Adenosine → 9-(2-Deoxy-4-C-ethynyl-beta-D-ribo-pentofuranosyl)guanine

HRID 2186326Notes

Reaction equation

C(O)C(N)(CO)C[OH:4].Cl.[NH2:10][C:11]1[N:19]=[C:18]2[C:14]([N:15]=[CH:16][N:17]2[C@@H:20]2[O:25][C@:24]([C:28]#[CH:29])([CH2:26][OH:27])[C@@H:22]([OH:23])[CH2:21]2)=[C:13](N)[N:12]=1.[C@@H]1(N2C3N=CN=C(N)C=3N=C2)O[C@H](CO)[C@@H](O)[C@H]1O>O>[C:28]([C@:24]1([CH2:26][OH:27])[O:25][C@@H:20]([N:17]2[C:18]3[N:19]=[C:11]([NH2:10])[NH:12][C:13](=[O:4])[C:14]=3[N:15]=[CH:16]2)[CH2:21][C@@H:22]1[OH:23])#[CH:29]

Participants

Conditions

Temperature: 40 °C

Procedure

To a Tris-HCl buffer solution (7.8 ml, pH 7.5) of Compound 28 (0.03 g, 0.103 mmol), adenosine deaminase (0.057 ml, 20 unit) was added, and the mixture was stirred for 2 hours at 40° C., followed by cooling to room temperature. The reaction mixture was applied to a reverse-phase ODS silica gel column (50 g), desalted by water (500 ml) flow, and through use of aqueous 2.5% ethanol, Compound 30 was eluted. Recrystallization from water yielded Compound 30 in an amount of 0.015 g (50%).

Workup

temperatureby cooling to room temperature
washthrough use of aqueous 2.5% ethanol, Compound 30 was eluted
customRecrystallization from water yielded Compound 30 in an amount of 0.015 g (50%)

Sources & evidence

ORD record: ord-a430769476364bb78b6396575fe4c4f7
Source dataset: uspto-grants-2002_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06403568B1

Reaction notes

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