Biochemical characterization of dTDP-D-Qui4N and dTDP-D-Qui4NAc biosynthetic pathways in Shigella dysenteriae type 7 and Escherichia coli O7

Journal of Bacteriology

Volumn 189, Issue 23, 2007, Pages 8626-8635

  Wang, Ying ^a,b   Xu, Yanli ^a,b   Perepelov, Andrei V ^c   Qi, Yuanyuan ^a,b   Knirel, Yuriy A ^c   Wang, Lei ^a,b   Feng, Lu ^a,b  

^a NANKAI UNIVERSITY   (China)

^b TEDA   (China)

^c N D ZELINSKY INSTITUTE OF ORGANIC CHEMISTRY   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

4 (N ACETYLGLYCYL)AMINO 4,6 DIDEOXY DEXTRO GLUCOSE; 4 ACETAMIDO 4,6 DIDEOXY DEXTRO GLUCOSE; ACYLTRANSFERASE; GLUCOSE 1 PHOSPHATE THYMIDYLTRANSFERASE; HYDROLYASE; POLYSACCHARIDE; THYMIDINE DIPHOSPHATE; THYMIDINE DIPHOSPHATE 4 KETO 6 DEOXY DEXTRO GLUCOSE AMINOTRANSFERASE; THYMIDINE DIPHOSPHATE DEXTRO GLUCOSE 4,6 DEHYDRATASE; TRANSFERASE; UNCLASSIFIED DRUG;

ARTICLE; BIOSYNTHESIS; CAPILLARY ELECTROPHORESIS; CATALYSIS; CHEMICAL STRUCTURE; CONTROLLED STUDY; ELECTROSPRAY MASS SPECTROMETRY; ENZYME MECHANISM; ENZYME PURIFICATION; ESCHERICHIA COLI; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; NUCLEOTIDE SEQUENCE; PRIORITY JOURNAL; PROTEIN EXPRESSION; SHIGELLA DYSENTERIAE;

AMINO ACID SEQUENCE; BACTERIAL PROTEINS; CARBOHYDRATE CONFORMATION; DEOXY SUGARS; ENZYME STABILITY; ESCHERICHIA COLI; GENE EXPRESSION REGULATION, BACTERIAL; GLUCOSE; KINETICS; MASS SPECTROMETRY; MOLECULAR SEQUENCE DATA; O ANTIGENS; SHIGELLA DYSENTERIAE; TEMPERATURE; THYMINE NUCLEOTIDES;

ESCHERICHIA COLI; SHIGELLA DYSENTERIAE;

EID: 36749026535     PISSN: 00219193     EISSN: None     Source Type: Journal    
DOI: 10.1128/JB.00777-07     Document Type: Article

References (39)

