Global and targeted lipid analysis of Gemmata obscuriglobus reveals the presence of lipopolysaccharide, a signature of the classical Gram-negative outer membrane

Journal of Bacteriology

Volumn 198, Issue 2, 2016, Pages 221-236

  Mahat, Rajendra ^a,c   Seebart, Corrine ^b   Basile, Franco ^a   Ward, Naomi L ^b  

^a UNIVERSITY OF WYOMING   (United States)

^b UNIVERSITY OF WYOMING   (United States)

^c Sinclair Wyoming Refining Company   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3 DEOXY MANNO OCTULOSONIC ACID; CARBOHYDRATE; GLUCOSAMINE; HEPTOSE; HEXOSE; HYDROXY FATTY ACID; LIPID A; LIPOPOLYSACCHARIDE; POLYUNSATURATED FATTY ACID; UNSATURATED FATTY ACID;

ARTICLE; BACTERIAL MEMBRANE; CHEMICAL STRUCTURE; CONTROLLED STUDY; ELECTROPHORESIS; GEMMATA; GEMMATA OBSCURIGLOBUS; LIPID ANALYSIS; MASS FRAGMENTOGRAPHY; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; NONHUMAN; OUTER MEMBRANE; PLANCTOMYCETES; PRIORITY JOURNAL; STAINING; CELL MEMBRANE; CHEMISTRY; CLASSIFICATION; CYTOLOGY; PHYSIOLOGY; PLANCTOMYCETALES;

CELL MEMBRANE; FATTY ACIDS, UNSATURATED; LIPID A; LIPOPOLYSACCHARIDES; PLANCTOMYCETALES;

EID: 84953911557     PISSN: 00219193     EISSN: 10985530     Source Type: Journal    
DOI: 10.1128/JB.00517-15     Document Type: Article

References (90)

1. Franzmann PD, Skerman VB. 1984. Gemmata obscuriglobus, a new genus and species of the budding bacteria. Antonie Van Leeuwenhoek 50:261-268. http://dx.doi.org/10.1007/BF02342136.
2. Devos DP. 2013. Gemmata obscuriglobus. Curr Biol 23:R705-R707.
3. Fuerst JA. 2013. The PVC superphylum: exceptions to the bacterial definition? Antonie Van Leeuwenhoek 104:451-466. http://dx.doi.org/10.1007/s10482-013-9986-1.
4. Reynaud EG, Devos DP. 2011. Transitional forms between the three domains of life and evolutionary implications. Proc Biol Sci 278:3321-3328. http://dx.doi.org/10.1098/rspb.2011.1581.
5. Fuerst JA, Sagulenko E. 2011. Beyond the bacterium: planctomycetes challenge our concepts of microbial structure and function. Nat Rev Microbiol 9:403-413. http://dx.doi.org/10.1038/nrmicro2578.
6. Fuerst JA. 2005. Intracellular compartmentation in planctomycetes. Annu Rev Microbiol 59:299-328. http://dx.doi.org/10.1146/annurev.micro.59.030804.121258.
7. Santarella-Mellwig R, Pruggnaller S, Roos N, Mattaj IW, Devos DP. 2013. Three-dimensional reconstruction of bacteria with a complex endomembrane system. PLoS Biol 11:e1001565. http://dx.doi.org/10.1371/journal.pbio.1001565.
8. Pearson A, Budin M, Brocks JJ. 2003. Phylogenetic and biochemical evidence for sterol synthesis in the bacterium Gemmata obscuriglobus. Proc Natl Acad Sci U S A 100:15352-15357. http://dx.doi.org/10.1073/pnas.2536559100.
9. Lamb DC, Jackson CJ, Warrilow AGS, Manning NJ, Kelly DE, Kelly SL. 2007. Lanosterol biosynthesis in the prokaryote Methylococcus capsulatus: insight into the evolution of sterol biosynthesis. Mol Biol Evol 24:1714-1721. http://dx.doi.org/10.1093/molbev/msm090.
