Chemical structure of bacteriovorax stolpii lipid A

Lipids

Volumn 45, Issue 2, 2010, Pages 189-198

  Beck, Sebastian ^a,b   Müller, Frederic D ^a,b   Strauch, Eckhard ^b   Brecker, Lothar ^c   Linscheid, Michael W ^a  

^a HUMBOLDT UNIVERSITY   (Germany)

^b FEDERAL INSTITUTE FOR RISK ASSESSMENT   (Germany)

^c UNIVERSITY OF VIENNA   (Austria)

Author keywords

Bacteriovorax; Bdellovibrionales; Endotoxin; Lipid A; Mass spectrometry; NMR spectroscopy; Predatory prokaryotes

Indexed keywords

ENDOTOXIN; ETHANOLAMINE DERIVATIVE; GLUCOPYRANOSIDE; HYDROXY FATTY ACID; LIPID A; LIPOPOLYSACCHARIDE; PHOSPHATE; SUGAR;

ARTICLE; BACTERIAL STRAIN; BACTERIOVORACACEAE; BACTERIOVORAX STOLPII; BACTERIUM; BDELLOVIBRIONALES; CHEMICAL STRUCTURE; ELECTROSPRAY MASS SPECTROMETRY; MASS FRAGMENTOGRAPHY; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLYACRYLAMIDE GEL ELECTROPHORESIS;

DELTAPROTEOBACTERIA; FATTY ACIDS; LIPID A; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; SPECTROMETRY, MASS, MATRIX-ASSISTED LASER DESORPTION-IONIZATION;

BACTERIOVORACACEAE; BACTERIOVORAX; BACTERIOVORAX STOLPII; BDELLOVIBRIONACEAE; BDELLOVIBRIONALES; PROKARYOTA;

EID: 77949271417     PISSN: 00244201     EISSN: 15589307     Source Type: Journal    
DOI: 10.1007/s11745-010-3383-6     Document Type: Article

References (41)

