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Infection and Immunity, September 2004, p. 5340-5348, Vol. 72, No. 9
0019-9567/04/$08.00+0     DOI: 10.1128/IAI.72.9.5340-5348.2004
Copyright © 2004, American Society for Microbiology. All Rights Reserved.

Novel Modification of Lipid A of Francisella tularensis

Nancy J. Phillips,1 Birgit Schilling,2 Molly K. McLendon,3 Michael A. Apicella,3 and Bradford W. Gibson1,2*

Department of Pharmaceutical Chemistry, University of California, San Francisco, San Francisco,1 The Buck Institute for Age Research, Novato, California,2 Department of Microbiology, The University of Iowa, Iowa City, Iowa3

Received 15 January 2004/ Returned for modification 3 March 2004/ Accepted 2 June 2004

We have investigated the lipid A of Francisella tularensis subsp. holarctica strain 1547-57, a type B strain, by using matrix-assisted laser desorption ionization-time-of-flight mass spectrometry, nanoelectrospray quadrupole ion-trap mass spectrometry, and chemical methods. In accordance with the previously published structures of the lipid A from F. tularensis live vaccine strain (LVS) (ATCC 29684) (E. Vinogradov et al., Eur. J. Biochem. 269:6112-6118, 2002), all of the major lipid A forms from strain 1547-57 were tetraacylated. As in the LVS strain, the major fatty acids detected in the F. tularensis 1547-57 lipid A sample included 3-hydroxyoctadecanoic acid, 3-hydroxyhexadecanoic acid, hexadecanoic acid, and tetradecanoic acid. However, several of the lipid A components present in strain 1547-57 were of higher molecular weight than the previously published structures. A major component with an Mr of 1,666 was found to contain three C18:0(3-OH) fatty acids, one C16:0 fatty acid, one phosphate group, and one 161-Da moiety. This 161-Da moiety could be removed from the lipid A by treatment with aqueous hydrofluoric acid and was identified as galactosamine following peracetylation and analysis by gas chromatography-mass spectrometry. Detailed investigations of the Mr-1,666 species by ion-trap mass spectrometry with multiple stages of fragmentation suggested that the galactosamine-1-phosphate was linked to the reducing terminus of the lipid A. Similar to the modification of lipid A with arabinosamine, lipopolysaccharide species from F. tularensis containing a phosphate-linked galactosamine could potentially influence its intracellular survival by conferring resistance to antimicrobial peptides.

* Corresponding author. Mailing address: The Buck Institute for Age Research, Novato, CA 94945. Phone: (415) 209-2032. Fax: (415) 209-2231. E-mail: bgibson{at}buckinstitute.org.

Editor: J. N. Weiser

Infection and Immunity, September 2004, p. 5340-5348, Vol. 72, No. 9
0019-9567/04/$08.00+0     DOI: 10.1128/IAI.72.9.5340-5348.2004
Copyright © 2004, American Society for Microbiology. All Rights Reserved.



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