Kinetic examination and simulation of GDP-β-L-fucose synthetase reaction using NADPH or NADH

Biocatalysis and Biotransformation

Volumn 22, Issue 1, 2004, Pages 49-56

  Rentmeister, Andrea ^b   Hoh, Christoph ^a   Weidner, Stefan ^c   Dräger, Gerald ^d   Elling, Lothar ^e   Liese, Andreas ^f   Wandrey, Christian ^a  

^a FORSCHUNGSZENTRUM JÜLICH   (Germany)

^b UNIVERSITY OF BONN   (Germany)

^c Bachem Holding AG   (Switzerland)

^d LEIBNIZ UNIVERSITY HANNOVER   (Germany)

^e RWTH AACHEN UNIVERSITY   (Germany)

^f UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

Enzymatic synthesis; GDP D mannose 4,6 dehydratase; GDP L fucose synthethase; GDP 4 keto 6 deoxy D mannose; Kinetic examination and simulation; Nicotinamide cofactors

Indexed keywords

COMPUTER SIMULATION; ENZYME KINETICS; ENZYMES; HYDRATES; KETONES; PARAMETER ESTIMATION;

BATCH REACTIONS; KINETIC EXAMINATION;

BIOCATALYSTS;

CARBON 13; FUCOSYLTRANSFERASE; GUANOSINE DIPHOSPHATE FUCOSE; GUANOSINE DIPHOSPHATE MANNOSE; OXIDOREDUCTASE; PROTON; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE;

AQUEOUS SOLUTION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL PARAMETERS; CONTROLLED STUDY; ENZYME ACTIVITY; ENZYME ANALYSIS; ENZYME KINETICS; ENZYME MECHANISM; ENZYME PURIFICATION; ENZYME SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 1842588372     PISSN: 10242422     EISSN: None     Source Type: Journal    
DOI: 10.1080/10242420410001666362     Document Type: Article

References (44)