10. Lonhienne TGA, Sagulenko E, Webb RI, Lee K-C, Franke J, Devos DP, Nouwens A, Carroll BJ, Fuerst JA. 2010. Endocytosis-like protein uptake in the bacterium Gemmata obscuriglobus. Proc Natl Acad Sci U S A 107:12883-12888. http://dx.doi.org/10.1073/pnas.1001085107.
11. Yee B, Sagulenko E, Morgan GP, Webb RI, Fuerst JA. 2012. Electron tomography of the nucleoid of Gemmata obscuriglobus reveals complex liquid crystalline cholesteric structure. Front Microbiol 3:326. http://dx.doi.org/10.3389/fmicb.2012.00326.
12. Lieber A, Leis A, Kushmaro A, Minsky A, Medalia O. 2009. Chromatin organization and radio resistance in the bacterium Gemmata obscuriglobus. J Bacteriol 191:1439-1445. http://dx.doi.org/10.1128/JB.01513-08.
13. Sagulenko E, Morgan GP, Webb RI, Yee B, Lee K-C, Fuerst JA. 2014. Structural studies of planctomycete Gemmata obscuriglobus support cell compartmentalisation in a bacterium. PLoS One 9:e91344. http://dx.doi.org/10.1371/journal.pone.0091344.
14. Lindsay MR, Webb RI, Strous M, Jetten MS, Butler MK, Forde RJ, Fuerst JA. 2001. Cell compartmentalisation in planctomycetes: novel types of structural organisation for the bacterial cell. Arch Microbiol 175:413-429. http://dx.doi.org/10.1007/s002030100280.
15. Jenkins C, Kedar V, Fuerst JA. 2002. Gene discovery within the planctomycete division of the domain Bacteria using sequence tags from genomic DNA libraries. Genome Biol 3:research0031.1-research0031.11.
16. Jeske O, Schüler M, Schumann P, Schneider A, Boedeker C, Jogler M, Bollschweiler D, Rohde M, Mayer C, Engelhardt H, Spring S, Jogler C. 2015. Planctomycetes do possess a peptidoglycan cell wall. Nat Commun 6:7116. http://dx.doi.org/10.1038/ncomms8116.
17. van Teeseling MCF, Mesman RJ, Kuru E, Espaillat A, Cava F, Brun YV, VanNieuwenhze MS, Kartal B, van Niftrik L. 2015. Anammox planctomycetes have a peptidoglycan cell wall. Nat Commun 6:6878. http://dx.doi.org/10.1038/ncomms7878.
18. Stackebrandt E, Wehmeyer U, Liesack W. 1986. 16S ribosomal RNAand cell wall analysis of Gemmata obscuriglobus, a new member of the order Planctomycetales. FEMS Microbiol Lett 37:289-292. http://dx.doi.org/10.1111/j.1574-6968.1986.tb01810.x.
19. Fuerst JA, Webb RI. 1991. Membrane-bounded nucleoid in the eubacterium Gemmata obscuriglobus. Proc Natl Acad Sci U S A 88:8184-8188. http://dx.doi.org/10.1073/pnas.88.18.8184.
20. Speth DR, van Teeseling MCF, Jetten MSM. 2012. Genomic analysis indicates the presence of an asymmetric bilayer outer membrane in Planctomycetes and Verrucomicrobia. Front Microbiol 3:304. http://dx.doi.org/10.3389/fmicb.2012.00304.
21. Paparoditis P, Västermark Å, Le AJ, Fuerst JA, Saier MH, Jr. 2014. Bioinformatic analyses of integral membrane transport proteins encoded within the genome of the Planctomycetes species, Rhodopirellula baltica. Biochim Biophys Acta 1838:193-215. http://dx.doi.org/10.1016/j.bbamem.2013.08.007.
