Abstract
The biosynthesis of carnitine in the rat was studied by following the metabolism of two radioactive derivatives of asialo-fetuin. The first contained 14C-labelled methyl groups covalently bound to the 6-N-amino fraction of its lysine residues as 6-N-monomethyl- and dimethyl-lysine. By treating this protein with iodomethane, a second derivative was produced in which the radioactivity was preferentially incorporated as 6-N-[Me-14C]-trimethyl-lysine. These desialylated glycoproteins, like other asialo-proteins, were immediately cleared from the blood by rat liver. Within hepatocyte lysosomes, the 14C-labelled proteins were rapidly hydrolysed, producing free amino acids containing the various 6-N-[Me-14C]methylated lysine residues. The radioactive amino acids crossed the lysosomal membrane and were further metabolized in the cytosol. Carnitine was the major radioactive metabolite detected in extracts of the rat carcass and liver after intravenous injection of 6-N-[Me-14C]trimethyl-lysine-labelled asialo-fetuin. Within 3h, at least 34.6% of the trimethyl-lysine in the administered protein was converted into carnitine. Similarly, an isolated perfused rat liver converted 30% of the added peptide-bound trimethyl-lysine into carnitine within 90 min. On the other hand, in numerous attempts we failed to detect radioactive carnitine in both rat liver and carcass between 20 min and 22 h after injection of 6-N-[Me-14C]-monomethyl- and -dimethyl-lysine-labelled asialo-fetuin. These data provide evidence for a pathway of carnitine biosynthesis that involves trimethyl-lysine as a peptide-bound precursor as proposed by R.A. Cox & C.L. Hoppel [(1973) Biochem. J. 136, 1083-1090] and V. Tanphaichitr & H.P. Broquist [(1973) J. Biol. Chem. 248, 2176-2181]. The findings also show that rat liver can synthesize carnitine without the aid of other tissues, but cannot convert free partially methylated lysines into trimethyl-lysine.
MeSH Terms
Amino Acids/analysis
Animals
Carnitine/biosynthesis,isolation & purification
Liver/metabolism
Lysine/analogs & derivatives
Lysosomes/metabolism
Metabolic Clearance Rate
Rats
alpha-Fetoproteins/metabolism
Chemicals
Amino Acids
alpha-Fetoproteins
Lysine
Carnitine
Authors & Affiliations
3 authors, click to expand affiliations / ORCID
LaBadie J
Dunn W A
Aronson N N
References (18)
18 references, click to expand
-
Protein methylation: chemical, enzymological, and biological significance.
Adv Enzymol Relat Areas Mol Biol. 1975;42:227-86
PMID: 1093364
-
Biological methylation: selected aspects.
Annu Rev Biochem. 1975;44:435-51
PMID: 1094914
-
Turnover of carnitine by rat tissues.
Biochem J. 1975 Jun;148(3):439-45
PMID: 1200987
-
Role of lysine and -N-trimethyllysine in carnitine biosynthesis. I. Studies in Neurospora crassa.
J Biol Chem. 1973 Mar 25;248(6):2170-5
PMID: 4266139
-
Presence and location of an unusual amino acid, epsilon-N-trimethyllysine, in cytochrome c of wheat germ and Neurospora.
J Biol Chem. 1969 Mar 10;244(5):1385-8
PMID: 4304194
-
Epsilon-alkyllysinase. New assay method, purification, and biological significance.
Arch Biochem Biophys. 1974 Nov;165(1):369-78
PMID: 4441079
-
The role of surface carbohydrates in the hepatic recognition and transport of circulating glycoproteins.
Adv Enzymol Relat Areas Mol Biol. 1974;41(0):99-128
PMID: 4609051
-
Role of lysine and -N-trimethyllysine in carnitine biosynthesis. II. Studies in the rat.
J Biol Chem. 1973 Mar 25;248(6):2176-81
PMID: 4690599
-
Inhibition of gluconeogenesis in the isolated perfused rat liver by -phenylalkanoic acids.
J Biol Chem. 1973 Apr 10;248(7):2514-20
PMID: 4698229
-
Biosynthesis of carnitine and 4-N-trimethylaminobutyrate from lysine.
Biochem J. 1973 Dec;136(4):1075-82
PMID: 4786529
-
Biosynthesis of carnitine and 4-N-trimethylaminobutyrate from 6-N-trimethyl-lysine.
Biochem J. 1973 Dec;136(4):1083-90
PMID: 4786530
-
Carnitine synthesis in rat tissue slices.
Biochem Biophys Res Commun. 1974 Feb 4;56(3):676-81
PMID: 4826875
-
Role of lysine in carnitine biosynthesis in Neurospora crassa.
J Biol Chem. 1971 Jul 10;246(13):4373-5
PMID: 5090046
-
Lysine, a precursor of carnitine in the rat.
J Biol Chem. 1971 Oct 25;246(20):6364-6
PMID: 5127431
-
Identification of epsilon-N-monomethyllysine and epsilon-N-trimethyllysine in rabbit skeletal myosin.
Biochem Biophys Res Commun. 1969 Sep 24;37(1):59-65
PMID: 5346361
-
Isolation and identification of N-G,N-G- and N-G,N'-G-dimethyl-arginine, N-epsilon-mono-, di-, and trimethyllysine, and glucosylgalactosyl- and galactosyl-delta-hydroxylysine from human urine.
J Biol Chem. 1970 Nov 10;245(21):5751-8
PMID: 5472370
-
Reductive alkylation of amino groups in proteins.
Biochemistry. 1968 Jun;7(6):2192-201
PMID: 5690712
-
Glycoprotein catabolism in rat liver: Lysosomal digestion of iodinated asialo-fetuin.
Biochem J. 1975 Nov;152(2):271-9
PMID: 56934