HOME HELP FEEDBACK SUBSCRIPTIONS ARCHIVE SEARCH TABLE OF CONTENTS		QUICK SEARCH:   [advanced] Author: Keyword(s): Year:  Vol:  Page:

This Article Full Text Full Text (PDF) Alert me when this article is cited Alert me if a correction is posted Citation Map Services Email this article to a friend Similar articles in this journal Similar articles in PubMed Alert me to new issues of the journal Download to citation manager Citing Articles Citing Articles via HighWire Citing Articles via Google Scholar Google Scholar Articles by Moormann, M. Articles by Altendorf, K. Search for Related Content PubMed PubMed Citation Articles by Moormann, M. Articles by Altendorf, K. Social Bookmarking                      What's this?

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

---

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.

CiteULike    Complore    Connotea    Del.icio.us    Digg    Reddit    Technorati    What's this?

This article has been cited by other articles:

				G. Etienne, F. Laval, C. Villeneuve, P. Dinadayala, A. Abouwarda, D. Zerbib, A. Galamba, and M. Daffe The cell envelope structure and properties of Mycobacterium smegmatis mc2155: is there a clue for the unique transformability of the strain? Microbiology, June 1, 2005; 151(6): 2075 - 2086. [Abstract] [Full Text] [PDF]

				M. Arenskotter, D. Broker, and A. Steinbuchel Biology of the Metabolically Diverse Genus Gordonia Appl. Envir. Microbiol., June 1, 2004; 70(6): 3195 - 3204. [Full Text] [PDF]

				G. Etienne, C. Villeneuve, H. Billman-Jacobe, C. Astarie-Dequeker, M.-A. Dupont, and M. Daffe The impact of the absence of glycopeptidolipids on the ultrastructure, cell surface and cell wall properties, and phagocytosis of Mycobacterium smegmatis Microbiology, October 1, 2002; 148(10): 3089 - 3100. [Abstract] [Full Text] [PDF]