (200 mg, Sigma Chemicals Type II) were stirred at room temperature overnight in 0.1M tris buffer (150 ml, pH 7.4), DMSO (100 ml) and 0.1M sodium phosphate buffer (10 ml). A further aliquot of adenosine deaminase (140 mg) in 0.1M phosphate buffer (30 ml) and DMSO (20 ml) was added and the reaction stirred an addition 24 hrs. The solvent was evaporated in vacuo and the residue flash chromatographed on silica gel utilizing 5→20% MeOH/CH2Cl2. Product-containing fractions were evaporated in vacuo and the residue crystallized from H2O to yield 2.6 gm of product. m.p. dec>270° C. 1H NMR (DMSO-d6) δ 0.75 (t, 3, CH3), 1.42 (tq, 2, CH2), 3.3-3.6 (m, 4, H-5', O--CH2), 3,85 (m, 1), 4.2 (m, 1), 4.23 (m, 1), 5.10 (t, 1, 5'-OH), 5.13 (d, 1, 3'-OH) 5.75 (d, 1, H-1') 6.45 (br s, 2, NH2), 7.95 (s, 1, H-8) and 10.67 (br s, 1, NH). Anal. Calcd. for C13H19N5O5 : C, 47.99; H, 5.89; N, 21.53. Found: C, 47.90, H, 5.85; N, 21.44.

出典