The chemistry of some native constituents of the purified wax of Mycobacterium tuberculosis
Journal of Biological Chemistry
Purified wax," as isolated by Anderson, is a complex lipide extracted from cultures of acid-fast bacilli with chloroform. It is characterized by its insolubility in methanol (1). Anderson investigated its composition by chemical identification of the fragments after hydrolytic degradation. The results indicated that the purified wax was not chemically homogeneous, and the question of how the hydrolytic fragments were originally combined has not been answered. Progress toward the isolation of
... the isolation of the native constituents of the purified wax was made by Asselmeau (2). Extracting the purified wax with boiling acetone, he obtained a soluble portion termed "Wax C" and an insoluble residue, the "Wax D" fraction. Wax C was characterized by its low melting point and the absence of nitrogen and high molecular carbohydrate components, and Wax D consisted chiefly of high molecular lipopolysaccharides containing small amounts of nitrogen and phosphorus (2,3). Introducing the technique of chromatographic partitioning, Asselineau was able to isolate from Wax C two components in a pure state, which he identitled as mycolic acid and an ester of phthiocerol. Later, Philpot and Wells (4) identified the acid part of this ester as mycocerosic acid. A continuation and extension of the work on composition and chemistry of the native constituents of Wax C are reported in the present paper. An improved method of solvent partitioning of the purified wax resulted in a better defined separation of Wax C and Wax D. Several new compounds were isolated from the Wax C of various virulent strains of Mycobuctium tuberculosis, among these a triglyceride of a long chain fatty acid (C" to C26) and a monoglyceride of mycolic acid.