Recent progress on galactooligosaccharides synthesis by microbial β-galactosidase

Functional Carbohydrates: Development, Characterization, and Biomanufacture

Volumn , Issue , 2017, Pages 147-182

  Lu, Lili ^a,b   Xiao, Min ^a,b  

^a Shandong University   (China)

^b SHANDONG UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

OLIGOSACCHARIDES; SACCHARIFICATION;

GALACTO-OLIGOSACCHARIDES; GALACTOOLIGOSACCHARIDES SYNTHESIS; GALACTOSIDASES; HUMAN MILK OLIGOSACCHARIDES; MICROBIOTAS; PREBIOTICS; RECENT PROGRESS; TRACE AMOUNTS;

PROBIOTICS;

EID: 85058602144     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1201/9781315371061     Document Type: Chapter

References (151)

1. Akiyama, K., Takase, M., Horikoshi, K. and Okonogi, S. (2001). Production of galactooligosaccharides from lactose using a β-glucosidase from Thermus sp. Z-1. Bioscience, Biotechnology, and Biochemistry. 65(2), 438-441.
2. Albayrak, N. and Yang, S. T. (2002). Production of galacto-oligosaccharides from lactose by Aspergillus oryzae beta-galactosidase immobilized on cotton cloth. Biotechnology and Bioengineering. 77(1), 8-19.
3. Albrecht, S., Schols, H. A., Klarenbeek, B., Voragen, A. G. and Gruppen, H. (2010). Introducing capillary electrophoresis with laser-induced fluorescence (CE-LIF) as a potential analysis and quantification tool for galactooligosaccharides extracted from complex food matrices. Journal of Agricultural and Food Chemistry. 58(5), 2787-2794.
4. Arreola, S. L., Intanon, M., Suljic, J., Kittl, R., Pham, N. H., Kosma, P., Haltrich, D. and Nguyen, T. H. (2014). Two beta-galactosidases from the human isolate Bifidobacterium breve DSM 20213: Molecular cloning and expression, biochemical characterization and synthesis of galactooligosaccharides. PLoS One. 9(8), e104056.
5. Barboza, M., Sela, D. A., Pirim, C., Locascio, R. G., Freeman, S. L., German, J. B., Mills, D. A. and Lebrilla, C. B. (2009). Glycoprofiling bifidobacterial consumption of galacto-oligosaccharides by mass spectrometry reveals strain-specific, preferential consumption of glycans. Applied and Environmental Microbiology. 75(23), 7319-7325.
6. Barile, D. and Rastall, R. A. (2013). Human milk and related oligosaccharides as prebiotics. Current Opinion in Biotechnology. 24(2), 214-219.
7. Bartesaghi, A., Matthies, D., Banerjee, S., Merk, A. and Subramaniam, S. (2014). Structure of β-galactosidase at 3.2-Å resolution obtained by cryo-electron microscopy. Proceedings of the National Academy of Sciences. 111(32), 11709-11714.
8. Bartesaghi, A., Merk, A., Banerjee, S., Matthies, D., Wu, X., Milne, J. L. and Subramaniam, S. (2015). 2.2 Å resolution cryo-EM structure of β-galactosidase in complex with a cell-permeant inhibitor. Science. 348(6239), 1147-1151.
9. Benavente, R., Pessela, B. C., Curiel, J. A., de las Rivas, B., Munoz, R., Guisan, J. M., Mancheno, J. M., Cardelle-Cobas, A., Ruiz-Matute, A. I. and Corzo, N. (2015). Improving properties of a novel betagalactosidase from Lactobacillus plantarum by covalent immobilization. Molecules. 20(5), 7874-7889.
10. Berger, J., Lee, B. and Lacroix, C. (1995). Oligosaccharides synthesis by free and immobilized β-galactosidases from Thermus aquaticus YT-1. Biotechnology Letters. 17(10), 1077-1080.
11. Bhatia, S., Prabhu, P. N., Benefiel, A. C., Miller, M. J., Chow, J., Davis, S. R. and Gaskins, H. R. (2015). Galacto-oligosaccharides may directly enhance intestinal barrier function through the modulation of goblet cells. Molecular Nutrition and Food Research. 59(3), 566-573.
12. Bode, L. (2012). Human milk oligosaccharides: Every baby needs a sugar mama. Glycobiology. 22(9), 1147-1162.
13. Boehm, G., Stahl, B., Jelinek, J., Knol, J., Miniello, V. and Moro, G. E. (2005). Prebiotic carbohydrates in human milk and formulas. Acta Paediatrica. 94(449), 18-21.
