Adenosine → 4'-Thio-2',3'-dideoxyguanosine

HRID 653986Notes

Reaction equation

HRID 653986 reaction equation
[CH:1]1([N:8]2[CH:16]=[N:15][C:14]3[C:9]2=[N:10][C:11]([NH2:18])=[N:12][C:13]=3N)[S:5][C@H:4]([CH2:6][OH:7])[CH2:3][CH2:2]1.[C@@H]1(N2C3N=CN=C(N)C=3N=C2)O[C@H](CO)[C@@H](O)[C@H]1[OH:21]>CC[N+](CC)(CC)CC.[Br-]>[C@@H:1]1([N:8]2[C:9]3[N:10]=[C:11]([NH2:18])[NH:12][C:13](=[O:21])[C:14]=3[N:15]=[CH:16]2)[S:5][C@H:4]([CH2:6][OH:7])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 60961AdenosineHCID 44366862HCID 44366862, compound

Product 1

HCID 1355386974'-Thio-2',3'-dideoxyguanosineYield 80%

Reagents, catalysts & solvents 1

HCID 6285Tetraethylammonium BromideCatalyst

Procedure

To a solution of 17 (50 mg, 0.18 mmol) in 20 mL of a 0.75 M TEAB buffer was added 6 μL of adenosine deaminase. The reaction was stirred for 12 days followed by lyophilization. The residue was purified by preparative TLC with 4:1 CHCl3 -MeOH. The crude product was recrystallized from hot EtOH to give 19 (40 mg, 80%); mp. 180°-183° C., FAB MS 268 (M+H)+ ; 1H NMR (DMSO-d6) δ 10.8 (br, 1, NH), 8.0 (s, 1, H-8), 6.6 (s, 2, NH2), 5.90 (m, 1, 1'-H), 5.12 (brs, 1, 5'-OH), 3.72 (m, 1, 4'-H), 3.55 (m, 2, 5'-H), 2.35 (m, 2, 2'-H), 2.15 (m, 1, 3'-H), 1.95 (m, 1, 3'-H).

Workup

  1. customThe residue was purified by preparative TLC with 4:1 CHCl3 -MeOH
  2. customThe crude product was recrystallized from hot EtOH

Sources & evidence

ORD record
ord-573f060139fa47b5a8d62f1120278eb9
Source dataset
uspto-grants-1992_07
Patent number
US05128458

Reaction notes

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