Characterization of Ornithine and Glutamine Lipids Extracted from Cell Membranes of Rhodobacter sphaeroides

Journal of the American Society for Mass Spectrometry

Volumn 20, Issue 2, 2009, Pages 198-212

  Zhang, Xi ^a,b   Ferguson Miller, Shelagh M ^b   Reid, Gavin E ^a,b  

^a MICHIGAN STATE UNIVERSITY   (United States)

^b Michigan State University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE LINKED; ANALOGOUS STRUCTURES; CELLULAR EXTRACTS; FATTY ACYL CHAINS; FRAGMENTATION BEHAVIORS; FRAGMENTATION PATHWAYS; FRAGMENTATION REACTIONS; GLYCEROPHOSPHOCHOLINE; HEAD GROUPS; HYDROGEN/DEUTERIUM EXCHANGES; LINEAR QUADRUPOLE ION TRAPS; NEGATIVE ION MODES; POSITIVE ION MODES; POSITIVELY CHARGED; PRECURSOR IONS; PROTONATED; QUANTITATIVE ANALYSES; RHODOBACTER SPHAEROIDES; STRUCTURAL CHARACTERIZATIONS; TANDEM MASS SPECTROMETRIES;

AMIDES; AMINO ACIDS; CELL MEMBRANES; CHEMICAL REACTIONS; CYTOLOGY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ION EXCHANGE; LIPIDS; MASS SPECTROMETRY; MODEL STRUCTURES; NEGATIVE IONS;

IONS;

CELL MEMBRANE; GLUTAMINE; GLYCERYLPHOSPHORYLCHOLINE; LIPIDS; ORNITHINE; RHODOBACTER SPHAEROIDES; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; TANDEM MASS SPECTROMETRY;

RHODOBACTER SPHAEROIDES;

EID: 58249084018     PISSN: 10440305     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jasms.2008.08.017     Document Type: Article

References (38)

