Structural elucidation of phosphoglycolipids from strains of the bacterial thermophiles Thermus and Meiothermus

Yu-Liang Yang^*, Feng-Ling Yang^*, Shu-Chuan Jao^*, Mao-Yen Chen^*^,, San-San Tsay, Wei Zou and Shih-Hsiung Wu^*^,**^,1

^* Institute of Biological Chemistry, Academia Sinica, Taipei 115, Taiwan
Department of Life Science and Institute of Plant Biology, National Taiwan University, Taipei 106, Taiwan
Institute for Biological Sciences, National Research Council of Canada, Ottawa, Ontario, Canada
^** Institute of Biochemical Sciences, National Taiwan University, Taipei 106, Taiwan

Published, JLR Papers in Press, May 4, 2006.

^¹ To whom correspondence should be addressed. e-mail: shwu{at}gate.sinica.edu.tw

The structures of two major phosphoglycolipids from the thermophilicbacteria Thermus oshimai NTU-063, Thermus thermophilus NTU-077,Meiothermus ruber NTU-124, and Meiothermus taiwanensis NTU-220were determined using spectroscopic and chemical analyses tobe 2'-O-(1,2-diacyl-sn-glycero-3-phospho) -3'-O-( ${alpha}$ -N-acetyl-glucosaminyl)-N-glyceroylalkylamine [PGL1 (1)] and the novel structure 2'-O-(2-acylalkyldio-1-O-phospho)-3'-O-( ${alpha}$ -N-acetylglucosaminyl)-N-glyceroylalkylamine [PGL2 (2)]. PGL2 (2) is the first phosphoglycolipididentified with a 2-acylalkyldio-1-O-phosphate moiety. The fattyacids of the phosphoglycolipids are mainly iso-C_15:0, -C_16:0,and -C_17:0 and anteiso-C_15:0 and -C_17:0. The ratios of PGL2(2) to PGL1 (1) are significantly altered when grown at differenttemperatures for three strains, T. thermophilus NTU-077, M.ruber NTU-124, and M. taiwanensis NTU-220, but not for T. oshimaiNTU-063. Accordingly, the ratios of iso- to anteiso-branchedfatty acids increase when grown at the higher temperature.

Abbreviations: CE-MS, capillary electrophoresis-mass spectroscopy; DQF-COSY, double quantum filtered-correlation spectroscopy; FAME, fatty acid methyl ester; gHMQC, gradient heteronuclear multiple quantum coherence; HMBC, heteronuclear multiple bond coherence; HPAEC-PAD, high-performance anion-exchange chromatography with pulsed amperometric detection; MALDI, matrix-assisted laser desorption ionization; PGL1, 2'-O-(1,2-diacyl-sn-glycero-3-phospho)-3'-O-( ${alpha}$ -N-acetyl-glucosaminyl)-N-glyceroyl alkylamine; PGL2, 2'-O-(2-acylalkyldio-1-O-phospho)-3'-O-( ${alpha}$ -N-acetylglucosaminyl)-N-glyceroyl alkylamine; ROESY, rotational frame nuclear Overhauser effect spectroscopy; TOCSY, total correlation spectroscopy; 2D, two-dimensional

Supplementary key words nuclear magnetic resonance spectroscopy • matrix-assisted laser desorption ionization mass spectroscopy • capillary electrophoresis-mass spectroscopy • tandem mass spectrometry • Thermus oshimai NTU-063 • Thermus thermophilus NTU-077 • Meiothermus ruber NTU-124 • Meiothermus taiwanensis NTU-220

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