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

HRID 1416705Notes

Reaction equation

HRID 1416705 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@@H](OCCCCN3C=CN=C3)[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 228747382,6-diamino-9-[3-O-(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'-O-(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-06a5a031be7a4ae2bbac768287b99833
Source dataset
uspto-grants-1999_06
Patent number
US05914396

Reaction notes

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