1. AR Snyder HN Williams ML Baer KE Walker OC Stine 2002 16S rDNA sequence analysis of environmental Bdellovibrio-and-like organisms (BALO) reveals extensive diversity Int J Syst Evol Microbiol 52 2089 2094 10.1099/ijs.0.02261-0 1:CAS:528:DC%2BD3sXht12iuw%3D%3D 12508873 (Pubitemid 36004189)
2. H Stolp H Petzold 1962 Untersuchungen über einen obligat parasitischen Mikroorganismus mit lytischer Aktivität für Pseudomonas-Bakterien Phytopathol Z 45 364 390 10.1111/j.1439-0434.1962.tb02050. x
3. H Stolp MP Starr 1963 Bdellovibrio bacteriovorus gen et sp. n., a predatory, ectoparasitic, and bacteriolytic microorganism Antonie Van Leeuwenhoek 29 217 248 10.1007/BF02046064 1:STN:280:DyaF2c%2Fis1SrtA%3D%3D 14068454
4. ML Baer J Ravel J Chun RT Hill HN Williams 2000 A proposal for the reclassification of Bdellovibrio stolpii and Bdellovibrio starrii into a new genus, Bacteriovorax gen. nov. as Bacteriovorax stolpii comb. nov. and Bacteriovorax starrii comb. nov., respectively Int J Syst Evol Microbiol 50 Pt 1 219 224 1:CAS:528:DC%2BD3cXhtVeqtLw%3D 10826807
5. ML Baer J Ravel SA Pineiro D Guether-Borg HN Williams 2004 Reclassification of salt-water Bdellovibrio sp. as Bacteriovorax marinus sp. nov. and Bacteriovorax litoralis sp. nov Int J Syst Evol Microbiol 54 Pt 4 1011 1016 10.1099/ijs.0.02458-0 1:CAS:528:DC%2BD2cXnt1Gisr0%3D 15280263 (Pubitemid 39139812)
6. Y Davidov E Jurkevitch 2004 Diversity and evolution of Bdellovibrio-and-like organisms(BALOs), reclassification of Bacteriovorax starrii as Peredibacter starrii gen. nov., comb. nov., and description of the Bacteriovorax-Peredibacter clade as Bacteriovoracaceae fam. nov Int J Syst Evol Microbiol 54 Pt 5 1439 1452 10.1099/ijs.0.02978-0 1:CAS:528:DC%2BD2cXptVOls78%3D 15388693 (Pubitemid 39359954)
7. E Jurkevitch D Minz B Ramati G Barel 2000 Prey range characterization, ribotyping, and diversity of soil and rhizosphere Bdellovibrio spp isolated on phytopathogenic bacteria Appl Environ Microbiol 66 2365 2371 10.1128/AEM.66.6.2365-2371.2000 1:CAS:528:DC%2BD3cXjvFWgu7s%3D 10831412 (Pubitemid 30353939)
8. D Schwudke E Strauch M Krueger B Appel 2001 Taxonomic studies of predatory bdellovibrios based on 16S rRNA analysis, ribotyping and the hit locus and characterization of isolates from the gut of animals Syst Appl Microbiol 24 385 394 10.1078/0723-2020-00042 1:CAS:528:DC%2BD38XhsFSitbk%3D 11822674
9. S Rendulic P Jagtap A Rosinus M Eppinger C Baar C Lanz H Keller C Lambert KJ Evans A Goesmann, et al. 2004 A predator unmasked: life cycle of Bdellovibrio bacteriovorus from a genomic perspective Science 303 689 692 10.1126/science.1093027 1:CAS:528:DC%2BD2cXmvVKlsA%3D%3D 14752164 (Pubitemid 38141638)
10. D Schwudke M Linscheid E Strauch B Appel U Zahringer H Moll M Muller L Brecker S Gronow B Lindner 2003 The obligate predatory Bdellovibrio bacteriovorus possesses a neutral lipid A containing alpha-d-mannoses that replace phosphate residues: similarities and differences between the lipid As and the lipopolysaccharides of the wild type strain B. bacteriovorus HD100 and its host-independent derivative HI100 J Biol Chem 278 27502 27512 10.1074/jbc.M303012200 1:CAS:528:DC%2BD3sXlsFKksbg%3D 12743115 (Pubitemid 36899933)
11. DL Diedrich CF Denny T Hashimoto SF Conti 1970 Facultatively parasitic strain of Bdellovibrio bacteriovorus J Bacteriol 101 989 996 1:STN:280:DyaE3c7lslOjsw%3D%3D 4908792
