Adenosine → 2'-O-(Imidazol-1-yl)butylguanosine

HRID 1066413Notes

Reaction equation

HRID 1066413 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:26][C@H:25]([CH2:27][OH:28])[C@@H:23]([OH:24])[C@H:12]2[O:13][CH2:14][CH2:15][CH2:16][CH2:17][N:18]2[CH:22]=[CH:21][N:20]=[CH:19]2)=[C:4](N)[N:3]=1.NC1N=C2C(N=CN2[C@@H]2O[C@H](CO)[C@@](CCCCN3C=CN=C3)(O)[C@H]2[OH:42])=C(N)N=1.[C@@H]1(N2C3N=CN=C(N)C=3N=C2)O[C@H](CO)[C@@H](O)[C@H]1O>CS(C)=O>[N:18]1([CH2:17][CH2:16][CH2:15][CH2:14][O:13][C@@H:12]2[C@H:23]([OH:24])[C@@H:25]([CH2:27][OH:28])[O:26][C@H:11]2[N:8]2[C:9]3[N:10]=[C:2]([NH2:1])[NH:3][C:4](=[O:42])[C:5]=3[N:6]=[CH:7]2)[CH:22]=[CH:21][N:20]=[CH:19]1

Participants

5

Reactant 3

HCID 60961AdenosineHCID 228747352,6-Diamino-9-[2-O-(imidazol-1-yl)butyl-beta-D-ribofuranosyl]purineHCID 867569922,6-diamino-9-[3'-(imidazol-1-yl)butyl-beta-D-ribofuranosyl]purine

Product 1

HCID 1360797852'-O-(Imidazol-1-yl)butylguanosine

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of the 2,6-diamino-9-[2′-O-(imidazol-1-yl)butyl-β-D-ribofuranosyl]purine and 2,6-diamino-9-[3′-(imidazol-1-yl)butyl-β-D-ribofuranosyl]purine isomers in 0.1 M tris buffer (pH 7.4), 0.1 M NaSO4 buffer (pH 7.4) and DMSO is treated with adenosine deaminase at RT for 5 days as per the procedure of Example 3. The product containing fractions are purified by silica gel chromatography and the product containing fraction evaporated to give the product.

Workup

  1. additionThe product containing fractions
  2. customare purified by silica gel chromatography
  3. additionthe product containing fraction
  4. customevaporated
  5. customto give the product

Sources & evidence

ORD record
ord-8d90d05e343144b487a4721e7209ab30
Source dataset
uspto-grants-2001_06
Patent number
US06242592B1

Reaction notes

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