Réaction #55853

ord-34f8bce2d0be46169f37fee9c1cb5f13

Équation de réaction

C[N+](C)(C)CC(=O)CC(=O)O.[Cl-]
dehydrocarnitine hydrochloride
NC(=O)C1=CN([C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)OC[C@H]3O[C@@H](n4cnc5c(N)ncnc54)[C@H](O)[C@@H]3O)[C@@H](O)[C@H]2O)C=CC1
NADH
→
C[N+](C)(C)C[C@H](O)CC(=O)[O-]
L-carnitine
Rendement 27.0%

Réactifs

C[N+](C)(C)CC(=O)CC(=O)O.[Cl-]
dehydrocarnitine hydrochloride
NC(=O)C1=CN([C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)OC[C@H]3O[C@@H](n4cnc5c(N)ncnc54)[C@H](O)[C@@H]3O)[C@@H](O)[C@H]2O)C=CC1
NADH

Réactifs

Aucun

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Mode opératoire

Carnitine dehydrogenase obtained as in example 1 was used in that synthesis. Synthesis of L-carnitine was carried out in the same conditions as in example 1, except as concerns the NADH regeneration system which was the yeast alcohol dehydrogenase and ethanol system instead of the glucose dehydrogenase and glucose system. Glucose was thus substituted with ethanol (concentration in the reactor: 4% by volume) and glucose dehydrogenase with 4 mg (700 units) of purified yeast alcohol dehydrogenase (Sigma ref. A 3263). Nitrogen was bubbled through the reactor (80 ml/mn) to eliminate the acetaldehyde formed by alcohol oxidation and thus improve the NADH regeneration. After 30 h, 0.325 g of L-carnitine was produced from dehydrocarnitine hydrochloride with a yield of 27%.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US04221869uspto-grants-1980_09