Trehalose-6-corynomycolate

TABLE 1 Characteristic Data on the Microbial Production of Rhamnose Lipids (RLs), Trehalose Corynomycolates (TL-Cs), and Anionic Trehalose Lipids (TLs), Respectively... 

Aqueous solutions of nonionic trehalose corynomycolates and of anionic trehalose tetraesters indicated surface tension values of 32/36 mN/m (CMC, 5 mg/L) and of 26 mN/m (CMC, 15 mg/L), respectively. Studies on potential applications in environmental remediation, oil industry, cosmetics, and use in activated sludge plants have been summarized by Lang and Philp [25]. Recently, the enhanced oil desorption from mineral and organic materials using biosurfactant complexes produced by Rhodococcus species, particularly R. ruber, was observed [32]. 

Here, too, 6-mono-, 6,6 -di-, and 2,6,6 -tri-esters of trehalose have been obtained. More recently, Diara and Pudles have prepared the 6,6 -dicorynomycolate of trehalose, using natural corynomycolic acid (19) isolated from Corynebacterium diphtheriae. ... 

The purification procedure of 6,6 -esters of OMf-trehalose from Coryne-bacterium diphtheria has been modified and the products were analysed by m.s. of the permethylated derivative.The constituent fatty acids have been extensively examined and the detailed structure of the major acids have been confirmed by a variety of techniques. Novel glycolipids in the cord factor fraction from C. diphtheria were a 6,6 -bis(3-oxo-acyl)-o a -D-trehalose and a 6, 6 -mixed ester of aa-trehalose with the 3-oxo-acyl group and a corynomycolic acid. The metabolic implications of these structural studies suggest that condensation of the common fatty acids by a Claisen-like process via the oxo-ester pathway may not be the only pathway for the synthesis of the cord factors. 

Biosynthesis studies revealed that the lipid component as well as the trehalose unit were first synthesized independently of each other and subsequently were linked together. As for the above-mentioned strains, an exemplary synopsis on biosynthesis, production, and potential applications was presented for surface-active lipids of rhodococci [25]. Only recently using Corynebacterium matruchotii the following facts were clarified (1) Treha-lose-6-phosphate, but not trehalose, stimulated corynomycolate synthesis... 

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