Characterization of the dTDP-D-fucofuranose biosynthetic pathway in Escherichia coli O52

Molecular Microbiology

Volumn 70, Issue 6, 2008, Pages 1358-1367

  Wang, Quan ^a,b   Ding, Peng ^a,b   Perepelov, Andrei V ^c   Xu, Yanli ^a,b   Wang, Ying ^a,b   Knirel, Yuriy A ^c   Wang, Lei ^a,b,d,e   Feng, Lu ^a,b,d,e  

^a NANKAI UNIVERSITY   (China)

^b BEIJING UNIVERSITY OF POSTS AND TELECOMMUNICATIONS   (China)

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

^d Tianjin Key Laboratory of Microbial Functional Genomics   (China)

^e Tianjin Research Center for Functional Genomics and Biochip   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ENZYME; FURAN DERIVATIVE; MUTASE; O ANTIGEN; THYMIDINE DIPHOSPHATE; THYMIDINE DIPHOSPHATE DEXTRO FUCOFURANOSE; UNCLASSIFIED DRUG;

ARTICLE; BACTERIAL GENE; BACTERIAL GENETICS; BACTERIAL MUTATION; BIOSYNTHESIS; CAPILLARY ELECTROPHORESIS; ELECTROSPRAY MASS SPECTROMETRY; ENZYME SUBSTRATE COMPLEX; ESCHERICHIA COLI; FCF1 GENE; FCF2 GENE; GENE EXPRESSION; GENETIC COMPLEMENTATION; KINETICS; METABOLISM; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; PROTEIN ANALYSIS; PROTEIN DETERMINATION; PROTEIN EXPRESSION; PROTEIN PURIFICATION; PROTEIN STRUCTURE;

CLONING, MOLECULAR; ESCHERICHIA COLI; ESCHERICHIA COLI PROTEINS; GENETIC COMPLEMENTATION TEST; MUTATION; NUCLEOSIDE DIPHOSPHATE SUGARS; O ANTIGENS; SUBSTRATE SPECIFICITY; SUGAR ALCOHOL DEHYDROGENASES;

ESCHERICHIA COLI; STREPTOMYCINEAE;

EID: 56749151152     PISSN: 0950382X     EISSN: 13652958     Source Type: Journal    
DOI: 10.1111/j.1365-2958.2008.06449.x     Document Type: Article

References (33)