22. Amat F, Comolli LR, Nomellini JF, Moussavi F, Downing KH, Smit J, Horowitz M. 2010. Analysis of the intact surface layer of Caulobacter crescentus by cryo-electron tomography. J Bacteriol 192:5855-5865. http://dx.doi.org/10.1128/JB.00747-10.
23. van Teeseling MCF, de Almeida NM, Klingl A, Speth DR, Op den Camp HJM, Rachel R, Jetten MSM, van Niftrik L. 2014. A new addition to the cell plan of anammox bacteria: "Candidatus Kuenenia stuttgartiensis" has a protein surface layer as the outermost layer of the cell. J Bacteriol 196:80-89. http://dx.doi.org/10.1128/JB.00988-13.
24. Raetz CRH, Whitfield C. 2002. Lipopolysaccharide endotoxins. Annu Rev Biochem 71:635-700. http://dx.doi.org/10.1146/annurev.biochem.71.110601.135414.
25. Sutcliffe IC. 2010. A phylum level perspective on bacterial cell envelope architecture. Trends Microbiol 18:464-470. http://dx.doi.org/10.1016/j.tim.2010.06.005.
26. Kamerling JP. 2007. Comprehensive glycoscience: from chemistry to systems biology. Elsevier, Amsterdam, the Netherlands.
27. De Castro C, Parrilli M, Holst O, Molinaro A. 2010. Microbe-associated molecular patterns in innate immunity: extraction and chemical analysis of gram-negative bacterial lipopolysaccharides. 480:89-115. http://dx.doi.org/10.1016/S0076-6879(10)80005-9.
28. Caroff M, Karibian D. 2003. Structure of bacterial lipopolysaccharides. Carbohydr Res 338:2431-2447. http://dx.doi.org/10.1016/j.carres.2003.07.010.
29. Hug I, Feldman MF. 2011. Analogies and homologies in lipopolysaccharide and glycoprotein biosynthesis in bacteria. Glycobiology 21:138-151. http://dx.doi.org/10.1093/glycob/cwq148.
30. Marolda CL, Lahiry P, Vinés E, Saldías S, Valvano MA. 2006. Micromethods for the characterization of lipid A-core and O-antigen lipopolysaccharide. Methods Mol Biol 347:237-252.
31. Knirel YA, Valvano MA. 2011. Bacterial lipopolysaccharides: structure, chemical synthesis, biogenesis, and interaction with host cells. Springer, Vienna, Austria.
32. Ruiz N, Kahne D, Silhavy TJ. 2009. Transport of lipopolysaccharide across the cell envelope: the long road of discovery. Nat Rev Microbiol 7:677-683. http://dx.doi.org/10.1038/nrmicro2184.
33. Kabanov DS, Prokhorenko IR. 2010. Structural analysis of lipopolysaccharides from Gram-negative bacteria. Biochemistry (Moscow) 75:383-404. http://dx.doi.org/10.1134/S0006297910040012.
34. Trent MS. 2004. Biosynthesis, transport, and modification of lipid A. Biochem Cell Biol 82:71-86.
35. Gronow S, Brade H. 2001. Invited review: lipopolysaccharide biosynthesis: which steps do bacteria need to survive? J Endotoxin Res 7:3-23. http://dx.doi.org/10.1177/09680519010070010301.
36. Wang X, Quinn PJ. 2010. Endotoxins: structure, function and recognition. Springer Verlag, New York, NY.
37. Valvano MA, Messner P, Kosma P. 2002. Novel pathways for biosynthesis of nucleotide-activated glycero-manno-heptose precursors of bacterial glycoproteins and cell surface polysaccharides. Microbiology 148:1979-1989. http://dx.doi.org/10.1099/00221287-148-7-1979.
38. Zähringer U, Lindner B, Knirel YA, van den Akker WMR, Hiestand R, Heine H, Dehio C. 2004. Structure and biological activity of the short-chain lipopolysaccharide from Bartonella henselae ATCC 49882T. J Biol Chem 279:21046-21054. http://dx.doi.org/10.1074/jbc.M313370200.
