Synthesis of novel fructooligosaccharides by substrate and enzyme engineering

Journal of Biotechnology

Volumn 138, Issue 1-2, 2008, Pages 33-41

  Beine, Rafael ^a   Moraru, Roxana ^a   Nimtz, Manfred ^b   Na'amnieh, Shukrallah ^c   Pawlowski, Alice ^c   Buchholz, Klaus ^a   Seibel, Jürgen ^a,b  

^a TECHNICAL UNIVERSITY OF BRAUNSCHWEIG   (Germany)

^b HELMHOLTZ CENTRE FOR INFECTION RESEARCH   (Germany)

^c X Zyme GmbH   (Germany)

Author keywords

Enzyme engineering; Kestose analogue; Levansucrase; Oligosaccharides

Indexed keywords

ABS RESINS; BACTERIOLOGY; BIOPOLYMERS; ENZYMES; OLIGOSACCHARIDES; POLYMERS; POLYSACCHARIDES; SUGAR (SUCROSE);

BACILLUS SUBTILIS; BENEFICIAL EFFECTS; BIOCHEMICAL PROPERTIES; DIRECT SYNTHESIS; ENZYME ENGINEERING; FRUCTAN; FRUCTO-OLIGOSACCHARIDES; KESTOSE; KESTOSE ANALOGUE; LEVANSUCRASE; NEW CLASS; PREBIOTIC; PREBIOTICS; RANDOM MUTAGENESIS; SYNTHESIS OF;

COMPLEXATION;

6 KESTOSE DERIVATIVE; FRUCTOSE OLIGOSACCHARIDE; GALACTOPOLYFRUCTOSIDE; GALACTOSE; LEVANSUCRASE; UNCLASSIFIED DRUG; XYLOOLIGOFRUCTOSIDE; XYLOSE;

ARTICLE; BACILLUS SUBTILIS; CARBOHYDRATE SYNTHESIS; ELECTROSPRAY MASS SPECTROMETRY; ENZYME ENGINEERING; ENZYME KINETICS; ENZYME SUBSTRATE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROLYSIS; METHYLATION; NONHUMAN; PRIORITY JOURNAL;

BACILLUS SUBTILIS; ESCHERICHIA COLI; GENETIC ENGINEERING; HEXOSYLTRANSFERASES; OLIGOSACCHARIDES; SUBSTRATE SPECIFICITY;

BACILLUS SUBTILIS;

EID: 53549113318     PISSN: 01681656     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jbiotec.2008.07.1998     Document Type: Article

References (32)

