Abstract
The coenzyme A (CoA) and adenosine 5'-triphosphate-dependent conversion of o-succinylbenzoic acid (4-[2'-carboxyphenyl]-4-oxobutyric acid) to 1,4-dihydroxy-2-naphthoic acids is an important step in menaquinone (vitamin K2) biosynthesis. Cell-free extracts catalyzing this conversion, obtained from Mycobacterium phlei, were separated into three protein fractions by treatment with protamine sulfate. The second fraction (fraction B) and the supernatant (fraction S) alone did not catalyze dihydroxynaphthoate formation, but did so in combination. All of the results were consistent with the formation of an unstable intermediate, likely an o-succinylbenzoyl-CoA compound, by the action of fraction S. Adenosine 5'-triphosphate was required in this reaction and adenosine 5'-monophosphate was formed. This enzyme activity was termed o-succinylbenzoyl-CoA synthetase: the enzyme showed a marked stability to 0.1 N hydrochloric acid. The presumed o-succinylbenzoyl-CoA derivate was rather unstable; under a variety of conditions, it was converted to a spirodilactone form of o-succinylbenzoate. Fraction B contained an enzyme, termed naphthoate synthase, which converted the o-succinylbenzoyl-CoA derivative to 1,4-dihydroxy-2-naphthoate.
Full text
PDF
Selected References
These references are in PubMed. This may not be the complete list of references from this article.
- Bradford M. M. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal Biochem. 1976 May 7;72:248–254. doi: 10.1016/0003-2697(76)90527-3. [DOI] [PubMed] [Google Scholar]
- Dansette P., Azerad R. A new intermediate in naphthoquinone and menaquinone biosynthesis. Biochem Biophys Res Commun. 1970 Sep 10;40(5):1090–1095. doi: 10.1016/0006-291x(70)90906-x. [DOI] [PubMed] [Google Scholar]
- Hutson K. G., Threlfall D. R. Formation of spirodilactone of 4-(2'-carboxyphenyl)-4,4-dihydroxybutyrate from 2-succinylbenzoate in cell-free extracts of Micrococcus luteus. Biochim Biophys Acta. 1978 Jul 25;530(1):1–8. doi: 10.1016/0005-2760(78)90120-0. [DOI] [PubMed] [Google Scholar]
- McGovern E. P., Bentley R. Isolation and properties of naphthoate synthetase from Mycobacterium phlei. Arch Biochem Biophys. 1978 May;188(1):56–63. doi: 10.1016/0003-9861(78)90355-7. [DOI] [PubMed] [Google Scholar]