39. Kilár A, Dörnyei Á Kocsis B. 2013. Structural characterization of bacterial lipopolysaccharides with mass spectrometry and on- and off-line separation techniques. Mass Spectrom Rev 32:90-117. http://dx.doi.org/10.1002/mas.21352.
40. Kerger BD, Mancuso CA, Nichols PD, White DC, Langworthy T, Sittig M, Schlesner H, Hirsch P. 1988. The budding bacteria, Pirellula and Planctomyces, with atypical 16S rRNA and absence of peptidoglycan, show eubacterial phospholipids and uniquely high proportions of long chain beta-hydroxy fatty acids in the lipopolysaccharide lipid A. Arch Microbiol 149:255-260. http://dx.doi.org/10.1007/BF00422014.
41. Sittig M, Schlesner H. 1993. Chemotaxonomic investigation of various prosthecate and/or budding bacteria. Syst Appl Microbiol 16:92-103. http://dx.doi.org/10.1016/S0723-2020(11)80253-5.
42. Strous M, Pelletier E, Mangenot S, Rattei T, Lehner A, Taylor MW, Horn M, Daims H, Bartol-Mavel D, Wincker P, Barbe V, Fonknechten N, Vallenet D, Segurens B, Schenowitz-Truong C, Médigue C, Collingro A, Snel B, Dutilh BE, Op den Camp HJM, van der Drift C, Cirpus I, van de Pas-Schoonen KT, Harhangi HR, van Niftrik L, Schmid M, Keltjens J, van de Vossenberg J, Kartal B, Meier H, Frishman D, Huynen MA, Mewes H-W, Weissenbach J, Jetten MSM, Wagner M, Le Paslier D. 2006. Deciphering the evolution and metabolism of an anammox bacterium from a community genome. Nature 440:790-794. http://dx.doi.org/10.1038/nature04647.
43. Yi EC, Hackett M. 2000. Rapid isolation method for lipopolysaccharide and lipid A from Gram-negative bacteria. Analyst 125:651-656. http://dx.doi.org/10.1039/b000368i.
44. El Hamidi A, Tirsoaga A, Novikov A, Hussein A, Caroff M. 2005. Microextraction of bacterial lipid A: easy and rapid method for mass spectrometric characterization. J Lipid Res 46:1773-1778. http://dx.doi.org/10.1194/jlr.D500014-JLR200.
45. Schultz E, Pugh ME. 2001. Determination of the fatty acid content of biological membranes: a highly versatile GC-MS experiment. J Chem Educ 78:944. http://dx.doi.org/10.1021/ed078p944.
46. Komagata K, Suzuki K-I. 1988. 4-Lipid and cell-wall analysis in bacterial systematics, p 161-207. In Grigorova R, Norris JR (ed), Methods in microbiology. Academic Press, San Diego, CA.
47. Rybka J, Gamian A. 2006. Determination of endotoxin by the measurement of the acetylated methyl glycoside derivative of Kdo with gas-liquid chromatography-mass spectrometry. J Microbiol Methods 64:171-184. http://dx.doi.org/10.1016/j.mimet.2005.04.029.
48. Silipo A, Lanzetta R, Amoresano A, Parrilli M, Molinaro A. 2002. Ammonium hydroxide hydrolysis: a valuable support in the MALDI-TOF mass spectrometry analysis of lipid A fatty acid distribution. J Lipid Res 43:2188-2195. http://dx.doi.org/10.1194/jlr.D200021-JLR200.
49. Basile F, Voorhees KJ, Hadfield TL. 1995. Microorganism Gram-type differentiation based on pyrolysis-mass spectrometry of bacterial fatty acid methyl ester extracts. Appl Environ Microbiol 61:1534-1539.
50. Huang JX, Azad MAK, Yuriev E, Baker MA, Nation RL, Li J, Cooper MA, Velkov T. 2012. Molecular characterization of lipopolysaccharide binding to human α-1-acid glycoprotein. J Lipids 2012:475153.
