Structural studies of the O-antigen polysaccharide from Escherichia coli O115 and biosynthetic aspects thereof

Glycobiology

Volumn 23, Issue 3, 2013, Pages 354-362

  Fontana, Carolina ^a   Ramström, Kristoffer ^a   Weintraub, Andrej ^b   Widmalm, Göran ^a  

^a STOCKHOLM UNIVERSITY   (Sweden)

^b KAROLINSKA UNIVERSITY HOSPITAL   (Sweden)

Author keywords

Escherichia coli; Glycosyltransferases; Lipopolysaccharide; O acetylation; O antigen

Indexed keywords

ACYLTRANSFERASE; BACTERIAL POLYSACCHARIDE; N ACETYLGLUCOSAMINE; O ANTIGEN;

ANTIGEN STRUCTURE; ARTICLE; BACTERIAL STRAIN; CARBOHYDRATE ANALYSIS; CARBON NUCLEAR MAGNETIC RESONANCE; ESCHERICHIA COLI; ESCHERICHIA COLI O115; HETERONUCLEAR MULTIPLE BOND CORRELATION; NITROGEN NUCLEAR MAGNETIC RESONANCE; NONHUMAN; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ANALYSIS;

ACETYLGLUCOSAMINE; ACETYLTRANSFERASES; CARBOHYDRATE CONFORMATION; CARBOHYDRATE SEQUENCE; ESCHERICHIA COLI; GLYCOSYLTRANSFERASES; MAGNETIC RESONANCE SPECTROSCOPY; MULTIGENE FAMILY; O ANTIGENS; SEQUENCE ANALYSIS, DNA;

CITRUS MAXIMA; ESCHERICHIA COLI; SHIGELLA DYSENTERIAE;

EID: 84875736232     PISSN: 09596658     EISSN: 14602423     Source Type: Journal    
DOI: 10.1093/glycob/cws161     Document Type: Article

References (42)