1. Anumula K.R., and Taylor P.B. A comprehensive procedure for preparation of partially methylated alditol acetates from glycoprotein carbohydrates. Anal. Biochem. 203 (1992) 101-108
2. Avigad G., Feingold D.S., and Hestrin S. Enzymatic synthesis and reactions of a sucrose isomer α-d-galactopyranosyl-β-d-fructofuranoside. J. Biol. Chem. 224 (1957) 295-307
3. Baciu I.E., Jördening H.J., Seibel J., and Buchholz K. Investigations of the transfructosylation reaction by fructosyltransferase from B. subtilis NCIMB 11871 for the synthesis of the sucrose analogue galactosyl-fructoside. J. Biotechnol. 116 (2005) 347-357
4. Biedendieck R., Beine R., Gamer M., Jordan E., Buchholz K., Seibel J., Dijkhuizen L., Malten M., and Jahn D. Export, purification, and activities of affinity tagged Lactobacillus reuteri levansucrase produced by Bacillus megaterium. Appl. Microbiol. Biotechnol. 74 (2007) 1062-1073
5. Boehm G., Stahl B., Jelinek J., Knol J., Miniello V., and Moro G.E. Prebiotic carbohydrates in human milk and formulas. Acta Paediatr. Suppl. 94 (2005) 18-21
6. Chambert R., and Gonzy-Treboul G. Levansucrase of Bacillus subtilis Characterization of a stabilized fructosyl-enzyme complex and identification of an aspartly residue as the binding site of the fructosyl group. Eur. J. Biochem. 71 (1976) 493-508
7. Chambert R., and Gonzy-Treboul G. Levansucrase of Bacillus subtilis: kinetic and thermodynamic aspects of transfructosylation processes. Eur. J. Biochem. 62 (1976) 55-64
8. Chambert R., and Petit-Glatron M.F. Polymerase and hydrolase activities of Bacillus subtilis levansucrase can be separately modulated by site-directed mutagenesis. Biochem. J. 279 (1991) 35-41
9. Chambert R., Treboule G., and Dedonder R. Kinetic studies of levansucrase of Bacillus subtilis. Eur. J. Biochem. 41 (1974) 285-300
10. Cheetham P.S.J., Hacking A.J., and Vlitos M. Synthesis of novel disaccharides by a newly isolated fructosyltransferase from Bacillus subtilis. Enzyme Microb. Technol. 11 (1989) 212-219
11. Eggleston G., and Cote G.L. Oligosaccharides in Food and Agriculture (2003), ACS Publications, Washington, DC
12. Henrissat B. A classification of glycosyl hydrolases based on amino acid sequence similarities. Biochem. J. 280 Pt 2 (1991) 309-316
13. Hiramaya M., Nishizawa K., and Hidaka H. Production and characteristics of fructo-oligosaccharides. In: Fuchs A. (Ed). Inulin and Inulin-Containing Crops (1993), Elsevier Publishingx Amsterdam, The Netherlands 347-354
14. Homann A., Biedendieck R., Götze S., Jahn D., and Seibel J. Insights into polymer versus oligosaccharide synthesis: mutagenesis and mechanistic studies of a novel levansucrase from Bacillus megaterium. Biochem. J. 407 (2007) 189-198
15. Hsu C.K., Liao J.W., Chung Y.C., Hsieh C.P., and Chan Y.C. Xylooligosaccharides and fructooligosaccharides affect the intestinal microbiota and precancerous colonic lesion development in rats. J. Nutr. 134 (2004) 1523-1528
16. Mäntsälä P., and Puntala M. Comparison of levansucrase from Bacillus subtilis and from Bacillus amyloliquefaciens. FEMS Microbiol. Lett. 13 (1982) 395-399
17. Meng G., and Fütterer K. Structural framework of fructosyl transfer in Bacillus subtilis levansucrase. Nat. Struct. Biol. 10 (2003) 935-941
18. Meng G., and Fütterer K. Donor substrate recognition in the raffinose-bound E342A mutant of fructosyltransferase Bacillus subtilis levansucrase. BMC Struct. Biol. 8 (2008) 16
19. Olivares-Illana V., Lopez-Munguia A., and Olvera C. Molecular characterization of inulosucrase from Leuconostoc citreum: a fructosyltransferase within a glucosyltransferase. J. Bacteriol. 185 (2003) 3606-3612
20. Ozimek L.K., van Hijum S.A., van Koningsveld G.A., van Der Maarel M.J., van Geel-Schutten G.H., and Dijkhuizen L. Site-directed mutagenesis study of the three catalytic residues of the fructosyltransferases of Lactobacillus reuteri 121. FEBS Lett. 560 (2004) 131-133
21. Ozimek L.K., Kralj S., Kaper T., van der Maarel M.J., and Dijkhuizen L. Single amino acid residue changes in subsite-1 of inulosucrase from Lactobacillus reuteri 121 strongly influence the size of products synthesized. FEBS J. 273 (2006) 4104-4113
22. Ozimek L.K., Kralj S., van der Maarel M.J., and Dijkhuizen L. The levansucrase and inulosucrase enzymes of Lactobacillus reuteri 121 catalyse processive and non-processive transglycosylation reactions. Microbiology 152 (2006) 1187-1196
23. Salminen S., Isolauri E., and Salminen E. Clinical uses of probiotics for stabilizing the gut mucosal barrier: successful strains and future challenges. Antonie Van Leeuwenhoek 70 (1996) 347-358
24. Sambrook J., Fritsch E.F., and Maniatis T. Molecular Cloning: A Laboratory Manual. 2nd ed. (1989), Cold Spring Harbor Laboratory Press, Cold Spring Harbor, New York
25. Seibel J., Moraru R., and Götze S. Biocatalytic and chemical investigations in the synthesis of sucrose analogues. Tetrahedron 61 (2005) 7081-7086
26. Seibel J., Beine R., Moraru R., Behringer C., and Buchholz K. A new pathway for the synthesis of oligosaccharides by the use of non-Leloir glycosyltransferases. Biocatal. Biotransform. 24 (2006) 157-165
27. Seibel J., Buchholz K., and Jördening H.J. Glycosylation with activated sugars using glycosyltransferases and transglycosidases. Biocatal. Biotransform. 24 (2006) 311-342
28. Seibel J., Moraru R., Götze S., Buchholz K., Na'amnieh S., Pawlowski A., and Hecht H.J. Synthesis of sucrose analogues and the mechanism of action of Bacillus subtilis fructosyltransferase (levansucrase). Carbohydr. Res. 341 (2006) 2335-2349
29. van Hijum S.A., van der Maarel M.J., and Dijkhuizen L. Kinetic properties of an inulosucrase from Lactobacillus reuteri 121. FEBS Lett. 534 (2003) 207-210
30. Varki A. Biological roles of oligosaccharides: all of the theories are correct. Glycobiology 3 (1993) 97-130
31. Wong C.H. Protein glycosylation: new challenges and opportunities. J. Org. Chem. 70 (2005) 4219-4225
32. Zuccaro A., Götze S., Kneip S., Dersch P., and Seibel J. Tailor-made fructooligosaccharides by a combination of substrate and genetic engineering. Chembiochem 9 (2008) 143-149