Adenosine → HCID 136205272, compound

HRID 1720544Notes

Reaction equation

HRID 1720544 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:22][C@H:21]([CH2:23][OH:24])[C@@H:19]([OH:20])[C@H:12]2[O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[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:28]>P([O-])([O-])([O-])=O.[Na+].[Na+].[Na+].CS(C)=O>[CH2:14]([O:13][C@@H:12]1[C@H:19]([OH:20])[C@@H:21]([CH2:23][OH:24])[O:22][C@H:11]1[N:8]1[C:9]2[N:10]=[C:2]([NH2:1])[NH:3][C:4](=[O:28])[C:5]=2[N:6]=[CH:7]1)[CH2:15][CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 2

HCID 60961AdenosineHCID 15858693HCID 15858693, compound

Product 1

HCID 136205272HCID 136205272, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 24243Trisodium PhosphateSolvent

Procedure

2,6-diamino-9-(2-O-pentyl-β-D-ribofuranosyl)purine (1.9 g) in 0.1M sodium phosphate buffer (50 ml, pH 6.0) and DMSO (25 ml) was treated with adenosine deaminase (added in two aliquots--first aliquot 50 mg, second aliquot 80 mg) at 35° C. as per the procedure of Example 3 to yield 1.4 g of product. 1H NMR (DMSO-d6) δ 0.8 (t, 3, CH3), 1.16 (m, 4, 2×CH2), 1.4 (m, 2, CH2), 3.38, 3.6 (m, 4, OCH2, H-5'), 3.93 (s, 1, H-4'), 4.28 (m, 2, H-2', H-3'), 5.17 (br, 2, 5', 3'-OH), 5.8 (d, 1, H-1'), 6.53 (br s, 2, NH2), 8.0 (s, 1, H-8) and 10.68 (br, 1, NH).

Sources & evidence

ORD record
ord-8a65f0f687b449779dd97ac82efaea83
Source dataset
uspto-grants-1996_04
Patent number
US05506351

Reaction notes

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