Novel Polyoxyethylene-Containing Glycolipids Are Synthesized in Corynebacterium matruchotii and Mycobacterium smegmatis Cultured in the Presence of Tween 80

Figure 3

Predicted products of degradation of Tween 80 by C. matruchotii. Structure A is polyoxyethylenic acid derived from the furan ring of Tween 80 (http://www.sigma-aldrich.com/) and structure B is the furan ring-associated polyoxyethylenic acid. Structures C and D are further degradation products of B. The terminal hydroxyl group is thought to be oxidized to the carboxyl group and all of these products are used by the bacteria to synthesize series-2A and -2B glycolipids. Alternative to structure B, the carboxylic acid group could be on the other polyoxyethylenate unit. The proposed structures of series-2A and -2B glycolipids are shown in upper right and lower right panels, respectively.