Abstract
Synthesis of l-carnitine has been carried out by the enzymatic reduction of the carbonyl group of the achiral precursor 3-dehydrocarnitine with the oxidized nicotinamide adenine dinucleotide-linked carnitine dehydrogenase. Various enzymatic or chemical systems have been tested to regenerate the reduced nicotinamide adenine dinucleotide oxidized in the reduction of 3-dehydrocarnitine. Because of the instability of this compound in aqueous solutions, it was added by continuous feeding as a rate-limiting constituent in the reaction mixture. Under these conditions, conversion yields of 95% were achieved with the glucose plus glucose dehydrogenase system. A total number of 530 reduced nicotinamide adenine dinucleotide recyclings was obtained with this system for a production of 45 g of l-carnitine per liter. The stabilities of the oxidized nicotinamide adenine dinucleotide and the reduced nicotinamide adenine dinucleotide have been determined at various pH values. In view of these results, several possible strategies for enzymatic syntheses with the reduced nicotinamide adenine dinucleotide as a regenerable coenzyme are discussed.
Full text
PDF







Selected References
These references are in PubMed. This may not be the complete list of references from this article.
- Aurich H., Kleber H. P., Schöpp W. D. An inducible carnitine dehydrogenase from Pseudomonas aeruginosa. Biochim Biophys Acta. 1967 Jul 11;139(2):505–507. doi: 10.1016/0005-2744(67)90054-x. [DOI] [PubMed] [Google Scholar]
- Aurich H., Kleber H. P., Sorger H., Tauchert H. Reinigung und Eigenschaften der Carnitindehydrogenase aus Pseudomonas aeruginosa. Eur J Biochem. 1968 Nov;6(2):196–201. doi: 10.1111/j.1432-1033.1968.tb00437.x. [DOI] [PubMed] [Google Scholar]
- Aurich H., Schöpp W. D., Strack E., Focke G. Darstellung von 3-Dehydro-carnitin. Hoppe Seylers Z Physiol Chem. 1968 Oct;349(10):1310–1312. [PubMed] [Google Scholar]
- Chibata I., Tosa T., Sato T. Immobilized aspartase-containing microbial cells: preparation and enzymatic properties. Appl Microbiol. 1974 May;27(5):878–885. doi: 10.1128/am.27.5.878-885.1974. [DOI] [PMC free article] [PubMed] [Google Scholar]
- FRITZ I. B. CARNITINE AND ITS ROLE IN FATTY ACID METABOLISM. Adv Lipid Res. 1963;1:285–334. [PubMed] [Google Scholar]
- Gestrelius S., Månsson M. O., Mosbach K. Preparation of an alcohol-dehydrogenase--NAD(H)--sepharose complex showing no requirement of soluble coenzyme for its activity. Eur J Biochem. 1975 Sep 15;57(2):529–535. doi: 10.1111/j.1432-1033.1975.tb02328.x. [DOI] [PubMed] [Google Scholar]
- Hermann M., Thevenet N. J., Coudert-Maratier M. M., Vandecasteele J. P. Consequences of lysine oversynthesis in Pseudomonas mutants insensitive to feedback inhibition. Lysine excretion or endogenous induction of a lysine-catabolic pathway. Eur J Biochem. 1972 Oct 17;30(1):100–106. doi: 10.1111/j.1432-1033.1972.tb02076.x. [DOI] [PubMed] [Google Scholar]
- Kleber H. P., Schöpp W., Sorger H., Tauchert H., Aurich H. Bildung von 3-Dehydrokarnitin aus L-Karnitin durch ein Enzym aus Pseudomonas aeruginosa. Acta Biol Med Ger. 1967;19(5):659–667. [PubMed] [Google Scholar]
- Mosbach K., Larsson P. O., Lowe C. Immobilized coenzymes. Methods Enzymol. 1976;44:859–887. doi: 10.1016/s0076-6879(76)44063-6. [DOI] [PubMed] [Google Scholar]
- Månsson M. O., Larsson P. O., Mosbach K. Recycling by a second enzyme of NAD covalently bound to alcohol dehydrogenase. FEBS Lett. 1979 Feb 15;98(2):309–313. doi: 10.1016/0014-5793(79)80206-9. [DOI] [PubMed] [Google Scholar]
- Nakazawa H., Enei H., Okumura S., Yoshida H., Yamada H. Enzymatic preparation of L-tryptophan and 5-hydroxy-L-tryptophan. FEBS Lett. 1972 Sep 1;25(1):43–45. doi: 10.1016/0014-5793(72)80449-6. [DOI] [PubMed] [Google Scholar]
- ROBINSON D. S. OXIDATION OF SELECTED ALKANES AND RELATED COMPOUNDS BY A PSEUDOMONAS STRAIN. Antonie Van Leeuwenhoek. 1964;30:303–316. doi: 10.1007/BF02046736. [DOI] [PubMed] [Google Scholar]
- STERN J. R., COON M. J., DEL CAMPILLO A. Enzymes of fatty acid metabolism. III. Breakdown and synthesis of beta-keto fatty acids. J Biol Chem. 1956 Jul;221(1):1–14. [PubMed] [Google Scholar]
- STRACK E., AURICH H., GRUENER E. UBER DIE ABBAUFAEHIGKEIT BESTIMMTER PSEUDOMONAS-SPECIES FUER (-)-CARNITIN. Z Allg Mikrobiol. 1964;4:154–160. doi: 10.1002/jobm.3630040208. [DOI] [PubMed] [Google Scholar]
