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

Wang C, Mahrous EA, Lee RE, Vestling MM, Takayama K - J Lipids (2010)

Bottom Line: 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.

View Article: PubMed Central - PubMed

Affiliation: Mycobacteriology Research Laboratory, William S. Middleton Memorial Veterans Hospital, Madison, WI 53705, USA.

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, (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.

No MeSH data available.


Related in: MedlinePlus

MS-MS spectrum of the lifted MNa+ peak at m/z 1331.  Inset shows the structure and fragmentation pattern of this glycolipid from series-2B mass spectrum (Figure S1).
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fig5: MS-MS spectrum of the lifted MNa+ peak at m/z 1331. Inset shows the structure and fragmentation pattern of this glycolipid from series-2B mass spectrum (Figure S1).

Mentions: Figure 5 shows the MS-MS spectrum of the lifted MNa+ peak at 1331, the proposed structure and the pattern of fragmentation. It showed the molecular ion MNa+ peak at m/z 1331. It also showed MNa+-30 at m/z 1301 and MNa+-45 at m/z 1286. This is consistent with the given structure. The fragmentation of the m/z 1331 peak was not as extensive as that of the m/z 1111 peak.


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

Wang C, Mahrous EA, Lee RE, Vestling MM, Takayama K - J Lipids (2010)

MS-MS spectrum of the lifted MNa+ peak at m/z 1331.  Inset shows the structure and fragmentation pattern of this glycolipid from series-2B mass spectrum (Figure S1).
© Copyright Policy - open-access
Related In: Results  -  Collection

Show All Figures
getmorefigures.php?uid=PMC3066834&req=5

fig5: MS-MS spectrum of the lifted MNa+ peak at m/z 1331. Inset shows the structure and fragmentation pattern of this glycolipid from series-2B mass spectrum (Figure S1).
Mentions: Figure 5 shows the MS-MS spectrum of the lifted MNa+ peak at 1331, the proposed structure and the pattern of fragmentation. It showed the molecular ion MNa+ peak at m/z 1331. It also showed MNa+-30 at m/z 1301 and MNa+-45 at m/z 1286. This is consistent with the given structure. The fragmentation of the m/z 1331 peak was not as extensive as that of the m/z 1111 peak.

Bottom Line: 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.

View Article: PubMed Central - PubMed

Affiliation: Mycobacteriology Research Laboratory, William S. Middleton Memorial Veterans Hospital, Madison, WI 53705, USA.

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, (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.

No MeSH data available.


Related in: MedlinePlus