12. RJ Seidler M Mandel JN Babtist 1972 Molecular heterogeneity of the bdellovibrios: evidence of two new species J Bacteriol 109 209 217 1:CAS:528:DyaE38Xls1ChsA%3D%3D
13. S Steiner SF Conti RL Lester 1973 Occurrence of phosphonosphingolipids in Bdellovibrio bacteriovorus strain UKi2 J Bacteriol 116 1199 1211 1:CAS:528:DyaE2cXisVGruw%3D%3D 4752938
14. Y Watanabe M Nakajima T Hoshino K Jayasimhulu EE Brooks ES Kaneshiro 2001 A novel sphingophosphonolipid head group 1-hydroxy-2-aminoethyl phosphonate in Bdellovibrio stolpii Lipids 36 513 519 10.1007/s11745-001-0751-3 1:CAS:528:DC%2BD3MXks1Gkt7s%3D 11432465
15. K Jayasimhulu SM Hunt ES Kaneshiro Y Watanabe J-L Giner 2006 Detection and identification of Bacteriovorax stolpii UKi2 sphingophosphonolipid molecular species J Am Soc Mass Spectrom 18 394 403 10.1016/j.jasms.2006.10.014 17123828
16. S Beck D Schwudke B Appel M Linscheid E Strauch 2005 Characterization of outer membrane protein fractions of Bdellovibrionales FEMS Microbiol Lett 243 211 217 10.1016/j.femsle.2004.12.006 1:CAS:528:DC%2BD2MXmsVGjsg%3D%3D 15668021 (Pubitemid 40164409)
17. C Galanos O Luderitz O Westphal 1969 A new method for the extraction of R lipopolysaccharides Eur J Biochem 9 245 249 10.1111/j.1432-1033.1969.tb00601.x 1:CAS:528:DyaF1MXksVKms7o%3D 5804498
18. UK Laemmli 1970 Cleavage of structural proteins during the 455 assembly of the head of bacteriophage T4 Nature 227 680 685 10.1038/227680a0 1:CAS:528:DC%2BD3MXlsFags7s%3D 5432063
19. CM Tsai CE Frasch 1982 A sensitive silver stain for detecting lipopolysaccharides in polyacrylamide gels Anal Biochem 119 115 119 10.1016/0003-2697(82)90673-X 1:CAS:528:DyaL38Xot1agsg%3D%3D 6176137
20. K Bryn E Jantzen 1982 Analysis of lipopolysaccharides by methanolysis, trifluoroacetylation, and gas chromatography on a fused-silica capillary column J Chromatogr 240 405 413 10.1016/S0021-9673(00)99620-1 1:CAS:528: DyaL38Xkt1SisL0%3D
21. GJ Gerwig JP Kamerling JF Vliegenthart 1978 Determination of the d and l configuration of neutral monosaccharides by high-resolution capillary G.L.C Carbohydr Res 62 349 357 10.1016/S0008-6215(00)80881-2 1:CAS:528: DyaE1cXksVCisro%3D
22. GJ Gerwig JP Kamerling JF Vliegenthart 1979 Determination of the absolute configuration of mono-saccharides in complex carbohydrates by capillary G.L.C Carbohydr Res 77 1 17 10.1016/S0008-6215(00)83788-X 1:CAS:528: DyaL3cXns1yhtg%3D%3D
23. CRH Raetz 1990 Biochemistry of endotoxins Annu Rev Biochem 59 129 170 10.1146/annurev.bi.59.070190.001021 1:CAS:528:DyaK3cXlvVOltrg%3D 1695830
24. B Domon CE Costello 1988 A systematic nomenclature of carbohydrate fragmentation in FAB-MS/MS spectra of glycoconjugates Glycoconj J 5 397 409 10.1007/BF01049915 1:CAS:528:DyaL1MXitVyks7g%3D (Pubitemid 19031141)
25. S Sforza A Silipo A Molinaro R Marchelli M Parrilli R Lanzetta 2004 Determination of fatty acid positions in native lipid A by positive and negative electrospray ionization mass spectrometry J Mass Spectrom 39 378 383 10.1002/jms.598 1:CAS:528:DC%2BD2cXjtlKrtbk%3D 15103651 (Pubitemid 38515351)
26. MM Corsaro FD Piaz R Lanzetta T Naldi M Parrilli 2004 Structure of lipid A from Pseudomonas corrugata by electrospray ionization quadrupole time-of-flight tandem mass spectrometry Rapid Commun Mass Spectrom 18 853 858 10.1002/rcm.1414 1:CAS:528:DC%2BD2cXjsFKgt7c%3D 15095352
27. L Brecker 2003 Nuclear magnetic resonance of lipid A-the influence of solvents on spin relaxation and spectral quality Chem Phys Lipids 125 27 39 10.1016/S0009-3084(03)00055-0 1:CAS:528:DC%2BD3sXos1GltLs%3D 14625073 (Pubitemid 37414803)
