Acetic Acid → L-Ornithine, acetate (1:1)

HRID 742183

Reaction equation

HRID 742183 reaction equation
[O:1]=[C:2]1[O:8][C@H]([C@H](CO)O)C(O)=[C:3]1O.[NH2:13][C@H:14]([C:22]([OH:24])=[O:23])[CH2:15][CH2:16][CH2:17][NH:18]C(=N)N.C(O)(=O)C>O.S([O-])([O-])(=O)=O.[Mn+2].O>[C:2]([OH:8])(=[O:1])[CH3:3].[NH2:13][C@H:14]([C:22]([OH:24])=[O:23])[CH2:15][CH2:16][CH2:17][NH2:18]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 54670067L-Ascorbic AcidHCID 178418600HCID 178418600, compound

Product 1

HCID 6453938L-Ornithine, acetate (1:1)

Reagents, catalysts & solvents 2

HCID 177577Manganese sulfate monohydrateCatalystHCID 962WaterSolvent

Procedure

42.3 mg manganese sulfate hydrate (2.5×10-4 molar), 21.8 mg ascorbic acid (1.25×10-4 molar) and 15000 units calf's liver arginase of the Boehringer Mannheim company were added to 1 liter of a 0.75 molar L-arginine solution. After 48 hours the conversion was 100% according to HPLC. The mixture was adjusted with acetic acid to pH 6.8, three quarters of the water drawn off and the ornithine acetate precipitated with one liter ethanol at room temperature. After 15 min. of postagitation the precipitate was filtered off, postwashed with ethanol and dried in a vacuum (40 mbars). The yield of pure ornithine acetate was 137.0 g, 95% of theory). Amount of rotation (c=5 in water)+10.0° (theoretical: +9.0 to +11.0).

Workup

  1. customthe ornithine acetate precipitated with one liter ethanol at room temperature
  2. filtrationAfter 15 min. of postagitation the precipitate was filtered off
  3. customdried in a vacuum (40 mbars)
  4. customAmount of rotation (c=5 in water)+10.0° (theoretical: +9.0 to +11.0)

Sources & evidence

ORD record
ord-6afb7c5b38e84213b013130b0ea89f0f
Source dataset
uspto-grants-1996_09
Patent number
US05554518

Linked notes

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