14. Boraston, A. B., McLean, B. W., Kavoosi, M., Haynes, C. A. and Kilburn, D. G. (2002). Cellulose-binding fusion proteins. In Gupta, M. N. (ed.), Methods for Affinity-Based Separations of Enzymes and Proteins. Methods and Tools in Biosciences and Medicine. Basel: Birkhäuser, pp. 148-162.
15. Brás, N. F., Fernandes, P. A. and Ramos, M. J. (2010). QM/MM studies on the β-galactosidase catalytic mechanism: Hydrolysis and transglycosylation reactions. Journal of Chemical Theory and Computation. 6(2), 421-433.
16. Bruins, M., Strubel, M., Van Lieshout, J., Janssen, A. and Boom, R. (2003). Oligosaccharide synthesis by the hyperthermostable β-glucosidase from Pyrococcus furiosus: Kinetics and modelling. Enzyme and Microbial Technology. 33(1), 3-11.
17. Cardelle-Cobas, A., Fernández, M., Salazar, N., Martínez-Villaluenga, C., Villamiel, M., Ruas-Madiedo, P. and de los Reyes-Gavilán, C. G. (2009). Bifidogenic effect and stimulation of short chain fatty acid production in human faecal slurry cultures by oligosaccharides derived from lactose and lactulose. Journal of Dairy Research. 76(3), 317-325.
18. Catarino, I., Minhalma, M., Beal, L. L., Mateus, M. and de Pinho, M. N. (2008). Assessment of saccharide fractionation by ultrafiltration and nanofiltration. Journal of Membrane Science. 312(1-2), 34-40.
19. Chen, C. W., Ou-Yang, C. C. and Yeh, C. W. (2003). Synthesis of galactooligosaccharides and transgalactosylation modeling in reverse micelles. Enzyme and Microbial Technology. 33(4), 497-507.
20. Chen, S. X., Wei, D. Z. and Hu, Z. H. (2001). Synthesis of galactooligosaccharides in AOT/isooctane reverse micelles by beta-galactosidase. Journal of Molecular Catalysis B-Enzymatic. 16(2), 109-114.
21. Cheng, C. C., Yu, M. C., Cheng, T. C., Sheu, D. C., Duan, K. J. and Tai, W. L. (2006). Production of high-content galacto-oligosaccharide by enzyme catalysis and fermentation with Kluyveromyces marxianus. Biotechnology Letters. 28(22), 793-797.
22. Cho, Y. J., Shin, H. J. and Bucke, C. (2003). Purification and biochemical properties of a galactooligosaccharide producing beta-galactosidase from Bullera singularis. Biotechnology Letters. 25(24), 2107-2111.
23. Chockchaisawasdee, S., Athanasopoulos, V. I., Niranjan, K. and Rastall, R. A. (2005). Synthesis of galacto-oligosaccharide from lactose using β-galactosidase from Kluyveromyces lactis: Studies on batch and continuous UF membrane-fitted bioreactors. Biotechnology and Bioengineering. 89(4), 434-443.
24. Corradini, C., Cavazza, A. and Bignardi, C. (2012). High-performance anion-exchange chromatography coupled with pulsed electrochemical detection as a powerful tool to evaluate carbohydrates of food interest: Principles and applications. International Journal of Carbohydrate Chemistry. 2012, 1687-9341.
25. Cruz, R., Cruz, V. d’A., Belote, J. G., de Oliveira Khenayfes, M., Dorta, C., dos Santos Oliveira, L. H., Ardiles, E. and Galli, A. (1999). Production of transgalactosylated oligosaccharides (TOS) by galactosyltransferase activity from Penicillium simplicissimum. Bioresource Technology. 70(2), 165-171.
26. De Slegte, J. (2002). Determination of trans-galactooligosaccharides in selected food products by ion-exchange chromatography: Collaborative study. Journal of AOAC International. 85(2), 417-423.
27. Diez-Municio, M., Herrero, M., Olano, A. and Moreno, F. J. (2014). Synthesis of novel bioactive lactose-derived oligosaccharides by microbial glycoside hydrolases. Microbial Biotechnology. 7(4), 315-331.
28. Dugdale, M. L., Dymianiw, D. L., Minhas, B. K., D’Angelo, I. and Huber, R. E. (2010a). Role of Met-542 as a guide for the conformational changes of Phe-601 that occur during the reaction of β-galactosidase (Escherichia coli). Biochemistry and Cell Biology. 88(5), 861-869.