51. Lee DH, Kim S-H, Kang W, Choi YS, Lee S-H, Lee S-R, You S, Lee HK, Chang K-T, Shin E-C. 2011. Adjuvant effect of bacterial outer membrane vesicles with penta-acylated lipopolysaccharide on antigen-specific T cell priming. Vaccine 29:8293-8301. http://dx.doi.org/10.1016/j.vaccine.2011.08.102.
52. Peterson AA, Haug A, McGroarty EJ. 1986. Physical properties of shortand long-O-antigen-containing fractions of lipopolysaccharide from Escherichia coli 0111:B4. J Bacteriol 165:116-122.
53. Tan L, Grewal PS. 2002. Comparison of two silver staining techniques for detecting lipopolysaccharides in polyacrylamide gels. J Clin Microbiol 40:4372-4374. http://dx.doi.org/10.1128/JCM.40.11.4372-4374.2002.
54. Meredith TC, Aggarwal P, Mamat U, Lindner B, Woodard RW. 2006. Redefining the requisite lipopolysaccharide structure in Escherichia coli. ACS Chem Biol 1:33-42. http://dx.doi.org/10.1021/cb0500015.
55. Darveau RP, Pham T-TT, Lemley K, Reife RA, Bainbridge BW, Coats SR, Howald WN, Way SS, Hajjar AM. 2004. Porphyromonas gingivalis lipopolysaccharide contains multiple lipid A species that functionally interact with both Toll-like receptors 2 and 4. Infect Immun 72:5041-5051. http://dx.doi.org/10.1128/IAI.72.9.5041-5051.2004.
56. 2+ and pH in the modification of Salmonella lipid A after endocytosis by macrophage tumour cells. Mol Microbiol 55:425-440.
57. Kulichevskaya IS, Baulina OI, Bodelier PLE, Rijpstra WIC, Damsté JSS, Dedysh SN. 2009. Zavarzinella formosa gen. nov., sp. nov., a novel stalked, Gemmata-like planctomycete from a Siberian peat bog. Int J Syst Evol Microbiol 59:357-364. http://dx.doi.org/10.1099/ijs.0.002378-0.
58. Torella JP, Ford TJ, Kim SN, Chen AM, Way JC, Silver PA. 2013. Tailored fatty acid synthesis via dynamic control of fatty acid elongation. Proc Natl Acad Sci U S A 110:11290-11295. http://dx.doi.org/10.1073/pnas.1307129110.
59. Cronan JE. 2003. Bacterial membrane lipids: where do we stand? Annu Rev Microbiol 57:203-224. http://dx.doi.org/10.1146/annurev.micro.57.030502.090851.
60. Abe F. 2013. Dynamic structural changes in microbial membranes in response to high hydrostatic pressure analyzed using time-resolved fluorescence anisotropy measurement. Biophys Chem 183:3-8. http://dx.doi.org/10.1016/j.bpc.2013.05.005.
61. Kaneda T. 1991. Iso- and anteiso-fatty acids in bacteria: biosynthesis, function, and taxonomic significance. Microbiol Rev 55:288-302.
62. Legendre S, Letellier L, Shechter E. 1980. Influence of lipids with branched-chain fatty acids on the physical, morphological and functional properties of Escherichia coli cytoplasmic membrane. Biochim Biophys Acta 602:491-505. http://dx.doi.org/10.1016/0005-2736(80)90328-4.
63. Gill I, Valivety R. 1997. Polyunsaturated fatty acids, part 1: occurrence, biological activities and applications. Trends Biotechnol 15:401-409. http://dx.doi.org/10.1016/S0167-7799(97)01076-7.
64. Gill I, Valivety R. 1997. Polyunsaturated fatty acids, part 2: biotransformations and biotechnological applications. Trends Biotechnol 15:470-478. http://dx.doi.org/10.1016/S0167-7799(97)01077-9.
