Udp-Glucose → 3'-Azido-2',3'-Dideoxyuridine 5-O-Diphosphoglucose

HRID 467265

Reaction equation

HRID 467265 reaction equation
[CH2:1]1[C@H:5]([N:6]2[C:12](=[O:13])[NH:11][C:9](=[O:10])[CH:8]=[CH:7]2)[O:4][C@H:3]([CH2:14][OH:15])[C@H:2]1[N:16]=[N+:17]=[N-:18].[O-:19][P:20]([O:23][P:24]([O:27]P([O-])([O-])=O)([O-:26])=[O:25])(=[O:22])[O-:21].[CH2:32]([OH:47])[C@H:33]1[O:38][C@H:37](OP(O)(O)=O)[C@H:36]([OH:44])[C@@H:35]([OH:45])[C@@H:34]1[OH:46].[Mg+2].[Cl-].[Cl-].C(O)C(N)(CO)CO.Cl.C1C(=O)NC(=O)N([C@@H]2O[C@H](COP(OP(O[C@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)(O)=O)(O)=O)[C@@H](O)[C@H]2O)C=1.Cl(O)(=O)(=O)=O>>[N:16]([C@@H:2]1[C@@H:3]([CH2:14][OH:15])[O:4][C@@H:5]([N:6]2[CH:7]=[CH:8][C:9](=[O:10])[NH:11][C:12]2=[O:13])[CH2:1]1)=[N+:17]=[N-:18].[P:24]([O:27][C@H:33]([CH2:32][OH:47])[C@@H:34]([OH:46])[C@H:35]([OH:45])[C@@H:36]([OH:44])[CH:37]=[O:38])([O:23][P:20]([OH:21])([OH:19])=[O:22])([OH:26])=[O:25]

Participants

7

Reactant 6

HCID 8629Udp-GlucoseHCID 24247Perchloric AcidHCID 65533alpha-D-glucose 1-phosphateHCID 93573Tromethamine hydrochlorideHCID 5360315Magnesium ChlorideHCID 131717599AzddU triphosphate

Product 1

HCID 1317175983'-Azido-2',3'-Dideoxyuridine 5-O-Diphosphoglucose

Procedure

To 150 milligrams of AzddU-triphosphate was added 400 milligrams of glucose-1-phosphate, 6 millimole of MgCl2, 0.70 millimole of Tris-HCl pH 7.6, bacterial UDPG-pyrophosphorylase and inorganic pyrophosphatase. After 4 hours at room temperature, the reaction was stopped with perchloric acid (7N). After 30 minutes in ice, samples were centrifuged and the supernatant was neutralized with base. After another 30 minutes in ice, samples were recentrifuged and AzddU-5'-diphosphoglucose was purified by column chromatography.

Workup

  1. waitAfter 30 minutes in ice
  2. waitAfter another 30 minutes in ice
  3. customAzddU-5'-diphosphoglucose was purified by column chromatography

Sources & evidence

ORD record
ord-3cfdeae288a2409fb130096d830f42b3
Source dataset
uspto-grants-1992_10
Patent number
US05159067

Linked notes

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