29. Dugdale, M. L., Vance, M. L., Wheatley, R. W., Driedger, M. R., Nibber, A., Tran, A. and Huber, R. E. (2010b). Importance of Arg-599 of β-galactosidase (Escherichia coli) as an anchor for the open conformations of Phe-601 and the active-site loop. Biochemistry and Cell Biology. 88(6), 969-979.
30. Dumortier, V., Montreuil, J. and Bouquelet, S. (1990). Primary structure of ten galactosides formed by transglycosylation during lactose hydrolysis by Bifidobacterium bifidum. Carbohydrate Research. 201(1), 115-123.
31. Feng, Y., Chang, X., Wang, W. and Ma, R. (2009). Separation of galacto-oligosaccharides mixture by nanofiltration. Journal of the Taiwan Institute of Chemical Engineers. 40(3), 326-332.
32. Foda, M. I. and Lopez-Leiva, M. (2000). Continuous production of oligosaccharides from whey using a membrane reactor. Process Biochemistry. 35(6), 581-587.
33. Gaur, R., Pant, H., Jain, R. and Khare, S. (2006). Galacto-oligosaccharide synthesis by immobilized Aspergillus oryzae β-galactosidase. Food Chemistry. 97(3), 426-430.
34. Ghaffari-Moghaddam, M., Yekke-Ghasemi, Z., Khajeh, M., Rakhshanipour, M. and Yasin, Y. (2014). Application of response surface methodology in enzymatic synthesis: A review. Russian Journal of Bioorganic Chemistry. 40(3), 275-285.
35. Gloster, T. M., Roberts, S., Ducros, V. M., Perugino, G., Rossi, M., Hoos, R., Moracci, M., Vasella, A. and Davies, G. J. (2004). Structural studies of the β-glycosidase from Sulfolobus solfataricus in complex with covalently and noncovalently bound inhibitors. Biochemistry. 43(20), 6101-6109.
36. Golowczyc, M., Vera, C., Santos, M., Guerrero, C., Carasi, P., Illanes, A., Gomez-Zavaglia, A. and Tymczyszyn, E. (2013). Use of whey permeate containing in situ synthesised galacto-oligosaccharides for the growth and preservation of Lactobacillus plantarum. Journal of Dairy Research. 80(3), 374-381.
37. Gosling, A., Stevens, G. W., Barber, A. R., Kentish, S. E. and Gras, S. L. (2010). Recent advances refining galactooligosaccharide production from lactose. Food Chemistry. 121(2), 307-318.
38. Goulas, A. K., Grandison, A. S. and Rastall, R. A. (2003). Fractionation of oligosaccharides by nanofiltration. Journal of the Science of Food and Agriculture. 83(7), 675-680.
39. Goulas, A. K, Tzortzis, G. and Gibson, G. R. (2007). Development of a process for the production and purification of alpha- and betagalactooligosaccharides from Bifidobacterium bifidum NCIMB 41171. International Dairy Journal. 17(6), 648-656.
40. Gulec, H. A. (2013). Immobilization of beta-galactosidase from Kluyveromyces lactis onto polymeric membrane surfaces: Effect of surface characteristics. Colloids and Surfaces B-Biointerfaces. 104, 83-90.
41. Hansson, T., Kaper, T., van der Oost, J., de Vos, W. M. and Adlercreutz, P. (2001). Improved oligosaccharide synthesis by protein engineering of beta-glucosidase CelB from hyperthermophilic Pyrococcus furiosus. Biotechnology and Bioengineering. 73(3), 203-210.
42. Hassan, N., Geiger, B., Gandini, R., Patel, B. K., Kittl, R., Haltrich, D., Nguyen, T. H., Divne, C. and Tan, T. C. (2016). Engineering a thermostable Halothermothrix orenii beta-glucosidase for improved galacto-oligosaccharide synthesis. Applied Microbiology and Biotechnology. 100(8), 3533-3543.
43. Hassan, N., Nguyen, T. H., Intanon, M., Kori, L. D., Patel, B. K., Haltrich, D., Divne, C. and Tan, T. C. (2015). Biochemical and structural characterization of a thermostable beta-glucosidase from Halothermothrix orenii for galacto-oligosaccharide synthesis. Applied Microbiology and Biotechnology. 99(4), 1731-1744.
44. Henze, M., You, D.-J., Kamerke, C., Hoffmann, N., Angkawidjaja, C., Ernst, S., Pietruszka, J., Kanaya, S. and Elling, L. (2014). Rational design of a glycosynthase by the crystal structure of β-galactosidase from Bacillus circulans (BgaC) and its use for the synthesis of N-acetyllactosamine type 1 glycan structures. Journal of Biotechnology. 191, 78-85.