1. Gorchein A. Distribution and Metabolism of Ornithine in Rhodopseudomonas sphaeroides. Proc. Roy. Soc. Ser. B 170 (1968) 265-278
2. Shively J.M., and Knoche H.W. Isolation of an Ornithine-Containing Lipid from Thiobacillus thiooxidans. J. Bacteriol 98 (1969) 829-830
3. Knoche H.W., and Shively J.M. The Structure of an Ornithine-Containing Lipid from Thiobacillus thiooxidans. J. Biol. Chem 247 (1972) 170-178
4. Lopez-Lara I.M., Sohlenkamp C., and Geiger O. Membrane Lipids in Plant-Associated Bacteria: Their Biosyntheses and Possible Functions. Mol. Plant-Microbe Interact 16 (2003) 567-579
5. Minnikin D.E., and Abdolrahimzadeh H. Replacement of Phosphatidylethanolamine and Acidic Phospholipids by an Ornithine-Amide Lipid and a Minor Phosphorus-Free Lipid in Pseudomonas fluorescens NCMB 129. FEBS (Fed. Eur. Biochem. Soc.) Lett 43 (1974) 257-260
6. Benning C., Huang Z.-H., and Gage D.A. Accumulation of a Novel Glycolipid and a Betaine Lipid in Cells of Rhodobacter sphaeroides grown under phosphate limitation. Arch. Biochem. Biophys 317 (1995) 103-111
7. Lopez-Lara I.M., Gao J.-L., Soto M.J., Solares-Perez A., Weissenmayer B., Sohlenkamp C., Verroios G.P., Thomas-Oates J., and Geiger O. Phosphorus-Free Membrane Lipids of Sinorhizobium meliloti Are Not Required for the Symbiosis with Alfalfa but Contribute to Increased Cell Yields Under Phosphorus-Limiting Conditions of Growth. Mol. Plant-Microbe Interact 18 (2005) 973-982
8. Weissenmayer B., Gao J.-L., Lopez-Lara I.M., and Geiger O. Identification of a Gene Required for the Biosynthesis of Ornithine-Derived Lipids. Mol. Microbiol 45 (2002) 721-733
9. Taylor C.J., Anderson A.J., and Wilkinson S.G. Phenotypic Variation of Lipid Composition in Burkholderia cepacia: A Response to Increased Growth Temperature is a Greater Content of 2-Hydroxy Acids in Phosphatidylethanolamine and Ornithine Amide Lipid. Microbiology (Reading, U.K.) 144 (1998) 1737-1745
10. Rojas-Jimenez K., Sohlenkamp C., Geiger O., Martinez-Romero E., Werner D., and Vinuesa P. A CIC chloride Channel Homolog and Ornithine-Containing Membrane Lipids of Rhizobium tropici CIAT899 are Involved in Symbiotic Efficiency and Acid Tolerance. Mol. Plant-Microbe Interact 18 (2005) 1175-1185
11. Kawai Y., and Yano I. Ornithine-Containing Lipid of Bordetella pertussis, a new type of hemagglutinin. Eur. J. Biochem 136 (1983) 531-538
12. Kawai Y., and Akagawa K. Macrophage Activation of an Ornithine-Containing Lipid or a Serine-Containing Lipid. Infect. Immun 57 (1989) 2086-2091
13. Kawai Y., Nakagawa Y., Matuyama T., Akagawa K., Itagawa K., Fukase K., Kusumoto S., Nishijima M., and Yano I. A Typical Bacterial Ornithine-Containing Lipid N&;α-(D)-[3-(Hexadecanoyloxy)Hexadecanoyl]-Ornithine is a Strong Stimulant for Macrophages and a Useful Adjuvant. FEMS Immunol. Med. Microbiol 23 (1999) 67-73
14. Aygun-Sunar S., Mandaci S., Koch H.-G., Murray I.V.J., Goldfine H., and Daldal F. Ornithine Lipid is Required for Optimal Steady-State Amounts of c-Type cytochromes in Rhodobacter capsulatus. Mol. Microbiol 61 (2006) 418-435
15. Tamot B., Zhang X., Hiser C., Reid G.E., Ferguson-Miller S.M., and Benning C. Cytochrome c Oxidase Produced in a Cardiolipin-Deficient Mutant of Rhodobacter sphaeroides is Fully Functional and Crystallizable (2008) unpublished
16. Benning C., Beatty J.T., Prince R.C., and Somerville C.R. The Sulfolipid Sulfoquinovosyldiacylglycerol is Not Required for Photosynthetic Electron Transport in Rhodobacter sphaeroides but enhances growth under phosphate limitation. Proc. Natl. Acad. Sci. U.S.A. 90 (1993) 1561-1565
17. Arondel V., Benning C., and Somerville C.R. Isolation and Functional Expression in Escherichia coli of a gene encoding phosphatidylethanolamine methyltransferase (EC 2.1.1.17) from Rhodobacter sphaeroides. J. Biol. Chem. 268 (1993) 16002-16008
