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The addition of polyoxyethylene sorbitan monooleate (Tween 80) to a culture of mycobacteria greatly influences cell permeability and sensitivity to antibiotics but very little is known regarding the underlying mechanism. Here we show that  Corynebacterium matruchotii  (surrogate of mycobacteria) converts Tween 80 to a structural series of polyoxyethylenic acids which are then used to form novel series-2A and series-2B glycolipids. Minor series-3 glycolipids were also synthesized. The polyoxyethylenic acids replaced corynomycolic acids in the cell wall. Correspondingly the trehalose dicorynomycolate content was reduced. MALDI mass spectrometry, MS-MS,  1 H-NMR, and  13 C-NMR were used to characterize the series-2 glycolipids. Series-2A glycolipid is trehalose 6-C 36:2 -corynomycolate-6′-polyoxyethylenate and series-2B glycolipid is trehalose 6-C 36:2 -corynomycolate-6′-furan ring-containing polyoxyethylenate.  Mycobacterium smegmatis  grown in the presence of Tween 80 also synthesizes series-2 type glycolipids. The synthesis of these novel glycolipids in corynebacteria and mycobacteria should result in gross changes in the cell wall permeability and drug sensitivity.

journal of lipids

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

Novel Polyoxyethylene-Containing Glycolipids Are Synthesized inCorynebacterium matruchotiiandMycobacterium smegmatisCultured in the Presence of Tween 80