65. Siddiqui RA, Harvey K, Stillwell W. 2008. Anticancer properties of oxidation products of docosahexaenoic acid. Chem Phys Lipids 153:47-56. http://dx.doi.org/10.1016/j.chemphyslip.2008.02.009.
66. Ando Y, Kawabata Y, Narukawa K, Ota T. 1998. Demospongic acids of the marine sponge Halichondria panicea from the coast of Hokkaido, Japan. Fish Sci 64:136-139.
67. Nichols DS, McMeekin TA. 2002. Biomarker techniques to screen for bacteria that produce polyunsaturated fatty acids. J Microbiol Methods 48:161-170. http://dx.doi.org/10.1016/S0167-7012(01)00320-7.
68. Certik M, Shimizu S. 1999. Biosynthesis and regulation of microbial polyunsaturated fatty acid production. J Biosci Bioeng 87:1-14. http://dx.doi.org/10.1016/S1389-1723(99)80001-2.
69. Ferguson GP, Roop RM, Jr, Walker GC. 2002. Deficiency of a Sinorhizobium meliloti bacA mutant in alfalfa symbiosis correlates with alteration of the cell envelope. J Bacteriol 184:5625-5632. http://dx.doi.org/10.1128/jB.184.20.5625-5632.2002.
70. Ellens H, Siegel DP, Alford D, Yeagle PL, Boni L, Lis LJ, Quinn PJ, Bentz J. 1989. Membrane fusion and inverted phases. Biochemistry 28:3692-3703. http://dx.doi.org/10.1021/bi00435a011.
71. Stillwell W, Wassall SR. 2003. Docosahexaenoic acid: membrane properties of a unique fatty acid. Chem Phys Lipids 126:1-27. http://dx.doi.org/10.1016/S0009-3084(03)00101-4.
72. Wassall SR, Stillwell W. 2008. Docosahexaenoic acid domains: the ultimate non-raft membrane domain. Chem Phys Lipids 153:57-63. http://dx.doi.org/10.1016/j.chemphyslip.2008.02.010.
73. Scheuner C, Tindall BJ, Lu M, Nolan M, Lapidus A, Cheng J-F, Goodwin L, Pitluck S, Huntemann M, Liolios K, Pagani I, Mavromatis K, Ivanova N, Pati A, Chen A, Palaniappan K, Jeffries CD, Hauser L, Land M, Mwirichia R, Rohde M, Abt B, Detter JC, Woyke T, Eisen JA, Markowitz V, Hugenholtz P, Göker M, Kyrpides NC, Klenk H-P. 2014. Complete genome sequence of Planctomyces brasiliensis type strain (DSM 5305T), phylogenomic analysis and reclassification of Planctomycetes including the descriptions of Gimesia gen. nov., Planctopirus gen. nov. and Rubinisphaera gen. nov. and emended descriptions of the order Planctomycetales and the family Planctomycetaceae. Stand Genomic Sci 9:10. http://dx.doi.org/10.1186/1944-3277-9-10.
74. Wilkinson SG, Caudwell PF. 1980. Lipid composition and chemotaxonomy of Pseudomonas putrefaciens (Alteromonas putrefaciens). J Gen Microbiol 118:329-341. http://dx.doi.org/10.1099/00221287-118-2-329.
75. Moore EK, Hopmans EC, Rijpstra WIC, Villanueva L, Dedysh SN, Kulichevskaya IS, Wienk H, Schoutsen F, Sinninghe Damsté JS. 2013. Novel mono-, di-, and trimethylornithine membrane lipids in northern wetland planctomycetes. Appl Environ Microbiol 79:6874-6884. http://dx.doi.org/10.1128/AEM.02169-13.
76. Schroeder F, Jefferson JR, Kier AB, Knittel J, Scallen TJ, Wood WG, Hapala I. 1991. Membrane cholesterol dynamics: cholesterol domains and kinetic pools. Proc Soc Exp Biol Med 196:235-252. http://dx.doi.org/10.3181/00379727-196-43185.
