Biocatalytic production of 3′-sialyllactose by use of a modified sialidase with superior trans-sialidase activity

Process Biochemistry

Volumn 49, Issue 2, 2014, Pages 265-270

  Michalak, Malwina ^a   Larsen, Dorte M ^a   Jers, Carsten ^a   Almeida, João R M ^a,c   Willer, Martin ^a,d   Li, Haiying ^b   Kirpekar, Finn ^b   Kjærulff, Louise ^a   Gotfredsen, Charlotte H ^a   Nordvang, Rune T ^a   Meyer, Anne S ^a   Mikkelsen, Jørn D ^a  

^a TECHNICAL UNIVERSITY OF DENMARK   (Denmark)

^b UNIVERSITY OF SOUTHERN DENMARK   (Denmark)

^c Parque Estação Biológica PqEB ^*  (Brazil)

^d NOVO NORDISK A S   (Denmark)

Author keywords

3 Sialyllactose; Human milk oligosaccharides; trans Sialylation; Trypanosoma rangeli

Indexed keywords

EID: 84895069393     PISSN: 13595113     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.procbio.2013.10.023     Document Type: Article

References (36)

1. L. Bode Human milk oligosaccharides: every baby needs a sugar mama Glycobiology 22 2012 1147 1162
2. C. Kunz, S. Rudloff, W.N. Klein, and S. Strobel Oligosaccharides in human milk: structural, functional and metabolic aspects Ann Rev Nutr 20 2000 699 722
3. A.L. Morrow, G.M. Ruiz-Palacios, X. Jiang, and D.S. Newburg Human milk glycans that inhibit pathogen binding protect breast-feeding infants against infectious diarrhoea J Nutr 135 2005 1304 1307
4. R.E. Ward, M. Ninonuevo, D.A. Mills, C.B. Lebrilla, and J.B. German In vitro fermentation of breast milk oligosaccharides by Bifidobacterium infantis and Lactobacillus gasseri Appl Environ Microbiol 72 2006 4497 4499
5. M.R. Ninonuevo, Y. Park, H. Yin, J. Zhang, R.E. Ward, and B.H. Clowers et al. A strategy for annotating the human milk glycome J Agric Food Chem 54 2006 7471 7480
6. D.A. Sela, J. Chapman, A. Adeuya, J.H. Kim, F. Chen, and T.R. Whitehead et al. The genome sequence of Bifidobacterium longum subsp. infantis reveals adaptations for milk utilization within the infant microbiome Proc Natl Acad Sci 105 2008 18964 18969
7. M. Kiyohara, K. Tanigawa, T. Chaiwangsri, T. Katayama, H. Ashida, and K. Yamamoto An exo-α-sialidase from bifidobacteria involved in the degradation of sialyloligosaccharides in human milk and intestinal glycoconjugates Glycobiology 21 2011 437 447
8. S. Singh, M. Scigelova, M.L. Hallberg, O.W. Howarth, S. Schenkman, and D.H.G. Crout Synthesis of sialyloligosaccharides using the trans-sialidase from Trypanosoma cruzi: novel branched and di-sialylated products from digalactoside acceptors Chem Commun 101 2000 1013 1014
9. S.P. Schenkman, and D. Eichinger Trypanosoma cruzi trans-sialidase and cell invasion Parasitol Today 9 1993 218 222
10. S. Schenkman, L.B. Chaves, L.C.P. de Carvalho, and D. Eichinger A proteolytic fragment of Trypanosoma cruzi trans-sialidase lacking the carboxyl-terminal domain is active, monomeric, and generates antibodies that inhibit enzymatic activity J Biol Chem 269 1994 7970 7975
11. A. Buschiazzo, A.C.C. Frasch, and O. Campetella Medium scale production and purification to homogeneity of a recombinant trans-sialidase from Trypanosoma cruzi Cell Mol Biol 42 1996 703 710
12. R. Agustí, G. París, L. Ratier, A.C.C. Frasch, and R.M. de Lederkremer Lactose derivatives are inhibitors of Trypanosoma cruzi trans-sialidase activity toward conventional substrates in vitro and in vivo Glycobiology 14 2004 659 670
13. V.M. Mendoza, R. Agusti, C. Gallo-Rodriguez, and R.M. de Lederkremer Synthesis of the O-linked pentasaccharide in glycoproteins of Trypanosoma cruzi and selective sialylation by recombinant trans-sialidase Carbohydr Res 341 2006 1488 1497
14. Pelletier M, Barker WA, Hakes DJ, Zopf DA. Methods for producing sialyloligosaccharides in a dairy source. US patent Nov. 27. 2001. US 6,323,008 B1.
15. McJarrow P, Garman J, Harvey S, Van Amelsfort A. Dairy process and product. International patent June19. 2003. WO 03/049547 A2.
16. M.E. Pereira, K. Zhang, Y. Gong, E.M. Herrera, and M. Ming Invasive phenotype of Trypanosoma cruzi restricted to a population expressing trans-sialidase Infect Immun 64 1996 3884 3892
17. G. París, L. Ratier, M.F. Amaya, T. Nguyen, P.M. Alzari, and A.C.C. Frasch A sialidase mutant displaying trans-sialidase activity J Mol Biol 345 2005 923 934
18. I.R. Silva, D.M. Larsen, A.S. Meyer, and J.D. Mikkelsen Identification, expression, and characterization of a novel bacterial RGI lyase enzyme for the production of bio-functional fibers Enzyme Microb Technol 49 2011 160 166
19. M. Michalak, L.V. Thomassen, H. Roytio, A.C. Ouwehand, A.S. Meyer, and J.D. Mikkelsen Expression and characterization of an endo-1,4-β-galactanase from Emericella nidulans in Pichia pastoris for enzymatic design of potentially prebiotic oligosaccharides from potato galactans Enzyme Microb Technol 50 2012 121 129
20. C. Kunz, S. Rudloff, A. Hintelmann, G. Pohlentz, and H. Egge High-pH anion-exchange chromatography with pulsed amperometric detection and molar response factors of human milk oligosaccharides J Chromatogr B 685 1996 211 221
21. C. Gustafsson, S. Govindarajan, and J. Minshull Codon bias and heterologous protein expression Trends Biotechnol 22 2004 346 353
22. K. De Schutter, Y-C. Lin, P. Tiels, A. Van Hecke, S. Glinka, and J. Weber-Lehmann et al. Genome sequence of the recombinant protein production host Pichia pastoris Nat Biotechnol 27 2009 561 566
23. T. Saito, and T. Itoh Variations and distributions of O-glycosidically linked sugar chains in bovine κ-casein J Diary Sci 75 1992 1768 1774
24. L.R. Ruhaak, A.M. Deelder, and M. Wuhrer Oligosaccharide analysis by graphitized carbon liquid chromatography-mass spectrometry Anal Bioanal Chem 394 2009 163 174
25. 13C NMR spectroscopy J Am Chem Soc 108 1986 2068 2080
26. 1H-NMR spectroscopy Carbohydr Res 191 1989 191 207
27. H. Egge, and J. Peter-Katalinic Fast atom bombardment mass spectrometry for structural elucidation of glycoconjugates Mass Spectrom Rev 6 1987 331 393
28. W. Laroy, and R. Contreras Cloning of Trypanosoma cruzi trans-sialidase and expression in Pichia pastoris Protein Expres Purif 20 2000 389 393
29. S.G. Lee, D.H. Shin, and B.G. Kim Production of sialyloligosaccharides by trans-sialidase catalyzed reaction using fetuin as a sialic acid donor Enzyme Microb Technol 31 2002 742 746
30. M.G. Gänzle Enzymatic synthesis of galacto-oligosaccharides and other lactose derivatives (hetero-oligosaccharides) from lactose Int Dairy J 22 2012 116 122
31. A. Gosling, G.W. Stevens, A.R. Barber, S.E. Kentish, and S.L. Gras Effect of the substrate concentration and water activity on the yield and rate of the transfer reaction of β-galactosidase from Bacillus circulans J Agric Food Chem 59 2011 3366 3372
32. R. Agustí, M.E. Giorgi, V.M. Mendoza, C. Gallo-Rodriguez, and R.M. de Lederkremer Comparative rates of sialylation by recombinant trans-sialidase and inhibitor properties of synthetic oligosaccharides from Trypanosoma cruzi mucins-containing galactofuranose and galactopyranose Bioorg Med Chem 15 2007 2611 2616
33. T. Palai, and P.K. Bhattacharya Kinetics of lactose conversion to galacto-oligosaccharides by β-galactosidase immobilized on PVDF membrane J Biosci Bioeng 115 2013 668 673
34. B. Rodriguez-Colinas, A. Poveda, J. Jimenez-Barbero, A.O. Ballesteros, and F.J. Plou Galacto-oligosaccharide synthesis from lactose solution or skim milk using the β-galactosidase from Bacillus circulans J Agric Food Chem 60 2012 6391 6398
35. Brunstedt J, Sørensen JF, Mikkelsen JD, Cervin MA. Lipid acyltransferase proteins and methods of making them. International patent. WO 2011/045629 A1.
36. D. Goffin, B. Wathelet, C. Blecker, C. Deroanne, Y. Malendier, and M. Paquot Comparison of the glucooligosaccharide profiles produced from maltose by two different transglucosidases from Aspergillus niger Biotechnol Agron Soc Environ 14 2010 607 616