Synthesis, Analysis and Characterization of the Coenzyme A Esters of 0-SuccinyIbenzoic Acid, an Intermediate in Vitamin K2 (Menaquinone) Biosynthesis
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چکیده
Rainer Kolkmann and Eckhard Leistner Institut für Pharmazeutische Biologie, Rheinische Friedrich-Wilhelms-Universität, D-5300 Bonn, Bundesrepublik Deutschland Z. Naturforsch. 42c, 542-552 (1987); received October 27, 1986/January 19, 1987 o-Succinylbenzoic Acid Coenzyme A Ester, 1,4-Dihydroxy-2-naphthoic Acid, Menaquinone, Vitamin K, Biosynthesis One of the carboxyl groups of o-succinylbenzoic acid (OSB, 1) is activated during the biosyn thesis of vitamin K2 and anthraquinones. In an attempt to determine the exact structure of the naturally occurring OSB coenzyme A thioester, the three possible esters were prepared via the imidazolides of OSB. HPLC systems were developed for the successful separation of the esters and their structural analogues. The structures of the coenzyme A esters were investigated and their products of hydrolysis determined quantitatively. Two of the esters were highly labile at pH 7 and 30 °C. UV spectroscopy is a suitable method to distinguish between different positions of activation. Fast atom bombardment mass spectrometry was successfully employed to charac terize two of the esters. The data strongly indicate that the “aliphatic” coenzyme A ester is the intermediate in vitamin K2 and anthraquinone biosynthesis.
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