1. Aktan I, Sprigings KA, La Ragione RM, Faulkner LM, Paiba GA, Woodward MJ. 2004. Characterisation of attaching-effacing Escherichia coli isolated from animals at slaughter in England and Wales. Vet Microbiol. 102:43-53. (Pubitemid 39037373)
2. Ali T, Weintraub A, Widmalm G. 2008. Structural studies of the O-antigenic polysaccharides from the enteroaggregative Escherichia coli strain 87/D2 and international type strains from E. coli O128. Carbohydr Res. 343:695-702.
3. Altschul SF, Gish W, Miller W, Myers EW, Lipman DJ. 1990. Basic local alignment search tool. J Mol Biol. 215:403-410.
4. Ansaruzzaman M, Bhuiyan NA, Begum YA, Kuhn I, Nair GB, Sack DA, Svennerholm AM, Qadri F. 2007. Characterization of enterotoxigenic Escherichia coli from diarrhoeal patients in Bangladesh using phenotyping and genetic profiling. J Med Microbiol. 56:217-222.
5. Bax A, Davis DG. 1985. MLEV-17-based two-dimensional homonuclear magnetization transfer spectroscopy. J Magn Reson. 65:355-360.
6. Bax A, Summers MF. 1986. 1H and 13C assignments from sensitivityenhanced detection of heteronuclear multiple-bond connectivity by 2D multiple quantum NMR. J Am Chem Soc. 108:2093-2094.
7. Berry DS, Lynn F, Lee C-H, Frasch CE, Bash MC. 2002. Effect of O acetylation of Neisseria meningitidis serogroup A capsular polysaccharide on development of functional immune responses. Infect Immun. 70:3707-3713. (Pubitemid 34666010)
8. Bruix M, Jiménez-Barbero J, Cronet P. 1995. Determination by NMR spectroscopy of the structure and conformational features of the enterobacterial common antigen isolated from Escherichia coli. Carbohydr Res. 273: 157-170.
9. Bundle DR, Lemieux RU. 1976. Determination of anomeric configuration by NMR. Methods Carbohydr Chem. 7:79-86.
10. Chen X, Gao S, Jiao X, Liu XF. 2004. Prevalence of serogroups and virulence factors of Escherichia coli strains isolated from pigs with postweaning diarrhoea in eastern China. Vet Microbiol. 103:13-20. (Pubitemid 39286127)
11. Claridge TDW, Pérez-Victoria I. 2003. Enhanced 13C resolution in semiselective HMBC: A band-selective, constant-time HMBC for complex structure elucidation by NMR. Org Biomol Chem. 1:3632-3634.
12. Cookson AL, Hayes CM, Pearson GR, Roe JM, Wales AD, Woodward MJ. 2002. Isolation from a sheep of an attaching and effacing Escherichia coli O115:H-with a novel combination of virulence factors. J Med Microbiol. 51:1041-1049. (Pubitemid 36020724)
13. Dezfulian H, Tremblay D, Harel J. 2004. Molecular characterization of extraintestinal pathogenic Escherichia coli (ExPEC) pathogenicity islands in F165-positive E. coli strain from a diseased animal. FEMS Microbiol Lett. 238:321-332. (Pubitemid 39195157)
14. Dmitriev BA, Knirel YA, Kochetkov NK, Jann B, Jann K. 1977. Cell-wall lipopolysaccharide of the "Shigella-like" Escherichia coli 058. Eur J Biochem. 79:111-115. (Pubitemid 8188832)
15. Erbel PJA, Seidel R, Macintosh SE, Gentile LN, Amor JC, Kahn RA, Prestegard JH, McIntosh LP, Gardner KH. 2004. Cyclic enterobacterial common antigen: Potential contaminant of bacterially expressed protein preparations. J Biomol NMR. 29:199-204. (Pubitemid 38444481)
16. Fregolino E, Ivanova R, Lanzetta R, Molinaro A, Parrilli M, Paunova-Krasteva T, Stoitsova SR, Castro CD. 2012. Occurrence and structure of cyclic enterobacterial common antigen in Escherichia coli O157:H-. Carbohydr Res. 363:29-32.
17. Gilmour MW, Chui L, Chiu T, Tracz DM, Hagedorn K, Tschetter L, Tabor H, Ng LK, Louie M. 2009. Isolation and detection of Shiga toxin-producing Escherichia coli in clinical stool samples using conventional and molecular methods. J Med Microbiol. 58:905-911.
18. Jansson P-E, Kenne L, Schweda E. 1987. Nuclear magnetic resonance and conformational studies on monoacetylated methyl D-gluco-and D-galacto- pyranosides. J Chem Soc Perkin Trans. 1, 377-383.
19. Jansson P-E, Kenne L, Widmalm G. 1989. Computer-assisted structural analysis of polysaccharides with an extended version of CASPER using 1H-and 13C-N.M.R. data. Carbohydr Res. 188:169-191.
20. Kaper JB, Nataro JP, Mobley HL. 2004. Pathogenic Escherichia coli. Nat Rev Microbiol. 2:123-140. (Pubitemid 39490066)
21. Knirel YA. 2011. Structure of O-antigens. In: Knirel YA, Valvano MA, editors. Bacterial Lipopolysaccharides. Structure, Chemical Synthesis, Biogenesis and Interaction with Host Cells. Vienna: Springer. p. 41-115.
