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J. Lipid Res.
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Originally published In Press as doi:10.1194/jlr.M800549-JLR200 on December 18, 2008

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Journal of Lipid Research, Vol. 50, 1589-1599, August 2009
Copyright © 2009 by American Society for Biochemistry and Molecular Biology

Identification of phosphatidylserylglutamate: a novel minor lipid in Escherichia coli

Teresa A. Garrett1,*, Christian R. H. Raetz{dagger}, Travis Richardson2,{dagger}, Reza Kordestani{dagger}, Jennifer D. Son* and Rebecca L. Rose*

* Department of Chemistry, Vassar College, Poughkeepsie, NY 12604
{dagger} Department of Biochemistry, Duke University Medical Center, Durham, NC 27710

1 To whom correspondence should be addressed. e-mail: tegarrett{at}vassar.edu

Advances in mass spectrometry have facilitated the identification of novel lipid structures. In this work, we fractionated the lipids of Escherichia coli B and analyzed the fractions using negative-ion electrospray ionization mass spectrometry to reveal unknown lipid structures. Analysis of a fraction eluting with high salt from DEAE cellulose revealed a series of ions not corresponding to any of the known lipids of E. coli. The ions, with m/z 861.5, 875.5, 887.5, 889.5, and 915.5, were analyzed using collision-induced dissociation mass spectrometry (MS/MS) and yielded related fragmentation patterns consistent with a novel diacylated glycerophospholipid. Product ions arising by neutral loss of 216 mass units were observed with all of the unknowns. A corresponding negative product ion was also observed at m/z 215.0. Additional ions at m/z 197.0, 171.0, 146.0, and 128.0 were used to propose the novel structure phosphatidylserylglutamate (PSE). The hypothesized structure was confirmed by comparison with the MS/MS spectrum of a synthetic standard. Normal phase liquid chromatography-mass spectrometry analysis further showed that the endogenous PSE and synthetic PSE eluted with the same retention times. PSE was also observed in the equivalent anion exchange fractions of total lipids extracted from the wild-type E. coli K-12 strain MG1655.

Supplementary key words mass spectrometry • lipid structure determination • electrospray ionization

Abbreviations: CL, cardiolipin; ESI-MS, electrospray ionization-mass spectrometry; HPTLC, high-performance thin-layer chromatography; IDA, information-dependent acquisition; LB, Luria broth; LC-MS, liquid chromatography-mass spectrometry; MS/MS, collision-induced dissociation mass spectrometry; PA, phosphatidic acid; PE, phosphatidylethanolamine; PG, phosphatidylglycerol; PG-P, phosphatidylglycerol phosphate; PSE, phosphatidylserylglutamate


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