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Glycobiology Advance Access originally published online on April 24, 2006
Glycobiology 2006 16(8):766-775; doi:10.1093/glycob/cwj120
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© The Author 2006. Published by Oxford University Press. All rights reserved. For permissions, please e-mail: journals.permissions@oxfordjournals.org

The structures of glycolipids isolated from the highly thermophilic bacterium Thermus thermophilus Samu-SA1

Serena Leone2,3, Antonio Molinaro1,2, Buko Lindner4, Ida Romano5, Barbara Nicolaus5, Michelangelo Parrilli2, Rosa Lanzetta2 and Otto Holst3

2 Dipartimento di Chimica Organica e Biochimica, Università degli Studi di Napoli Federico II, Via Cintia 4, I-80126 Napoli, Italy; 3 Division of Structural Biochemistry, Research Center Borstel and 4 Department of Immunochemistry and Biochemical Microbiology, Research Center Borstel, Leibniz Center for Medicine and Biosciences, Parkallee 10, D-23845 Borstel, Germany; and 5 Istituto di Chimica Biomolecolare (ICB-CNR), via Campi Flegrei 34, 80078 Pozzuoli, Napoli, Italy

1 To whom correspondence should be addressed; e-mail: molinaro{at}unina.it

Received on March 28, 2006; revised on April 20, 2006; accepted on April 21, 2006

Thermophiles constitute a class of microorganisms able to grow at extremely elevated temperatures. Some of these species are classified as Gram-negative bacteria, because of the presence of an outer membrane in the cell envelope, which is located on the top of a thick murein layer. Unlike typical Gram-negative bacteria, the outer membranes of Thermus species are not composed of lipopolysaccharides but of peculiar glycolipids (GL), whose structures seem to be strictly involved in the adaptation to high temperatures. In this work, the complete structures of the major GL components from the cell envelope of the thermophilic bacterium Thermus thermophilus Samu-SA1 are presented. Protocols conventionally adopted for Gram-negative bacteria were used, and, for the first time, GL from Thermus were analyzed in their native form. Two GL and one phosphoglycolipid (PGL) were detected and characterized. The two GL, analyzed by nuclear magnetic resonance (NMR) spectroscopy and electrospray ionization Fourier transform ion cyclotron resonance (ESI FT-ICR) mass spectrometry, possessed the same tetrasaccharide structure linked to a glycerol unit or, alternatively, to a long-chain diol. Moreover, a PGL from Thermus was characterized for the first time, in which N-glyceroyl-heptadecaneamine was present. These molecules are chemically related to other GL from thermophile bacteria, in which they play a crucial role in the adaptation of cell membranes to heat.

Key words: ESI FT-MS / glycolipid / long-chain diol / NMR / Thermus thermophilus


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