22. Konadu E, Shiloach J, Bryla DA, Robbins JB, Szu SC. 1996. Synthesis, characterization, and immunological properties in mice of conjugates composed of detoxified lipopolysaccharide of Salmonella paratyphi A bound to tetanus toxoid with emphasis on the role of O acetyls. Infect Immun. 64:2709-2715. (Pubitemid 26226837)
23. Kumar A, Ernst RR, Wüthrich K. 1980. A two-dimensional nuclear Overhauser enhancement (2D NOE) experiment for the elucidation of complete proton-proton cross-relaxation networks in biological macromolecules. Biochem Biophys Res Commun. 95:1-6.
24. Kuttel M, Mao Y, Widmalm G, Lundborg M. 2011. CarbBuilder: An adjustable tool for building 3D molecular structures of carbohydrates for molecular simulation. Proc 7th IEEE Int Conf eScience. p. 395-402.
25. Leontein K, Lönngren J. 1993. Determination of the absolute configuration of sugars by gas-liquid chromatography of their acetylated 2-octyl glycosides. Methods Carbohydr Chem. 9:87-89.
26. Liu B, Knirel YA, Feng L, Perepelov AV, Senchenkova SN, Wang Q, Reeves PR, Wang L. 2008. Structure and genetics of Shigella O antigens. FEMS Microbiol Rev. 32:627-653. (Pubitemid 351799688)
27. Lundborg M, Modhukur V, Widmalm G. 2010. Glycosyltransferase functions of E. coli O-antigens. Glycobiology. 20:366-368.
28. Nyberg NT, Duus JØ, Sørensen OW. 2005. Heteronuclear two-bond correlation: Suppressing heteronuclear three-bond or higher NMR correlations while enhancing two-bond correlations even for vanishing 2JCH. J Am Chem Soc. 127:6154-6155. (Pubitemid 40627725)
29. Olsson U, Lycknert K, Stenutz R, Weintraub A, Widmalm G. 2005. Structural analysis of the O-antigen polysaccharide from Escherichia coli O152. Carbohydr Res. 340:167-171. (Pubitemid 40023310)
30. Olsson U, Weintraub A, Widmalm G. 2008. Structural determination of the O-antigenic polysaccharide from the verocytotoxin-producing Escherichia coli O176. Carbohydr Res. 343:805-809.
31. Rojas Macias MA, Lütteke T, Widmalm G. 2012. Development of ECODAB into a relational database. In: 26 International Carbohydrate Symposium. Madrid. Poster no. P236.
32. Roslund MU, Aitio O, Wärnå J, Maaheimo H, Murzin DY, Leino R. 2008. Acyl group migration and cleavage in selectively protected β-D-galactopyranosides as studied by NMR spectroscopy and kinetic calculations. J Am Chem Soc. 130:8769-8772. (Pubitemid 351962512)
33. Saito N, Kawano M, Kobayashi T, Watanabe S, Yamada W, Yatsu J, Kawamukai K, Akiyama K. 2005. An outbreak of food poisoning caused by an enteropathogeic Escherichia coli O115:H19 in Miyagi Prefecture. Jpn J Infect Dis. 58:189-190. (Pubitemid 41460602)
34. Samuel G, Reeves P. 2003. Biosynthesis of O-antigens: Genes and pathways involved in nucleotide sugar precursor synthesis and O-antigen assembly. Carbohydr Res. 338:2503-2519. (Pubitemid 37509950)
35. Schleucher J, Schwendinger M, Sattler M, Schmidt P, Schedletzky O, Glaser SJ, Sørensen OW, Griesinger C. 1994. A general enhancement scheme in heteronuclear multidimensional NMR employing pulsed field gradients. J Biomol NMR. 4:301-306.
36. Söderman P, Jansson P-E, Widmalm G. 1998. Synthesis, NMR spectroscopy and conformational studies of the four anomeric methyl glycosides of the trisaccharide D-Glcp-(1→3)-[D-Glcp-(1→4)]-α-D-Glcp. J Chem Soc Perkin Trans. 2, 639-648. (Pubitemid 128437995)
37. Stenutz R, Weintraub A, Widmalm G. 2006. The structures of Escherichia coli O-polysaccharide antigens. FEMS Microbiol Rev. 30:382-403.
38. Svensson MV, Weintraub A, Widmalm G. 2011. Structural elucidation of the O-antigenic polysaccharide from Escherichia coli O175. Carbohydr Res. 346:449-453.
39. Wales AD, Pearson GR, Best A, Cookson AL, La Ragione RM, Roe JM, Hayes CM, Woodward MJ. 2005. Naturally acquired attaching and effacing Escherichia coli in sheep. Res Vet Sci. 78:109-115. (Pubitemid 39618902)
40. Wang Q, Ruan X, Wei D, Hu Z, Wu L, Yu T, Feng L, Wang L. 2010. Development of a serogroup-specific multiplex PCR assay to detect a set of Escherichia coli serogroups based on the identification of their O-antigen gene clusters. Mol Cell Probes. 24:286-290.
41. Wu D, Chen A, Johnson CS. 1995. An improved diffusion-ordered spectroscopy experiment incorporating bipolar-gradient pulses. J Magn Reson Ser A. 115:260-264.
42. Zaccheus MV, Broeker NK, Lundborg M, Uetrecht C, Barbirz S, Widmalm G. 2012. Structural studies of the O-antigen polysaccharide from Escherichia coli TD2158 having O18 serogroup specificity and aspects of its interaction with the tailspike endoglycosidase of the infecting bacteriophage HK620. Carbohydr Res. 357:118-125.