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Volume 272, Number 42, Issue of October 17, 1997 pp. 26262-26270
©1997 by The American Society for Biochemistry and Molecular Biology, Inc.

Primary Structure of a New Phosphocholine-containing Glycoglycerolipid of Mycoplasma fermentans

(Received for publication, February 25, 1997, and in revised form, June 4, 1997)

Ulrich Zähringer , Frauke Wagner , Ernst Th. Rietschel , Gil Ben-Menachem ^¶ , Joseph Deutsch and Shlomo Rottem ^¶

From the  Research Center Borstel, Center for Medicine and Biosciences, Parkallee 22, D-23845 Borstel, Federal Republic of Germany, the ^¶ Department of Membrane and Ultrastructure Research, The Hebrew University-Hadassah Medical School, and the  Department of Pharmaceutical Chemistry, School of Pharmacy, The Hebrew University, Jerusalem 91010, Israel

The chemical structure of a novel phosphocholine-containing glycoglycerolipid, the major polar lipid in the cell membrane of Mycoplasma fermentans PG18, was investigated by chemical analyses, gas-liquid chromatography-mass spectrometry, matrix-assisted laser desorption/ionization time-of-flight (MALDI-TOF) mass spectrometry, as well as one- and two-dimensional homo- and heteronuclear NMR spectroscopy and identified as 6-O-(3"-phosphocholine-2"-amino-1"-phospho-1",3"-propanediol)--D-glucopyranosyl-(13)-1,2-diacyl-glycerol (MfGL-II). Palmitate (16:0) and stearate (18:0), in a 3.6:1 molar ratio, constitute the major fatty acids present. MALDI-TOF mass spectrometry revealed two major pseudomolecular ions at m/z 1049.5 [M^I + H]⁺ and 1077.3 [M^II + H]⁺ representing a dipalmitoyl as the major component and a palmitoyl-stearoyl structure as a minor component. This is the first report of 2-amino-1,3-propanediol-1,3-bisphosphate present in a natural product. This glycoglycerolipid is the second phosphocholine-containing glycoglycerolipid found in M. fermentans.

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