4-(2′-Carboxyphenyl)-4-oxobutyryl Coenzyme A Ester, an Intermediate in Vitamin K2 (Menaquinone) Biosynthesis

Abstract

Enzyme preparations from Mycobacterium phlei, Escherichia coli and Galium mollugo cell suspension cultures were incubated in the presence of 4-(2′-carboxyphenyl)-4-oxobutyrate (i.e. o- succinylbenzoic acid. OSB. 1). ATP. coenzyme A and Mg2+. The main product isolated from the incubation mixture was 4-(2′-carboxyphenyl)-4-oxobutyryl coenzyme A ester (2) as determined by comparison with synthetic coenzyme A esters. Synthetic and enzymically formed 4-(2′-car-boxyphenyl)-4-oxobutyryl coenzyme A ester (2) was shown to be enzymically converted to an intermediate in vitamin K2 biosynthesis viz. 1.4-dihydroxy-2′-naphthoic acid (5). The enzymic formation of 2-(3′-Carboxypropionyl)benzoyl coenzyme A ester (3) and 4-(2′-carboxyphenyl)-4-oxobutyryl-di-coenzyme A ester (4) was also observed. They appeared in minor amounts, how­ever. These esters were not convertible to 1.4-dihydroxy-2-naphthoic acid (5).