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Journal of Lipids
Volume 2011 (2011), Article ID 676535, 12 pages
Research Article

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

1Mycobacteriology Research Laboratory, William S. Middleton Memorial Veterans Hospital, Madison, WI 53705, USA
2Chemical Biology & Therapeutics, St. Jude Children's Research Hospital, Memphis, TN 38105, USA
3Department of Chemistry, University of Wisconsin, Madison, WI 53706, USA
4Department of Bacteriology, University of Wisconsin, Madison, WI 53706, USA

Received 16 March 2010; Accepted 21 April 2010

Academic Editor: Sampath Parthasarathy

Copyright © 2011 Cindy Wang et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.


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, -NMR, and -NMR were used to characterize the series-2 glycolipids. Series-2A glycolipid is trehalose 6- -corynomycolate- -polyoxyethylenate and series-2B glycolipid is trehalose 6- -corynomycolate- -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.