1. Ahlert, J., J. Distler, K. Mansouri, and W. Piepersberg. 1997. Identification of stsC, the gene encoding the L-glutamine: scyllo-inosose amino-transferase from streptomycin-producing Streptomycetes. Arch. Microbiol. 168:102-113.
2. Albermann, C., and W. Piepersberg. 2001. Expression and identification of the RfbE protein from Vibrio cholerae O1 and its use for the enzymatic synthesis of GDP-D-perosamine. Glycobiology 11:655-661.
3. Bastin, D. A., and P. R. Reeves. 1995. Sequence and analysis of the O antigen gene (rfb) cluster of Escherichia coli O111. Gene 164:17-23.
4. Bax, A., and D. G. Davis 1985. MLEV-17 based two-dimensional homonuclear magnetization transfer spectroscopy. J. Magn. Reson. 65:355-360.
5. Breazeale, S. D., A. A. Ribeiro, and C. R. Raetz. 2003. Origin of lipid A species modified with 4-amino-4-deoxy-L-arabinose in polymyxin-resistant mutants of Escherichia coli. An aminotransferase (ArnB) that generates UDP-4-deoxyl-L-arabinose. J. Biol. Chem. 278:24731-24739.
6. Caroff, M., D. Karibian, J. M. Cavaillon, and N. Haeffner-Cavaillon. 2002. Structural and functional analyses of bacterial lipopolysaccharides. Microbes Infect. 4:915-926.
7. Chen, F., G. M. Evins, W. L. Cook, R. Almeida, N. Hargrett-Bean, and I. K. Wachsmuth. 1991. Genetic diversity among toxigenic and nontoxigenic Vibrio cholerae O1 isolated from the western hemisphere. Epidemiol. Infect. 107:225-233.
8. Dhillon, N., R. S. Hale, J. Cortes, and P. F. Leadlay. 1989. Molecular characterization of a gene from Saccharopolyspora erythraea (Streptomyces erythraeus) which is involved in erythromycin biosynthesis. Mol. Microbiol. 3:1405-1414.
9. Erridge, C., E. Bennett-Guerrero, and I. Poxton. 2002. Structure and function of lipopolysaccharides. Microbes Infect. 4:837-851.
10. Feng, L., J. Tao, H. Guo, J. Xu, Y. Li, F. Rezwan, P. Reeves, and L. Wang. 2004. Structure of the Shigella dysenteriae 7 O antigen gene cluster and identification of its antigen specific genes. Microb. Pathog. 36:109-115.
11. Graninger, M., B. Kneidinger, K. Bruno, A. Scheberl, and P. Messner. 2002. Homologs of the Rml enzymes from Salmonella enterica are responsible for dTDP-beta-L-rhamnose biosynthesis in the gram-positive thermophile Aneurinibacillus thermoaerophilus DSM 10155. Appl. Environ. Microbiol. 68:3708-3715.
12. Hwang, B. Y., H. J. Lee, Y. H. Yang, H. S. Joo, and B. G. Kim. 2004. Characterization and investigation of substrate specificity of the sugar aminotransferase WecE from E. coli K12. Chem. Biol. 11:915-925.
13. Kharel, M. K., D. B. Basnet, H. C. Lee, K. Liou, J. S. Woo, B. G. Kim, and J. K. Sohng. 2004. Isolation and characterization of the tobramycin biosynthetic gene cluster from Streptomyces tenebrarius. FEMS Microbiol. Lett. 230:185-190.
14. Kharel, M. K., B. Subba, H. C. Lee, K. Liou, and J. K. Sohng. 2005. Characterization of L-glutamine:2-deoxy-scyllo-inosose aminotransferase (tbmB) from Streptomyces tenebrarius. Bioorg. Med. Chem. Lett. 15:89-92.
15. Kneidinger, B., S. Larocque, J. Brisson, N. Cadotte, and J. Lam. 2003. Biosynthesis of 2-acetamido-2,6-dideoxy-L-hexoses in bacteria follows a pattern distinct from those of the pathways of 6-deoxy-L- hexoses. Biochem. J. 371:989-995.
16. Kneidinger, B., K. O'Riordan, J. Li, J. Brisson, J. Lee, and J. Lam. 2003. Three highly conserved proteins catalyze the conversion of UDP-N-acetyl-D-glucosamine to precursors for the biosynthesis of O antigen in Pseudomonas aeruginosa O11 and capsule in Staphylococcus aureus type 5. J. Biol. Chem. 278:3615-3627.
17. Knirel, Y. A., V. V. Dashunin, A. S. Shashkov, N. K. Kochetkov, B. A. Dmitriev, and I. L. Hofman. 1988. Somatic antigens of Shigella: structure of the O-specific polysaccharide chain of the Shigella dysenteriae type 7 lipopolysaccharide. Carbohydr. Res. 179:51-60.
18. Lerouge, I., and J. Vanderleyden. 2002. O-antigen structural variation: mechanisms and possible roles in animal/plant-microbe interactions. FEMS Microbiol. Rev. 26:17-47.
19. L'vov, V. L., A. S. Shashkov, B. A. Dmitriev, N. K. Kochetkov, B. Jann, and K. Jann. 1984. Structural studies of the O-specific side chain of the lipopolysaccharide from Escherichia coli O7. Carbohydr. Res. 126:249-259.