45. Hernandez, O., Ruiz-Matute, A. I., Olano, A., Moreno, F. J. and Sanz, M. L. (2009). Comparison of fractionation techniques to obtain prebiotic galactooligosaccharides. International Dairy Journal. 19(9), 531-536.
46. Hidaka, M., Fushinobu, S., Ohtsu, N., Motoshima, H., Matsuzawa, H., Shoun, H. and Wakagi, T. (2002). Trimeric crystal structure of the glycoside hydrolase family 42 beta-galactosidase from Thermus thermophilus A4 and the structure of its complex with galactose. Journal of Agricultural and Food Chemistry. 322(1), 79-91.
47. Hsu, C. A., Lee, S. L. and Chou, C. C. (2007). Enzymatic production of galactooligosaccharides by beta-galactosidase from Bifidobacterium longum BCRC 15708. Journal of Agricultural and Food Chemistry. 55(6), 2225-2230.
48. Huber, R., Kurz, G. and Wallenfels, K. (1976). A quantitation of the factors which affect the hydrolase and transgalactosylase activities of β-galactosidase (E. coli) on lactose. Biochemistry. 15(9), 1994-2001.
49. Huebner, J., Wehling, R. L. and Hutkins, R. W. (2007). Functional activity of commercial prebiotics. International Dairy Journal. 17(7), 770-775.
50. Huerta, L. M., Vera, C., Guerrero, C., Wilson, L. and Illanes, A. (2011). Synthesis of galacto-oligosaccharides at very high lactose concentrations with immobilized β-galactosidases from Aspergillus oryzae. Process Biochemistry. 46(1), 245-252.
51. Hung, M.-N. and Lee, B. (2002). Purification and characterization of a recombinant β-galactosidase with transgalactosylation activity from Bifidobacterium infantis HL96. Applied Microbiology and Biotechnology. 58(4), 439-445.
52. Intanon, M., Arreola, S. L., Pham, N. H., Kneifel, W., Haltrich, D. and Nguyen, T. H. (2014). Nature and biosynthesis of galacto-oligosaccharides related to oligosaccharides in human breast milk. FEMS Microbiology Letters. 353(2), 89-97.
53. Iqbal, S., Nguyen, T. H., Nguyen, H. A., Nguyen, T. T., Maischberger, T., Kittl, R. and Haltrich, D. (2011). Characterization of a heterodimeric GH2 beta-galactosidase from Lactobacillus sakei Lb790 and formation of prebiotic galacto-oligosaccharides. Journal of Agricultural and Food Chemistry. 59(8), 3803-3811.
54. Iqbal, S., Nguyen, T. H., Nguyen, T. T., Maischberger, T. and Haltrich, D. (2010). beta-Galactosidase from Lactobacillus plantarum WCFS1: Biochemical characterization and formation of prebiotic galactooligosaccharides. Carbohydrate Research. 345(10), 1408-1416.
55. Ishikawa, K., Kataoka, M., Yanamoto, T., Nakabayashi, M., Watanabe, M., Ishihara, S. and Yamaguchi, S. (2015). Crystal structure of beta-galactosidase from Bacillus circulans ATCC 31382 (BgaD) and the construction of the thermophilic mutants. FEBS Journal. 282(13), 2540-2552.
56. Jancewicz, L. J., Wheatley, R. W., Sutendra, G., Lee, M., Fraser, M. E. and Huber, R. E. (2012). Ser-796 of β-galactosidase (Escherichia coli) plays a key role in maintaining a balance between the opened and closed conformations of the catalytically important active site loop. Archives of Biochemistry and Biophysics. 517(2), 111-122.
57. Ji, E.-S., Park, N.-H. and Oh, D.-K. (2005). Galacto-oligosaccharide production by a thermostable recombinant β-galactosidase from Thermotoga maritima. World Journal of Microbiology and Biotechnology. 21(5), 759-764.
58. Jorgensen, F., Hansen, O. C. and Stougaard, P. (2001). High-efficiency synthesis of oligosaccharides with a truncated beta-galactosidase from Bifidobacterium bifidum. Applied Microbiology and Biotechnology. 57(5-6), 647-652.
59. Jovanovic-Malinovska, R., Fernandes, P., Winkelhausen, E. and Fonseca, L. (2012). Galacto-oligosaccharides synthesis from lactose and whey by β-galactosidase immobilized in PVA. Applied Biochemistry and Biotechnology. 168(5), 1197-1211.
