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- W2046242562 abstract "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,<mml:math xmlns:mml=http://www.w3.org/1998/Math/MathML><mml:mn>1</mml:mn><mml:mtext>H</mml:mtext></mml:math>-NMR, and<mml:math xmlns:mml=http://www.w3.org/1998/Math/MathML><mml:mn>13</mml:mn><mml:mtext>C</mml:mtext></mml:math>-NMR were used to characterize the series-2 glycolipids. Series-2A glycolipid is trehalose 6-<mml:math xmlns:mml=http://www.w3.org/1998/Math/MathML><mml:msub><mml:mtext>C</mml:mtext><mml:mrow><mml:mn>36</mml:mn><mml:mo>:</mml:mo><mml:mn>2</mml:mn></mml:mrow></mml:msub></mml:math>-corynomycolate-<mml:math xmlns:mml=http://www.w3.org/1998/Math/MathML><mml:msup><mml:mn>6</mml:mn><mml:mo>′</mml:mo></mml:msup></mml:math>-polyoxyethylenate and series-2B glycolipid is trehalose 6-<mml:math xmlns:mml=http://www.w3.org/1998/Math/MathML><mml:msub><mml:mtext>C</mml:mtext><mml:mrow><mml:mn>36</mml:mn><mml:mo>:</mml:mo><mml:mn>2</mml:mn></mml:mrow></mml:msub></mml:math>-corynomycolate-<mml:math xmlns:mml=http://www.w3.org/1998/Math/MathML><mml:msup><mml:mn>6</mml:mn><mml:mo>′</mml:mo></mml:msup></mml:math>-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." @default.
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- W2046242562 date "2011-01-01" @default.
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- W2046242562 title "Novel Polyoxyethylene-Containing Glycolipids Are Synthesized in<i>Corynebacterium matruchotii</i>and<i>Mycobacterium smegmatis</i>Cultured in the Presence of Tween 80" @default.
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- W2046242562 doi "https://doi.org/10.1155/2011/676535" @default.
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