18. Yasutaka T., Yuzi Y., and Keiji K. A New Lysine-Containing Lipid Isolated from Agrobacterium tumefaciens. Agric. Biol. Chem 40 (1976) 1449-1450
19. - Production and Myeloperoxidase Release from Human Polymorphonuclear Leukocytes by the Ornithine-Containing Lipid and the Serine-Glycine-Containing Lipid of Flavobacterium. FEMS Immunol. Med. Microbiol 28 (2000) 205-209
20. Pulfer M., and Murphy R.C. Electrospray Mass Spectrometry of Phospholipids. Mass Spectrom. Rev 22 (2003) 332-364
21. Zhang X., and Reid G.E. Multistage Tandem Mass Spectrometry of Anionic Phosphatidylcholine Lipid Adducts Reveals Novel Dissociation Pathways. Int. J. Mass Spectrom 252 (2006) 242-255
22. Linscheid M., Diehl B.W.K., Oevermoehle M., Riedl I., and Heinz E. Membrane Lipids of Rhodopseudomonas viridis. Biochim. Biophys. Acta, Lipid Metab 1347 (1997) 151-163
23. Hilker D.R., Gross M.L., Knocke H.W., and Shively J.M. The Interpretation of the Mass Spectrum of an Ornithine-Containing Lipid from Thiobacillus thiooxidans. Biomed. Mass Spectrom 5 (1978) 64-71
24. Tomer K.B., Crow F.W., Knoche H.W., and Gross M.L. Fast Atom Bombardment and Mass Spectrometry/Mass Spectrometry for Analysis of a Mixture of Ornithine-Containing Lipids from Thiobacillus thiooxidans. Anal. Chem 55 (1983) 1033-1036
25. Geiger O., Rohrs V., Weissenmayer B., Finan T.M., and Thomas-Oates J.E. The Regulator Gene phoB Mediates Phosphate Stress-Controlled Synthesis of the Membrane Lipid Diacylglyceryl-N,N,N-Trimethylhomoserine in Rhizobium (Sinorhizobium) meliloti. Mol. Microbiol 32 (1999) 63-73
26. Hilker D.R., Knoche H.W., and Gross M.L. Thermolysis Chemical Ionization of a Complex Polar Lipid. Biomed. Mass Spectrom 6 (1979) 356-358
27. Cerny R.L., Tomer K.B., and Gross M.L. Desorption Ionization Combined with Tandem Mass Spectrometry: Advantages for Investigating Complex Lipids, Disaccharides, and Organometallic complexes. Org. Mass Spectrom 21 (1986) 655-660
28. + ions. J. Am. Soc. Mass Spectrom 9 (1998) 945-956
29. Zhen Y., Qian J., Follmann K., Hayward T., Nilsson T., Dahn M., Hilmi Y., Hamer A.G., Hosler J.P., and Ferguson-Miller S. Overexpression and Purification of Cytochrome c oxidase from Rhodobacter sphaeroides. Protein Expr. Purif. 13 (1998) 326-336
30. Awasthi Y.C., Chuang T.F., Keenan T.W., and Crane F.L. Tightly Bound Cardiolipin in Cytochrome Oxidase. Biochim. Biophys. Acta Bioenerg 226 (1971) 42-52
31. Fahy E., Subramaniam S., Brown H.A., Glass C.K., Merrill Jr. A.H., Murphy R.C., Raetz C.R.H., Russell D.W., Seyama Y., Shaw W., Shimizu T., Spener F., van Meer G., Van Nieuwenhze M.S., White S.H., Witztum J.L., and Dennis E.A. A Comprehensive Classification System for Lipids. J. Lipid Res 46 (2005) 839-862
32. - Parent Anions of Underivatized Peptides: An Aid to Structure Determination and Some Unusual Negative Ion Cleavages. Mass Spectrom. Rev 21 (2002) 87-107
33. Bowie J.H. The Fragmentations of Even-Electron Organic Negative Ions. Mass Spectrom. Rev 9 (1990) 349-379
34. Eckersley M., Bowie J.H., and Hayes R.N. Collision-Induced Dissociations of Deprotonated &;α-Amino Acids. The Occurrence of Specific Proton Transfers Preceding Fragmentation. Int. J. Mass Spectrom. Ion Processes 93 (1989) 199-213
35. Klug R.M., and Benning C. Two Enzymes of Diacylglyceryl-O-4′-(N,N,N-Trimethyl)-Homoserine Biosynthesis are Encoded by btaA and btaB in the purple bacterium. Rhodobacter sphaeroides. Proc. Natl. Acad. Sci. U.S.A 98 (2001) 5910-5915
36. O'Hair R.A.J. The Role of Nucleophile-Electrophile Interactions in the Unimolecular and Bimolecular Gas-Phase Ion Chemistry of Peptides and Related Systems. J. Mass Spectrom 35 (2000) 1377-1381
37. Grogan D.W., and Cronan J.E.J. Cyclopropane Ring Formation in Membrane Lipids of Cacteria. Microbiol. Mol. Biol. Rev 61 (1997) 429-441
38. Froelich J.M., and Reid G.E. The Origin and Control of Ex Vivo Oxidative Peptide Modifications Prior to Mass Spectrometry Analysis. Proteomics 8 (2008) 1334-1345