77. Wassall SR, Stillwell W. 2009. Polyunsaturated fatty acid-cholesterol interactions: domain formation in membranes. Biochim Biophys Acta 1788:24-32. http://dx.doi.org/10.1016/j.bbamem.2008.10.011.
78. Holst O, Müller-Loennies S. 2007. Microbial polysaccharide structures, p 123-179. In KamerlingH(ed), Comprehensive glycoscience. Elsevier, Oxford, United Kingdom.
79. Chart H, Rowe B. 1991. Purification of lipopolysaccharide from strains of Yersinia enterocolitica belonging to serogroups 03 and 09. FEMS Microbiol Lett 61:341-345.
80. Palva ET, Mäkelä PH. 1980. Lipopolysaccharide heterogeneity in Salmonella Typhimurium analyzed by sodium dodecyl sulfate polyacrylamide gel electrophoresis. Eur J Biochem 107:137-143. http://dx.doi.org/10.1111/j.1432-1033.1980.tb04634.x.
81. Wang X, Quinn PJ. 2010. Lipopolysaccharide: biosynthetic pathway and structure modification. Prog Lipid Res 49:97-107. http://dx.doi.org/10.1016/j.plipres.2009.06.002.
82. Gronow S, Xia G, Brade H. 2010. Glycosyltransferases involved in the biosynthesis of the inner core region of different lipopolysaccharides. Eur J Cell Biol 89:3-10. http://dx.doi.org/10.1016/j.ejcb.2009.10.002.
83. Jann K, Jann B. 1983. The K antigens of Escherichia coli. Prog Allergy 33:53-79.
84. Sutherland IW. 1977. Surface carbohydrates of the prokaryotic cell. Academic Press, New York, NY.
85. Reife RA, Coats SR, Al-Qutub M, Dixon DM, Braham PA, Billharz RJ, Howald WN, Darveau RP. 2006. Porphyromonas gingivalis lipopolysaccharide lipid A heterogeneity: differential activities of tetra- and penta-acylated lipidAstructures on E-selectin expression and TLR4 recognition. Cell Microbiol 8:857-868. http://dx.doi.org/10.1111/j.1462-5822.2005.00672.x.
86. Rau H, Seydel U, Freudenberg M, Weckesser J, Mayer H. 1995. Lipopolysaccharide of Rhodospirillum salinarum 40: structural studies on the core and lipid A region. Arch Microbiol 164:280-289. http://dx.doi.org/10.1007/BF02529962.
87. Hollingsworth RI, Lill-Elghanian DA. 1989. Isolation and characterization of the unusual lipopolysaccharide component, 2-amino-2-deoxy-2-N-(27-hydroxyoctacosanoyl)-3-O-(3-hydroxy-tetradecanoyl)-glucohexuronic acid, and its de-O-acylation product from the free lipid A of Rhizobium trifolii ANU843. J Biol Chem 264:14039-14042.
88. Bhat UR, Carlson RW. 1992. A new method for the analysis of amidelinked hydroxy fatty acids in lipid-As from Gram-negative bacteria. Glycobiology 2:535-539. http://dx.doi.org/10.1093/glycob/2.6.535.
89. Rietschel ET, Zähringer U, Wollenweber HW, Miragliotta G, Musehold J, Lüderitz T, Schade U. 1984. Bacterial endotoxins: chemical structure and biologic activity. Am J Emerg Med 2:60-69. http://dx.doi.org/10.1016/0735-6757(84)90110-4.
90. Moran AP, Zähringer U, Seydel U, Scholz D, Stütz P, Rietschel ET. 1991. Structural analysis of the lipid A component of Campylobacter jejuni CCUG 10936 (serotype O:2) lipopolysaccharide. Description of a lipid A containing a hybrid backbone of 2-amino-2-deoxy-D-glucose and 2,3-diamino-2,3-dideoxy-D-glucose. Eur J Biochem 198:459-469.