1. Albermann, C., Distler, J. and Piepersberg, W. (2000) "Preparative synthesis of GDP-β-L-fucose by recombinant enzymes from enterobacterial sources", Glycobiology 10, 875-881.
2. Amann, S., Dräger, G., Rupprath, C., Kirschning, A. and Elling, L. (2001) "(Chemo)enzymatic synthesis of dTDP-activated 2,6-dideoxysugars as building blocks of polyketide antibiotics", Carbohydr. Res. 335, 23-32.
3. Andrianopoulos, K., Wang, L. and Reeves, P. R. (1998) "Identification of the fucose synthetase gene in the colanic acid gene cluster of Escherichia coli K-12", J. Bacteriol. 180, 998-1001.
4. Augé, C., Malleron, A., Tahrat, H., Marc, A., Goergen, J.-L., Cerutti, M., Steelant, W. F. A., Delannoy, P. and Lubineau, A. (2000) "Outstanding stability of immobilized recombinant α(1-3/4) fucosyltransferases exploited in the synthesis of Lewis a and Lewis x trisaccharides", Chem. Comm., 2017-2018.
5. Bonin, C. P., Potter, I., Vanzin, G. F. and Reiter, W.-D. (1997) "The MUR1 gene of Arabidopsis thaliana encodes an isoform of GDP-D-mannose-4,6-dehydratase, catalyzing the first step in the de novo synthesis of GDP-L-fucose", Proc. Natl. Acad. Sci. USA 94, 2085-2090.
6. Brockhausen, I., Schutzbach, J. and Kuhns, W. (1998) "Glycoproteins and their relationship to human disease", Acta Anat. 161, 36-78.
7. Broschat, K. O., Chang, S. and Serif, G. (1985) "Purification and characterization of GDP-D-mannose 4,6-dehydratase from porcine thyroid", Eur. J. Biochem. 153, 397-401.
8. Buchholz, A., Greiner, L., Hoh, C. and Liese, A. (2002) "Genetic algorithms as a tool for capillary electrophoresis method development", J. Capillary Electrophor. Microchip Technol. 7, 51-60.
9. Chang, S., Duerr, B. and Serif, G. (1988) "An epimerase-reductase in L-fucose synthesis", J. Biol. Chem. 263, 1693-1697.
10. de Vries, T., Knegtel, R. M. A., Holmes, E. H. and Macher, B. A. (2001) "Fucosyltransferases: structure/function studies", Glycobiol 11, 119R-128R.
11. Dudziak, G., Fey, S., Hasbach, L. and Kragl, U. (1999) "Nanofiltration for purification of nucleotide sugars", J. Carbohydrate Chemistry 18, 41-49.
12. Dumon, C., Priem, B., Martin, S. L., Heyraud, A., Bosso, C. and Samain, E. (2001) "In vivo fucosylation of lacto-N-neotetraose and lacto-N-neohexaose by heterologous expression of Helicobacter pylori α1,3-fucosyltransferase in engineered Escherichia coli", Glycoconj. J. 18, 465-474.
13. Feizi, T. (1985) "Demonstration by monoclonal antibodies that carbohydrate structures of glycoproteins and glycolipids are oncodevelopmental antigens", Nature 314, 53-57.
14. Ginsburg, V. (1961) "Studies on the biosynthesis of guanosine diphosphate L-fucose", J. Biol. Chem. 236, 2389-2393.
15. Gokhale, U. B. and Hindsgaul, O. (1990) "Chemical synthesis of GDP-fucose analogs and their utilization by the Lewis α(1-4) fucosyltransferase", Can. J. Chem. 68, 1063-1070.
16. Ichikawa, Y., Look, G. L. and Wong, C. H. (1992) "Enzyme-catalyzed oligosaccharides synthesis", Anal. Biochem. 202, 215-238.
17. Idikio, H. A. (1997) "Sialyl-lewis-X, Gleason grade and stage in non-metastatic human prostate cancer", Glycoconj. J. 14, 875-877.
18. Järvinen, N., Mäki, M., Räbinä, J., Roos, C., Mattila, P. and Renkonen, R. (2001) "Cloning and expression of helicobacter pylori GDP-L-fucose synthesizing enzymes (GMD and GMER) in Saccharomyces cerevisiae", Eur. J. Biochem. 268, 6458-6464.
19. Koizumi, S., Endo, T., Tabata, K., Nagano, H., Onishi, J. and Ozaki, A. (2000) "Large-scale production of GDP-fucose and Lewis X by bacterial coupling", J. Ind. Microbiol. Biotechnol. 25, 213-217.
20. Kojima, N., Handa, K., Newman, W. and Hakomori, S. I. (1992) "Inhibition of selectin-dependent tumor cell adhesion to endothelial cells and platelets by blocking O-glycosylation of these cells", Biochem. Biophys. Res. Commun. 182, 1288-1295.
21. Kornfeld, R. H. and Ginsburg, V. (1966) "Control of synthesis of guanosine 5′-diphosphate D-mannose and guanosine 5′-diphosphate L-fucose in bacteria", Biochim. Biophys. Acta 117, 79-87.
22. Kragl, U., Klein, T., Vasic-Racki, D., Kittelmann, M., Ghisalba, O. and Wandrey, C. (1996) "Reaction engineering aspects of activated sugar production-CMP-Neu5Ac as an example", Ann. N Y Acad. Sci. 799, 577-583.
