Reaktion #429095

Reaktionsgleichung

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

Lösungsmittel

DMSO

phosphate

DMSO

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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) δ0.75 (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.

Quelle