4-(2'-Carboxyphenyl)-4-oxobutyryl coenzyme A ester, an intermediate in vitamin K2 (menaquinone) biosynthesis.
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'-carboxyphenyl)-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).
Kolkmann
R
R
Institut für Pharmazeutische Biologie, Rheinische Friedrich-Wilhelms-Universität Bonn, Bundesrepublik Deutschland.
Leistner
E
E
D000214:Acyl Coenzyme A / Q000378:metabolism*; D055598:Chemical Phenomena; D002621:Chemistry; D002851:Chromatography, High Pressure Liquid; D004926:Escherichia coli / Q000201:enzymology*; D004952:Esters; D006863:Hydrogen-Ion Concentration; D009161:Mycobacterium / Q000201:enzymology*; D009168:Mycobacterium phlei / Q000201:enzymology*; D010944:Plants / Q000201:enzymology*; D014812:Vitamin K / Q000096:biosynthesis*
D000214:Acyl Coenzyme A; D004952:Esters; D014812:Vitamin K; C055511:4-(2'-carboxyphenyl)-4-oxobutyryl-coenzyme A ester