1. Amann, E., Ochs, B. Abel, K.J. (1988) Tightly regulated tac promoter vectors useful for the expression of unfused and fused proteins in Escherichia coli. Gene 69 : 301 315.
2. Breiding-Mack, S. Zeeck, A. (1987) Secondary metabolites by chemical screening. I. Calcium 3-hydroxyquinoline-2-carboxylate from a Streptomyces. J Antibiot (Tokyo) 40 : 953 960.
3. Datsenko, K.A. Wanner, B.L. (2000) One-step inactivation of chromosomal genes in Escherichia coli K-12 using PCR products. Proc Natl Acad Sci USA 97 : 6640 6645.
4. Feng, L., Senchenkova, S.N., Yang, J., Shashkov, A.S., Tao, J., Guo, H., et al. (2004) Synthesis of the heteropolysaccharide O antigen of Escherichia coli O52 requires an ABC transporter: structural and genetic evidence. J Bacteriol 186 : 4510 4519.
5. Fischer, C., Lipata, F. Rohr, J. (2003) The complete gene cluster of the antitumor agent gilvocarcin V and its implication for the biosynthesis of the gilvocarcins. J Am Chem Soc 125 : 7818 7819.
6. Giraud, M.F., McMiken, H.J., Leonard, G.A., Messner, P., Whitfield, C. Naismith, J.H. (1999) Overexpression, purification, crystallization and preliminary structural study of dTDP-6-deoxy-L-lyxo-4-hexulose reductase (RmlD), the fourth enzyme of the dTDP-L-rhamnose synthesis pathway, from Salmonella enterica serovar Typhimurium. Acta Crystallogr D Biol Crystallogr 55 : 2043 2046.
7. Hanniffy, O.M., Shashkov, A.S., Moran, A.P., Prendergast, M.M., Senchenkova, S.N., Knirel, Y.A. Savage, A.V. (1999) Chemical structure of a polysaccharide from Campylobacter jejuni 176.83 (serotype O: 41) containing only furanose sugars. Carbohydr Res 319 : 124 132.
8. 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.
9. Jiang, F., Hellman, U., Sroga, G.E., Bergman, B. Mannervik, B. (1995) Cloning, sequencing, and regulation of the glutathione reductase gene from the cyanobacterium Anabaena PCC 7120. J Biol Chem 270 : 22882 22889.
10. Kneidinger, B., Larocque, S., Brisson, J., Cadotte, N. Lam, J.S. (2003a) 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.
11. Kneidinger, B., O'Riordan, K., Li, J., Brisson, J., Lee, J. Lam, J.S. (2003b) Three highly conserved proteins catalyse 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. Implications for the UDP-N-acetyl-l-fucosamine biosynthetic pathway. J Biol Chem 278 : 3615 3627.
12. KPO1 gene. J Biol Chem 272 : 4121 4128.
13. Lindqvist, L., Kaiser, R., Reeves, P.R. Lindberg, A.A. (1993) Purification, characterization and HPLC assay of Salmonella glucose-1-phosphate thymidylyltransferase from the cloned rfbA gene. Eur J Biochem 211 : 763 770.
14. Liu, T., Fischer, C., Beninga, C. Rohr, J. (2004) Oxidative rearrangement processes in the biosynthesis of gilvocarcin V. J Am Chem Soc 126 : 12262 12263.
15. McNally, D.J., Schoenhofen, I.C., Mulrooney, E.F., Whitfield, D.M., Vinogradov, E., Lam, J.S., et al. (2006) Identification of labile UDP-ketosugars in Helicobacter pylori, Campylobacter jejuni and Pseudomonas aeruginosa: key metabolites used to make glycan virulence factors. Chembiochem 7 : 1865 1868.
16. Marumo, K., Lindqvist, L., Verma, N., Weintraub, A., Reeves, P.R. Lindberg, A.A. (1992) Enzymatic synthesis and isolation of thymidine diphosphate-6-deoxy-D-xylo-4-hexulose and thymidine diphosphate-L-rhamnose. Production using cloned gene products and separation by HPLC. Eur J Biochem 204 : 539 545.
17. Melo, A. Glaser, L. (1968) The mechanism of 6-deoxyhexose synthesis. II. Conversion of deoxythymidine diphosphate 4-keto-6-deoxy-D-glucose to deoxythymidine diphosphate 1-rhamnose. J Biol Chem 243 : 1475 1478.
18. Melo, A., Elliott, W.H. Glaser, L. (1968) The mechanism of 6-deoxyhexose synthesis. I. Intramolecular hydrogen transfer catalyzed by deoxythymidine diphosphate D-glucose oxidoreductase. J Biol Chem 243 : 1467 1474.
19. Nakano, Y., Suzuki, N., Yoshida, Y., Nezu, T., Yamashita, Y. Koga, T. (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.
20. Nassau, P.M., Martin, S.L., Brown, R.E., Weston, A., Monsey, D., Mcneil, M.R. Duncan, K. (1996) Galactofuranose biosynthesis in Escherichia coli K-12: identification and cloning of UDP-galactopyranose mutase. J Bacteriol 178 : 1047 1052.
21. Obhi, R.K. Creuzenet, C. (2005) Biochemical characterization of the Campylobacter jejuni Cj1294, a novel UDP-4-keto-6-deoxy-GlcNAc aminotransferase that generates UDP-4-amino-4,6-dideoxy-GalNAc. J Biol Chem 280 : 20902 20908.
22. Pfoestl, A., Hofinger, A., Kosma, P. Messner, P. (2003) Biosynthesis of dTDP-3-acetamido-3,6-dideoxy-alpha-D-galactose in Aneurinibacillus thermoaerophilus L420-91T. J Biol Chem 278 : 26410 26417.
23. Pföstl, A., Zayni, S., Hofinger, A., Kosma, P., Schäffer, C. Messner, P. (2008) Biosynthesis of dTDP-3-acetamido-3,6-dideoxy-alpha-D-glucose. Biochem J 410 : 187 194.
24. Sato, N., Nakazawa, F., Ito, T., Hoshino, T. Hoshino, E. (2003) The structure of the antigenic polysaccharide produced by Eubactrium saburreum T15. Carbohydr Res 338 : 923 930.
25. Senchenkova, S.N., Feng, L., Wang, Q., Perepelov, A.V., Qin, D., Shevelev, S.D., et al. (2006) Structural and genetic characterization of Shigella boydii type 17 O antigen and confirmation of two new genes involved in the synthesis of glucolactilic acid. Biochem Biophys Res Commun 349 : 289 295.
26. Vijayakumar, S., Merkx-Jacques, A., Ratnayake, D.B., Gryski, I., Obhi, R.K., Houle, S., et al. (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.
27. Wang, L. Reeves, P.R. (1994) Involvement of the galactosyl-1-phosphate transferase encoded by the Salmonella enterica rfbP gene in O-antigen subunit processing. J Bacteriol 176 : 4348 4356.
28. Wang, Y., Xu, Y., Perepelov, A.V., Qi, Y., Knirel, Y.A., Wang, L. Feng, L. (2007) Biochemical characterization of dTDP-D-Qui4N and dTDP-D-Qui4NAc biosynthetic pathways in Shigella dysenteriae type 7 and Escherichia coli O7. J Bacteriol 189 : 8626 8635.
29. Wierenga, R.K., Drenth, J. Schulz, G.E. (1983) Comparison of the three-dimensional protein and nucleotide structure of the FAD-binding domain of p-hydroxybenzoate hydroxylase with the FAD- as well as NADPH-binding domains of glutathione reductase. J Mol Biol 167 : 725 739.
30. Yoshida, Y., Nakano, Y., Nezu, T., Yamashita, Y. Koga, T. (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.
31. Yu, D., Ellis, H.M., Lee, E.C., Jenkins, N.A., Copeland, N.G. Court, D.L. (2000) An efficient recombination system for chromosome engineering in Escherichia coli. Proc Natl Acad Sci USA 91 : 5978 5983.
32. Zdorovenko, E.L., Ovod, V.V., Zatonsky, G.V., Shashkov, A.S., Kocharova, N.A. Knirel, Y.A. (2001) Location of the O-methyl groups in the O polysaccharide of Pseudomonas syringae pv. Phaseolicola. Carbohydr Res 330 : 505 510.
33. Zhang, Q, and Liu, H. (2000) Studies of UDP-galactopyranose mutase from Escherichia coli: an unusual role of reduced FAD in its catalysis. J Am Chem Soc 122 : 9065 9070.