Phosphate → NADPH

HRID 1359124Notes

Reaction equation

HRID 1359124 reaction equation
[CH:1]1[CH:6]=[N+:5]([C@@H:7]2[O:11][C@H:10]([CH2:12][O:13][P:14]([O:17][P:18]([O:21][CH2:22][C@H:23]3[O:27][C@@H:26]([N:28]4[C:32]5[N:33]=[CH:34][N:35]=[C:36]([NH2:37])[C:31]=5[N:30]=[CH:29]4)[C@H:25]([O:38][P:39]([OH:42])([OH:41])=[O:40])[C@@H:24]3[OH:43])([OH:20])=[O:19])([OH:16])=[O:15])[C@@H:9]([OH:44])[C@H:8]2[OH:45])[CH:4]=[C:3]([C:46]([NH2:48])=[O:47])[CH:2]=1.P([O-])([O-])([O-])=O.[OH-].[Na+]>>[CH:34]1[N:35]=[C:36]([NH2:37])[C:31]2[N:30]=[CH:29][N:28]([C@@H:26]3[O:27][C@H:23]([CH2:22][O:21][P:18]([O:17][P:14]([O:13][CH2:12][C@H:10]4[O:11][C@@H:7]([N:5]5[CH:4]=[C:3]([C:46]([NH2:48])=[O:47])[CH2:2][CH:1]=[CH:6]5)[C@H:8]([OH:45])[C@@H:9]4[OH:44])([OH:16])=[O:15])([OH:20])=[O:19])[C@@H:24]([OH:43])[C@H:25]3[O:38][P:39]([OH:42])([OH:41])=[O:40])[C:32]=2[N:33]=1

Participants

4

Reactant 3

HCID 1061PhosphateHCID 5886NADP nicotinamide-adenine-dinucleotide phosphateHCID 14798Sodium Hydroxide

Product 1

HCID 5884NADPHYield 61.7%

Conditions

Temperature
40 °C

Procedure

NADP+ (36.0 mg, 47.0 μmol) was placed in 2 mL of a 0.1 M phosphate buffer. The pH of this solution was adjusted to 8.3 with NaOH and then placed in an 80 mL Fisher-Porter bottle. The Fisher-Porter bottle was evacuated and refilled with argon three times then [Cl2Ru(TPPTS)2]2 (9.7 mg, 3.7 μmol) was added under a flow of argon. The Fisher-Porter bottle was evacuated and filled with 70 psi of H2 and heated to 40° C. for 3.0 hr. The volatiles were removed under reduced pressure and a sample dissolved in D2O. To this was added 20 μl of trimethylsilylpropionate standard solution. 1H NMR integration shows that 29.0 μmole of NADPH have been produced under these conditions.

Workup

  1. customThe Fisher-Porter bottle was evacuated
  2. additionrefilled with argon three times
  3. customThe Fisher-Porter bottle was evacuated
  4. additionfilled with 70 psi of H2
  5. customThe volatiles were removed under reduced pressure
  6. dissolutiona sample dissolved in D2O
  7. additionTo this was added 20 μl of trimethylsilylpropionate standard solution

Sources & evidence

ORD record
ord-03e5a5006b2c43be931a84a7e0879ecb
Source dataset
uspto-grants-2003_07
Patent number
US06599723B1

Reaction notes

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