Potassium Hydroxide → Protoporphyrinogen IX

HRID 1071294Notes

Reaction equation

HRID 1071294 reaction equation
[Na].[CH3:2][C:3]1[C:21]([CH2:22][CH2:23][C:24]([OH:26])=[O:25])=[C:20]2[NH:27][C:4]=1[CH:5]=[C:6]1[N:10]=[C:9]([CH:11]=[C:12]3[C:37]([CH3:38])=[C:36]([CH:39]=[CH2:40])[C:14](=[CH:15][C:16]4[C:29]([CH3:30])=[C:28]([CH2:31][CH2:32][C:33]([OH:35])=[O:34])[C:18](=[CH:19]2)[N:17]=4)[NH:13]3)[C:8]([CH:41]=[CH2:42])=[C:7]1[CH3:43].[OH-].[K+].C1N(CCS(O)(=O)=O)CCOC1.O=C1O[C@H]([C@H](CO)O)C(O)=C1O>[Na].[Hg].[Hg].C(O)C>[CH3:2][C:3]1[C:21]([CH2:22][CH2:23][C:24]([OH:26])=[O:25])=[C:20]2[NH:27][C:4]=1[CH2:5][C:6]1[NH:10][C:9]([CH2:11][C:12]3[NH:13][C:14]([CH2:15][C:16]4[NH:17][C:18]([CH2:19]2)=[C:28]([CH2:31][CH2:32][C:33]([OH:35])=[O:34])[C:29]=4[CH3:30])=[C:36]([CH:39]=[CH2:40])[C:37]=3[CH3:38])=[C:8]([CH:41]=[CH2:42])[C:7]=1[CH3:43]

Participants

9

Reactant 5

HCID 14797Potassium HydroxideHCID 781654-Morpholineethanesulfonic acidHCID 5360545SodiumHCID 54670067L-Ascorbic AcidHCID 137797052HCID 137797052, compound2×

Product 1

HCID 121893Protoporphyrinogen IX

Reagents, catalysts & solvents 3

HCID 23931MercuryCatalystHCID 9837419Sodium amalgamCatalyst2×HCID 702EthanolSolvent

Procedure

The powder of sodium amalgam was prpared as follows. Into a round flask of 500 ml volume, 13 g of mercury and 0.5 g of thin-layer metal sodium were added, and equilibrated with nitrogen gas for 5 minutes, and it was shaked for 5 minutesthen. 8.4 g of protoporphyrin IX was dissolved into 10 mM KOH containing 15 ml of 20% ethanol, incubated at 4° C. To 4 ml of the protoporphyrin IX solution, equal amount of reaction mixture (0.1 M MES, 50 mM ascorbic acid) was added, and 16 mg of sodium amalgam freshly prepared was added, and shaken vigorously under nitrogen gas in a dark. The reaction mixture was filtered with a three-layer glass filter in a dark, and diluted 2.5 times with 0.1 M MES (pH4.5), and divided into 1 ml each in a light-shielded test tube and stored at −80° C.

Workup

  1. customincubated at 4° C
  2. additionwas added
  3. additionwas added
  4. filtrationThe reaction mixture was filtered with a three-layer glass
  5. filtrationfilter in a dark, and
  6. additiondiluted 2.5 times with 0.1 M MES (pH4.5)
  7. customdivided into 1 ml each in a light-shielded test tube
  8. customstored at −80° C.

Sources & evidence

ORD record
ord-b865741b62dd4c0cac24d1bedb17e17f
Source dataset
uspto-grants-2005_06
Patent number
US06905852B1

Reaction notes

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