Carnitine Chloride → (-)-Carnitine

HRID 579937

Reaction equation

HRID 579937 reaction equation
[CH3:1][N+:2]([CH2:5][CH:6]([OH:11])[CH2:7][C:8]([O-:10])=[O:9])([CH3:4])[CH3:3].Cl.O[C@@H](CC(=O)[O-])C[N+](C)(C)C.[Cl-]>>[OH:11][C@H:6]([CH2:7][C:8](=[O:9])[O-:10])[CH2:5][N+:2]([CH3:4])([CH3:1])[CH3:3]

Participants

4

Procedure

The procedure of Example 2c was followed except that the concentration of DL-carnitine chloride for the F-2 stage was 50 g/l, which consisted of 3 parts of L-carnitine chloride and 7 parts D-carnitine chloride in 250 ml of medium B held in a two liter Erlenmeyer flask. After incubation with A. calcoaceticus ATCC 39647 for 69 hours (F-2 stage), 50 ml of the broth was centrifuged (9000×6 for 20 minutes) to remove the cells. The supernatant was evaporated to dryness in vacuo and the residue was extracted with anhydrous ethanol. The ethanolic extract was concentrated to dryness and the residue was dissolved in distilled water and chromatographed over a Dowex 1-X-4 OH column (5×22 cm) to obtain L-carnitine [140 mg (23% yield), [α]D25 -29.2°, c, 1.5 H2O].

Workup

  1. custom(9000×6 for 20 minutes) to remove the cells
  2. customThe supernatant was evaporated to dryness in vacuo
  3. extractionthe residue was extracted with anhydrous ethanol
  4. extractionThe ethanolic extract
  5. concentrationwas concentrated to dryness
  6. dissolutionthe residue was dissolved in distilled water
  7. customchromatographed over a Dowex 1-X-4 OH column (5×22 cm)

Sources & evidence

ORD record
ord-34bc61fdcaf042888df96ba2ba0966ea
Source dataset
uspto-grants-1988_06
Patent number
US04751182

Linked notes

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