Acetic Acid → DL-Carnitine

Reaction equation

[CH:1]1[N:2]=[C:3]([NH2:44])[C:4]2[N:9]=[CH:8][N:7]([C@@H:10]3[O:14][C@H:13]([CH2:15][O:16][P:17]([O:20][P:21]([O:24][CH2:25][C@H:26]4[O:30][C@@H:29]([N:31]5[CH:36]=[C:35]([C:37]([NH2:39])=[O:38])[CH2:34][CH:33]=[CH:32]5)[C@H:28]([OH:40])[C@@H:27]4[OH:41])([OH:23])=[O:22])([OH:19])=[O:18])[C@@H:12]([OH:42])[C@H:11]3[OH:43])[C:5]=2[N:6]=1.[C:45]([OH:48])(=[O:47])[CH3:46].[CH2:49](O)C>>[OH:40][CH:28]([CH2:46][C:45](=[O:48])[O-:47])[CH2:29][N+:31]([CH3:49])([CH3:36])[CH3:32].[CH:1]1[N:2]=[C:3]([NH2:44])[C:4]2[N:9]=[CH:8][N:7]([C@@H:10]3[O:14][C@H:13]([CH2:15][O:16][P:17]([O:20][P:21]([O:24][CH2:25][C@H:26]4[O:30][C@@H:29]([N:31]5[CH:36]=[C:35]([C:37]([NH2:39])=[O:38])[CH2:34][CH:33]=[CH:32]5)[C@H:28]([OH:40])[C@@H:27]4[OH:41])([OH:23])=[O:22])([OH:19])=[O:18])[C@@H:12]([OH:42])[C@H:11]3[OH:43])[C:5]=2[N:6]=1

Participants

Reactant 3

HCID 176Acetic Acid

HCID 702Ethanol

HCID 439153Nadh

Product 2

HCID 288DL-Carnitine

HCID 439153Nadh

Procedure

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.