Corynomycolic acid

R)-liINAP-RuBr2 can be successfully applied to the enantioselective hydrogenation of /i-kelo esters in the synthesis of (+)-(2R,3 W)-corynomycolic acid 115. ( S )-MeO-BIPHEP-RuBr2 was used in a similar manner in the synthesis of (R)-fluoxetine (116, Prozac ) and (S)-duloxetine (117).648... 

Fatty acid 2-Hydroxy-octadecanoic acid Corynomycolic acid... 

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. 

The skeleton consists of a branched polymer of D-arabinose and D-galactose in a 5 2 ratio where about every tenth arabinose contains a mycolic acid esterified to the 5 -hydroxyl. These mycolic acids are 60-90 carbon fatty acids which are 2-branched and 3-hydroxylated. They may also contain cyclopropane rings, methyl branches and methoxy groups. In Nocardia similar arabinogalactan mycolates are present, known as nocardomycolic acids (40-60 carbons with a Ci4 or Ci6branch). In Corynebacterium spp., corynomycolic acids (28-40 carbons with a C14 branch) are found (Minnikin, 1982). 

There are alkyne fatty acids such as crepenynic acid (104 C18) and fatty acids that contain branches such as corynomycolic acid (105 C32), found in Corynebactrium diphtheriae, or tuberculostearic acid (106 C19), which is found in Mycobacterium tuberculosis. These latter organisms are responsible for diphtheria and tuberculosis, respectively. 

Fujii, T., Yuasa, R. and Kawase, T. (1999) Biodetergent. Part 4. Monolayers of corynomycolic acids at the air-water interface. Colloid Polym. ScL, 277, 334-339. 

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