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Volume 272, Number 16, Issue of April 18, 1997 pp. 10729-10738
©1997 by The American Society for Biochemistry and Molecular Biology, Inc.

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A New Glycosylated Lipopeptide Incorporated into the Cell Wall of a Smooth Variant of Gordona hydrophobica

(Received for publication, November 25, 1996, and in revised form, January 14, 1997)

Michael Moormann , Ulrich Zähringer ^§ , Hermann Moll ^§ , Raimund Kaufmann ^¶ , Roland Schmid and Karlheinz Altendorf

From the  Abteilung Mikrobiologie, Universität Osnabrück, D-49069 Osnabrück, the ^§ Division of Immunochemistry, Forschungszentrum Borstel, Parkallee 22, D-23845 Borstel, and the ^¶ Institut für Lasermedizin und Biologisch Medizinisches Forschungszentrum (BMFZ), Heinrich-Heine-Universität, Postfach 101007, D-40001 Düsseldorf, Federal Republic of Germany

A cell wall component of a smooth variant of Gordona hydrophobica 1775/15 was isolated and purified, and its structure was determined by various chemical methods, including chemical synthesis of part structures, Edman degradation, gas chromatography/mass spectrometry analysis, matrix-assisted laser desorption ionization-post-source decay (MALDI-PSD) tandem mass spectrometry, and ¹H and ¹³C NMR using one- and two-dimensional, homo- and heteronuclear correlated spectroscopy. The cell wall component was found to be a (mono-) glycosylated peptidolipid (GPL) consisting of a tridecapeptide interlinked by a -hydroxylated fatty acid (3-hydroxyeicosanoic acid, 20:0 (3-OH)) to form a cyclic lactone ring structure. The main fraction of GPL, for which we propose the name gordonin, was identified as 3-hydroxyeicosanoyl-L-seryl-L-phenylalanyl-L-seryl-L-seryl-D-alanyl-L-(O--D-glucopyranosyl)-threonyl-glycyl-D-leucyl-L-valyl-L-seryl-L-phenylalanyl-glycyl-L-valyl lactone. The other GPLs constitute structural variations within the nature of the -hydroxylated fatty acid (20:0(3-OH) versus 22:1(3-OH)) in a ratio of about 1:0.9 as well as within one amino acid (D-Leu versus L-Phe) in about 30%. Sequence information was obtained in part by Edman degradation as well as gas chromatography/mass spectrometry analysis of di- and tripeptide fragments. However, the complete amino acid sequence could only be established by MALDI-PSD from the linear molecule, i.e. after ring opening of the lactone.

In contrast, rough variants of G. hydrophobica 1775/15 lack these peptidolipids or synthesize them to a much lesser extent indicating that gordonin contributes significantly to the physicochemical character of the cell surface.

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