(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal → Ribosylthymidine diphosphate

HRID 1856592Notes

Reaction equation

HRID 1856592 reaction equation
[P:1]([O:13][CH2:14][C@H:15]1[O:19][C@@H:18]([N:20]2[CH:27]=[C:26]([CH3:28])[C:24](=[O:25])[NH:23][C:21]2=[O:22])[C@H:17]([OH:29])[C@@H:16]1[OH:30])([O:4][P:5]([O:8]P(O)(O)=O)([OH:7])=[O:6])(=[O:3])[OH:2].O=C[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O.[O-]P(OP([O-])([O-])=O)(=O)[O-].[O-]P(OP(OP([O-])([O-])=O)([O-])=O)(=O)[O-]>C(O)C(N)(CO)CO.S([O-])([O-])(=O)=O.[NH4+].[NH4+]>[P:1]([O:13][CH2:14][C@H:15]1[O:19][C@@H:18]([N:20]2[CH:27]=[C:26]([CH3:28])[C:24](=[O:25])[NH:23][C:21]2=[O:22])[C@H:17]([OH:29])[C@@H:16]1[OH:30])([O:4][P:5]([OH:8])([OH:7])=[O:6])(=[O:2])[OH:3]

Participants

7

Reactant 4

HCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanalHCID 4513885-Methyluridine 5'-triphosphateHCID 644102Pyrophosphate2×HCID 3440921Triphosphate2×

Product 1

HCID 23379797Ribosylthymidine diphosphate

Reagents, catalysts & solvents 2

HCID 6503Tris(hydroxymethyl)aminomethaneSolvent2×HCID 6097028Ammonium SulfateSolvent

Procedure

5-Methyluridine 5'-triphosphate (0.0047 g, 0.009 mMol) was dissolved in 0.7 mL 1M Tris buffer (pH 8.5 containing 1M MgCl2) then 0.3 mL of a 0.25M glucose solution in 1M Tris buffer (pH 8.5 containing 1M MgCl2) added. A To timepoint was taken by reverse phase anion exchange HPLC. Hexokinase (EC 2.7.1.1, Boehringer Mannheim, from yeast overproducer), 75 units in 3.2M ammonium sulfate suspension, was added to the reaction which was incubated at 25° C. An HPLC was taken at 66 hours indicating complete conversion to diphosphate with no triphosphate remaining. Triphosphate retention: 17.5 minutes; diphosphate retention: 10.3 minutes.

Workup

  1. customwas incubated at 25° C
  2. custom17.5 minutes
  3. custom10.3 minutes

Sources & evidence

ORD record
ord-6b74d2aa04b24b3ab82843ee73c9f71e
Source dataset
uspto-grants-2000_11
Patent number
US06143279

Reaction notes

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