23. Leloir, L. F. (1971) "Two decades of research on the biosythesis of saccharides", Science 172, 1299-1303.
24. Lis, H. and Sharon, N. (1993) "Protein glycosylation-Structural and functional aspects", Eur. J. Biochem. 218, 1-27.
25. Macher, B. A., Holmes, E. H., Swiedler, S. J., Stults, C. L. M. and Srnka, C. A. (1991) "Human α1,3 fucosyltransferases", Glycobiol 1, 577-584.
26. Mattila, P., Räbinä, J., Hortling, S., Helin, J. and Renkonen, R. (2000) "Functional expression of Escherichia coli enzymes synthesizing GDP-L-fucose from inherent GDP-D-mannose in Saccharomyces cerevisiae", Glycobiology 10, 1041-1047.
27. McEver, R. P. (1997) "Selectin-carbohydrate interactions during inflammation and metastesis", Glycoconj. J. 14, 585-591.
28. Menon, S., Stahl, M., Kumar, R., Xu, G.-Y. and Sullivan, F. (1999) "Stereochemical course and steady-state mechanism of the reaction catalyzed by the GDP-fucose synthetase from Escherichia coli", J. Biol. Chem. 274, 26743-26750.
29. Nickel, M., Ramm, M., Wolfender, J.-L., Hostettmann, K. and Hamburger, M. (2002) "International Carbohydrate Symposium (ICS) Cairns, Australia".
30. Ohyama, C., Smith, P. L., Angata, K., Fukuda, M. N., Lowe, J. B. and Fukuda, M. (1998) "Molecular cloning and expression of GDP-D-mannose-4,6-dehydratase, a key enzyme for fucose metabolism defective in Lec13 cells", J. Biol. Chem. 273, 14582-14587.
31. Paulsen, H. (1982) "Fortschritte bei der selektiven chemischen Synthese komplexer Oligosaccharide", Angew. Chem. 94, 184-201.
32. Prohaska, R. and Schenkel-Brunner, H. (1975) "A simple and efficient method for the preparation of GDP-fucose", Anal. Biochcm. 69, 536-544.
33. Rizzi, M., Tonetti, M., Vigevani, P., Sturla, L., Bisso, A., De Flora, A., Bordo, D. and Bolognesi, M. (1998) "GDP-4-keto-6-deoxy-D-mannose epimerase/reductase from Escherichia coli, a key enzyme in the biosynthesis of GDP-L-fucose displays the structural characteristics of the RED protein homology superfamily", Structure 6, 1453-1465.
34. Rosano, C., Bisso, A., Izzo, G., Tonetti, M., Sturla, L., De Flora, A. and Bolognesi, M. (2000) "Probing the catalytic mechanism of GDP-4-keto-6-deoxy-D-mannose epimerase/reductase by kinetic and crystallographic characterization of site-specific mutants", J. Mol. Biol. 303, 77-91.
35. Schachter, H. (1991) "Enzymes associated with glycosylation", Curr. Opin. Struct. Biol., 755-765.
36. Somers, W. S., Stahl, M. L. and Sullivan, F. X. (1998) "GDP-fucose synthetase from Escherichia coli: structure of a unique member of the short-chain dehydrogenase/reductase family that catalyzes two distinct reactions at the same active site", Structure 6, 1601-1612.
37. Staudacher, E. (1996) "α1,3-Fucosyltransferases", Trends in Glycoscience and Glycotechnology (TIGG) 8, 391-408.
38. Stein, A., Kula, M.-R., Elling, L., Verseck, S. and Klaffke, W. (1995) "Synthesis of dTDP-6-deoxy-4-ketoglucose and analogues with native and recombinant dTDP-glucose-4,6-dehydratase", Angew. Chem. Int. Ed. 34, 1748-1749.
39. Stevenson, G., Andrianopoulos, K., Hobbs, M. and Reeves, P. R. (1996) "Organization of the Escherichia coli K-12 gene cluster responsible for production of the extracellular polysaccharide colanic acid", J. Bacteriol. 178, 4885-4893.
40. Sturla, L., Bisso, A., Zanardi, D., Benatti, U., De Flora, A. and Tonetti, M. (1997) "Expression, purification and characterization of GDP-D-mannose-4,6-dehydratase from Escherichia coli", FEBS Lett. 412, 126-130.
41. Sullivan, F. X., Kumar, R., Kriz, R., Stahl, M., Xu, G.-Y., Rouse, J., Chang, X.-J., Boodhoo, A., Potvin, B. and Cumming, D. A. (1998) "Molecular cloning of human GDP-mannose-4,6-dehydratase and reconstitution of GDP-fucose biosynthesis in vitro", J. Biol. Chem. 273, 8193-8202.
42. Tonetti, M., Sturla, L., Bisso, A., Benatti, U. and De Flora, A. (1996) "Synthesis of GDP-L-fucose by the human FX protein", J. Biol. Chem. 271, 27274-27279.
43. Uchiyama, T. and Hindsgaul, O. (1996) "Per-O-trimethylsilyL-α-L-fucopyranosyl iodide: a novel glycosylating agent for terminal α-L-fucosylation", Synlett 6, 499-501.
44. Varki, A. (1997) "Selectin Ligands: Will the Real Ones Please Stand up?", J. Clin. Invest. 99, 158-162.