60. Juajun, O., Nguyen, T. H., Maischberger, T., Iqbal, S., Haltrich, D. and Yamabhai, M. (2011). Cloning, purification, and characterization of beta-galactosidase from Bacillus licheniformis DSM 13. Applied Microbiology and Biotechnology. 89(3), 645-654.
61. Juers, D. H., Heightman, T. D., Vasella, A., McCarter, J. D., Mackenzie, L., Withers, S. G. and Matthews, B. W. (2001). A structural view of the action of Escherichia coli (lacZ) beta-galactosidase. Biochemistry. 40(49), 14781-14794.
62. Juers, D. H., Jacobson, R. H., Wigley, D., Zhang, X. J., Huber, R. E., Tronrud, D. E. and Matthews, B. W. (2000). High resolution refinement of beta-galactosidase in a new crystal form reveals multiple metalbinding sites and provides a structural basis for alpha-complementation. Protein Science. 9(9), 1685-1699.
63. Keisuke, M., Tamura, N. and Watanabe, T. (1988). Method for producing galactooligosaccharide. Eur. Patent EP0272095.
64. Kim, J.-H., Lee, D.-H. and Lee, J.-S. (2001). Production of galactooligosaccharide by β-galactosidase from Kluyveromyces maxianus var lactis OE-20. Biotechnology and Bioprocess Engineering. 6(5), 337-340.
65. Lamsal, B. P. (2012). Production, health aspects and potential food uses of dairy prebiotic galactooligosaccharides. Journal of the Science of Food and Agriculture. 92(10), 2020-2028.
66. Lee, S. Y., Choi, J. H. and Xu, Z. (2003). Microbial cell-surface display. Trends in Biotechnology. 21(1), 45-52.
67. Li, L., Li, G., Cao, L. C., Ren, G. H., Kong, W., Wang, S. D., Guo, G. S. and Liu, Y. H. (2015). Characterization of the cross-linked enzyme aggregates of a novel beta-galactosidase, a potential catalyst for the synthesis of galacto-oligosaccharides. Journal of Agricultural and Food Chemistry. 63(3), 894-901.
68. Li, Y., Lu, L., Wang, H., Xu, X. and Xiao, M. (2009). Cell surface engineering of a beta-galactosidase for galactooligosaccharide synthesis. Applied and Environmental Microbiology. 75(18), 5938-5942.
69. Li, Z., Xiao, M., Lu, L. and Li, Y. (2008). Production of non-monosaccharide and high-purity galactooligosaccharides by immobilized enzyme catalysis and fermentation with immobilized yeast cells. Process Biochemistry. 43(8), 896-899.
70. Liu, H., Liu, J., Tan, B., Zhou, F., Qin, Y. and Yang, R. (2012). Covalent immobilization of Kluyveromyces fragilis beta-galactosidase on magnetic nanosized epoxy support for synthesis of galacto-oligosaccharide. Bioprocess and Biosystems Engineering. 35(8), 1287-1295.
71. Lu, L., Gu, G., Xiao, M. and Wang, F. (2010). Separation and structure analysis of trisaccharide isomers produced from lactose by Lactobacillus bulgaricus L3 β-galactosidase. Food Chemistry. 121(4), 1283-1288.
72. Lu, L., Xiao, M., Li, Z., Li, Y. and Wang, F. (2009). A novel transglycosylating β-galactosidase from Enterobacter cloacae B5. Process Biochemistry. 44(2), 232-236.
73. Lu, L., Xiao, M., Xu, X., Li, Z. and Li, Y. (2007). A novel beta-galactosidase capable of glycosyl transfer from Enterobacter agglomerans B1. Biochemical and Biophysical Research Communications. 356(1), 78-84.
74. Lu, L., Xu, S., Zhao, R., Zhang, D., Li, Z., Li, Y. and Xiao, M. (2012). Synthesis of galactooligosaccharides by CBD fusion beta-galactosidase immobilized on cellulose. Bioresource Technology. 116, 327-333.
75. Mahoney, R. R. (1998). Galactosyl-oligosaccharide formation during lactose hydrolysis: A review. Food Chemistry. 63(2), 147-154.
76. Maischberger, T., Nguyen, T. H., Sukyai, P., Kittl, R., Riva, S., Ludwig, R. and Haltrich, D. (2008). Production of lactose-free galacto-oligosaccharide mixtures: Comparison of two cellobiose dehydrogenases for the selective oxidation of lactose to lactobionic acid. Carbohydrate Research. 343(12), 2140-2147.
77. Maksimainen, M., Hakulinen, N., Kallio, J. M., Timoharju, T., Turunen, O. and Rouvinen, J. (2011). Crystal structures of Trichoderma reesei betagalactosidase reveal conformational changes in the active site. