Reaktion #55855

ord-69843a9b4f804ce7a10f54a4d2af355d

Reaktionsgleichung

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
CC=O
acetaldehyde
C[N+](C)(C)CC(=O)CC(=O)O.[Cl-]
dehydrocarnitine hydrochloride
→
C[N+](C)(C)C[C@H](O)CC(=O)[O-]
L-carnitine
Ausbeute 77.5%

Edukte

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
CC=O
acetaldehyde
C[N+](C)(C)CC(=O)CC(=O)O.[Cl-]
dehydrocarnitine hydrochloride
—
aldehyde

Reagenzien

Keine

Lösungsmittel

CC(=O)O
acetic acid

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

Carnitine was synthesized as in example 2, except that the NADH regeneration system comprised, in addition to alcohol dehydrogenase, aldehyde dehydrogenase (E.C. 1.2.1.5) which oxidizes the aldehyde (formed by action of alcohol dehydrogenase on ethanol) to acetic acid. Two molecules of NADH were formed from one molecule of ethanol (instead of one in the preceeding example) and the reaction balance was strongly displaced in favour of NADH and acetic acid formation. It was thus no longer necessary to eliminate acetaldehyde as in the preceeding example. The conditions were thus those of example 2, except that 125 units of purified aldehyde dehydrogenase (Boehringer ref. 171.832) were added to the reaction medium and nitrogen bubbling was omitted. After 24 hours, 0.764 g of L-carnitine was formed with a yield of 77.5% with respect to dehydrocarnitine hydrochloride.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04221869uspto-grants-1980_09