28. Y Wang RI Hollingsworth 1995 A solvent system for the 479 high-resolution proton nuclear magnetic resonance spectroscopy of membrane lipids Anal Biochem 225 242 251 10.1006/abio.1995.1149 1:CAS:528:DyaK2MXktFyqu74%3D 7762786
29. AA Ribeiro ZM Zhou CRH Raetz 1999 Multi-dimensional NMR structural analyses of purified Lipid X and Lipid A (endotoxin) Magn Reson Chem 37 620 630 10.1002/(SICI)1097-458X(199909)37:9<620::AID-MRC517>3.0.CO;2-Q 1:CAS:528:DyaK1MXmtFCgt7w%3D
30. 3-treated Escherichia coli versus kdsA mutants of Salmonella typhimurium J Biol Chem 275 13542 13551 10.1074/jbc.275.18.13542 1:CAS:528:DC%2BD3cXjtFyktL4%3D 10788469 (Pubitemid 30257420)
31. ET Rietschel 1976 Absolute configuration of 3-hydroxy fatty acids present in lipopolysaccharides from various bacterial groups Eur J Biochem 64 423 428 10.1111/j.1432-1033.1976.tb10318.x 1:CAS:528:DyaE28XkvVyrtLc%3D 1278168
32. T Touzé AX Tran JV Hankins D Mengin-Lecreulx SM Trent 2008 Periplasmic phosphorylation of lipid A is linked to the synthesis of undecaprenyl phosphate Mol Microbiol 67 264 277 18047581
33. SM Zughaier B Lindner J Howe P Garidel MHJ Koch K Brandenburg DS Stephens 2007 Physicochemical characterization and biological activity of lipooligosaccharides and lipid A from Neisseria meningitidis J Endotoxin Res 13 343 357 10.1177/0968051907084435 1:CAS:528:DC%2BD1cXhvF2gt7g%3D 18182462
34. VA Kulshin U Zaehringer B Lindner CE Frasch CM Tsai BA Dmitriev ET Rietschel 1992 Structural characterization of the lipid A component of pathogenic Neisseria meningitidis J Bacteriol 174 1793 1800 1:CAS:528: DyaK38XitFSrt7s%3D 1548229
35. A Choma P Sowinski 2004 Characterization of Mesorhizobium huakuii lipid A containing both d-galacturonic acid and phosphate residues Eur J Biochem 271 1310 1322 10.1111/j.1432-1033.2004.04038.x 1:CAS:528:DC%2BD2cXjtFKgtL8%3D 15030481 (Pubitemid 38519609)
36. NL Que-Gewirth AA Ribeiro SR Kalb RJ Cotter DM Bulach B Adler IS Girons C Werts CR Raetz 2004 A methylated phosphate group and four amide-linked acyl chains in Leptospira interrogans lipid A. The membrane anchor of an unusual lipopolysaccharide that activates TLR2 J Biol Chem 279 25420 25429 10.1074/jbc.M400598200 1:CAS:528:DC%2BD2cXksFygsLs%3D 15044492 (Pubitemid 38756799)
37. LD Varbanets 1994 The endotoxins of Gram-negative bacteria: their structure and biological role Mikrobiol Z 56 76 97 1:CAS:528:DyaK2MXlt1Ggs7k%3D 7952230
38. C Alexander ET Rietschel 2001 Bacterial lipopolysaccharides and innate immunity J Endotoxin Res 7 167 202 1:CAS:528:DC%2BD3MXns1yrtr4%3D 11581570
39. ET Rietschel T Kirikae FU Schade U Mamat G Schmidt H Loppnow AJ Ulmer U Zahringer U Seydel F Di Padova, et al. 1994 Bacterial endotoxin: molecular relationships of structure to activity and function FASEB J 8 217 225 1:CAS:528:DyaK2cXhvVCksL4%3D 8119492
40. S Hase ET Rietschel 1976 Isolation and analysis of the lipid A backbone. Lipid A structure of lipopolysaccharides from various bacterial groups Eur J Biochem 63 101 107 10.1111/j.1432-1033.1976.tb10212.x 1:CAS:528: DyaE28XhsVKmsrY%3D 770165
41. ET Rietschel L Brade FU Schade U Seydel U Zahringer U Mamat G Schmidt AJ Ulmer H Loppnow HD Flad, et al. 1993 Bacterial endotoxins: relationship between chemical structure and biological effect Immun Infekt 21 26 35 1:CAS:528:DyaK2cXmsFeitrk%3D 8340135