20. Marolda, C. L., M. F. Feldman, and M. A. Valvano. 1999. Genetic organization of the O7-specific lipopolysaccharide biosynthesis cluster of Escherichia coli VW187 (O7:K1). Microbiology 145:2485-2495.
21. Matsuhashi, M., and J. L. Strominger. 1966. Thymidine diphosphate 4-acetamido-4,6-dideoxyhexoses III. Purification and properties of thymidine diphosphate 4-keto-6-deoxy-D-glucose transaminase from Escherichia coli strain B. J. Biol. Chem. 241:4738-4744.
22. McNally, D., I. Schoenhofen, E. Mulrooney, D. Whitfield, E. Vinogradov, J. Lam, S. Logan, and J. Brisson. 2006. Identification of labile UDP-ketosugars in Helicobacter pylori, Campylobacter jejuni and Pseudomonas aeruginosa: key metabolites used to make glycan virulence factors. Chem. Biol. Chem. 7:1865-1868.
23. Merson-Davies, L. A., and E. Cundliffe. 1994. Analysis of five tylosin biosynthetic genes from the tylIBA region of the Streptomyces fradiae genome. Mol. Microbiol. 13:349-355.
24. Nakano, Y., N. Suzuki, Y. Yoshida, T. Nezu, Y. Yamashita, and T. Koga. 2000. Thymidine diphosphate-6-deoxy-L-lyxo-4-hexulose reductase synthesizing dTDP-6-deoxy-L-talose from Actinobacillus actinomycetemcomitans. J. Biol. Chem. 275:6806-6812.
25. Nataro, J. P., and J. B. Kaper. 1998. Diarrheagenic Escherichia coli. Clin. Microbiol. Rev. 11:142-201.
26. Niyogi, S. K. 2005. Shigellosis. J. Microbiol. 43:133-143.
27. Obhi, R. K., and C. Creuzenet. 2005. Biochemical characterization of the Campylobacter jejuni Cj1294, a novel UDP-4-keto-6-deoxy-GlcNAc amino-transferase that generates UDP-4-amino-4,6-dideoxy-GalNAc. J. Biol. Chem. 280:20902-20908.
28. Parolis, H., L. A. Parolis, and G. Olivieri. 1997. Structural studies on the Shigella-like Escherichia coli O121 O-specific polysaccharide. Carbohydr. Res. 303:319-325.
29. Perepelov, A. V., D. Babicka, S. N. Senchenkova, A. S. Shashkov, H. Moll, A. Rozalski, U. Zahringer, and Y. A. Knirel. 2001. Structure of the O-specific polysaccharide of Proteus vulgaris O4 containing a new component of bacterial polysaccharides, 4,6-dideoxy-4-{N-[(R)-3-hydroxybutyryl]- L-alanyl}amino-D-glucose. Carbohydr. Res. 331:195-202.
30. Pfoestl, A., A. Hofinger, P. Kosma, and P. Messner. 2003. Biosynthesis of dTDP-3-acetamido-3,6-dideoxy-alpha-D-galactose in Aneurinibacillus thermoaerophilus L420-91T. J. Biol. Chem. 278:26410-26417.
31. Reeves, P. R. 1995. Role of O-antigen variation in the immune response. Trends Microbiol. 3:381-386.
32. Reeves, P. R., and L. Wang. 2002. Genomic organization of LPS-specific loci. Curr. Top. Microbiol. Immunol. 264:109-135.
33. Stenutz, R., A. Weintraub, and G. Widmalm. 2006. The structures of Escherichia coli O-polysaccharide antigens. FEMS Microbiol. Rev. 30:382-403.
34. Stroeher, U. H., L. E. Karageorgos, M. H. Brown, R. Morona, and P. A. Manning. 1995. A putative pathway for perosamine biosynthesis is the first function encoded within the rfb region of Vibrio cholerae O1. Gene 166:33-42.
35. Sweet, C. R., A. A. Ribeiro, and C. R. Raetz. 2004. Oxidation and transamination of the 3″-position of UDP-N-acetylglucosamine by enzymes from Acidithiobacillus ferrooxidans. Role in the formation of lipid a molecules with four amide-linked acyl chains. J. Biol. Chem. 279:25400-25410.
36. Vijayakumar, S., A. Merkx-Jacques, D. B. Ratnayake, I. Gryski, R. K. Obhi, S. Houle, C. M. Dozois, and C. Creuzenet. 2006. Cj1121c, a novel UDP-4-keto-6-deoxy-GlcNAc C-4 aminotransferase essential for protein glycosylation and virulence in Campylobacter jejuni. J. Biol. Chem. 281:27733-27743.
37. Volchegursky, Y., Z. Hu, L. Katz, and R. McDaniel. 2000. Biosynthesis of the anti-parasitic agent megalomicin: transformation of erythromycin to megalomicin in Saccharopolyspora erythraea. Mol. Microbiol. 37:752-762.
38. Yatsuyanagi, J., S. Saito, and I. Ito. 2002. A case of hemolytic-uremic syndrome associated with Shiga toxin 2-producing Escherichia coli O121 infection caused by drinking water contaminated with bovine feces. Jpn. J. Infect. Dis. 55:174-176.
39. Yoshida, Y., Y. Nakano, T. Nezu, Y. Yamashita, and T. Koga. 1999. A novel NDP-6-deoxyhexosyl-4-ulose reductase in the pathway for the synthesis of thymidine diphosphate-D-fucose. J. Biol. Chem. 274:16933-16939.