Adenosine → 2'-O-Methylguanosine

HRID 1720549Notes

Reaction equation

HRID 1720549 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@@H:11]2[O:18][C@H:17]([CH2:19][OH:20])[C@@H:15]([OH:16])[C@H:12]2[O:13][CH3:14])=[C:4](N)[N:3]=1.[C@@H]1(N2C3N=CN=C(N)C=3N=C2)O[C@H](CO)[C@@H](O)[C@H]1[OH:24]>P([O-])([O-])([O-])=O.[Na+].[Na+].[Na+].CS(C)=O>[CH3:14][O:13][C@@H:12]1[C@H:15]([OH:16])[C@@H:17]([CH2:19][OH:20])[O:18][C@H:11]1[N:8]1[C:9]2[N:10]=[C:2]([NH2:1])[NH:3][C:4](=[O:24])[C:5]=2[N:6]=[CH:7]1

Participants

5

Reactant 2

HCID 60961AdenosineHCID 99008052-Amino-2'-O-methyladenosine

Product 1

HCID 1354069502'-O-Methylguanosine

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 24243Trisodium PhosphateSolvent

Procedure

2,6-Diamino-9-(2-O-methyl-β-D-ribofuranosyl)purine (9.5 g) in 0.1M 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 C11H15N5O5.1/2H2O: C, 43.14; H, 5.26; N, 22.86. Found: C, 43.59; H, 5.34; N, 23.04.

Workup

  1. temperatureThe resulting suspension was cooled
  2. filtrationfiltered
  3. filtrationthe resulting filter cake
  4. washwashed with H2O
  5. dry with materialdried to a white solid (4.0 g)
  6. customThe solid was recrystallized from hot H2O

Sources & evidence

ORD record
ord-3b5c53006eb14e45a6da59d8e38ba188
Source dataset
uspto-grants-1996_04
Patent number
US05506351

Reaction notes

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