Novel Polyoxyethylene-Containing Glycolipids Are Synthesized in Corynebacterium matruchotii and Mycobacterium smegmatis Cultured in the Presence of Tween 80.
Novel Polyoxyethylene-Containing Glycolipids Are Synthesized in Corynebacterium matruchotii and Mycobacterium smegmatis Cultured in the Presence of Tween 80.
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DOI：
10.1155/2011/676535
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发表时间：
2011
影响因子：
5.3
通讯作者：
Takayama K
中科院分区：
文献类型：
--
作者：
Wang C;Mahrous EA;Lee RE;Vestling MM;Takayama K
在分枝杆菌培养物中加入聚氧乙烯脱水山梨糖醇单油酸酯（吐温80）会极大地影响细胞的渗透性和对抗生素的敏感性，但关于其潜在机制知之甚少。在这里，我们表明，棒状杆菌matruchotii（分枝杆菌的替代品）转化吐温80的聚氧乙烯酸，然后用于形成新的系列-2A和系列-2B糖脂的结构系列。还合成了次要系列-3糖脂。聚氧乙烯酸取代了细胞壁中的corynomycolic酸。相应地，海藻糖双谷菌酸酯含量降低。采用MALDI质谱、MS-MS、1H-NMR和13 C-NMR对系列-2糖脂进行表征。2A系列糖脂为海藻糖6-C36：2-corynomycolate-6′-聚氧乙烯酯，2B系列糖脂为海藻糖6-C36：2-corynomycolate-6′-含呋喃环的聚氧乙烯酯。在吐温80存在下生长的耻垢分枝杆菌也合成系列-2型糖脂。棒状杆菌和分枝杆菌中这些新型糖脂的合成应导致细胞壁渗透性和药物敏感性的总体变化。
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, 1H-NMR, and 13C-NMR were used to characterize the series-2 glycolipids. Series-2A glycolipid is trehalose 6-C36:2-corynomycolate-6′-polyoxyethylenate and series-2B glycolipid is trehalose 6-C36:2-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.