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The synthesis and biological activity of thiolcarnitine and its thiolesters
Author(s) -
Duhr Edward F.,
Mauro J. Matthew,
Clennan Edward L.,
Barden Roland E.
Publication year - 1983
Publication title -
lipids
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.601
H-Index - 120
eISSN - 1558-9307
pISSN - 0024-4201
DOI - 10.1007/bf02537236
Subject(s) - acetylcarnitine , carnitine , hydrolysis , chemistry , substrate (aquarium) , acetyl coa , catalysis , acylation , base (topology) , coenzyme a , medicinal chemistry , stereochemistry , organic chemistry , enzyme , biochemistry , biology , ecology , mathematical analysis , mathematics , reductase
Acetyl‐D,L‐thiolcarnitine was synthesized by the acid‐catalyzed addition of thiolacetic acid to 4‐trimethylammonio‐2‐butenoic acid. Acetyl‐D,L‐thiolcarnitine was the precursor of D,L‐thilcarnitine, which was prepared by base hydrolysis. Thiolcarnitine significantly enriched in the L‐isomer was prepared from acetyl‐D,L‐thiolcarnitine using carnitine acetyltransferase as the resolving agent. The C 2 , C 8 and C 16 carnitine thiolesters were obtained by acylating thiolcarnitine with the corresponding N‐hydroxysuccinimide esters. As a substrate for carnitine acetyltransferase, acetylthiolcarnitine gave the same kinetic constants as did acetylcarnitine; on the other hand, thiolcarnitine and carnitine gave the same K m but the V max with thiolcarnitine was less than 5% of the value obtained with carnitine. With thiolcarnitine and acetylthiolcarnitine as reactants, the measured K eq , at 30 C and pH 7.0, for the reaction catalyzed by carnitine acetyltransferase (see below) was 4.6±.1. acetylthiolcarnitine+CoA—acetyl‐CoA+thiolcarnitine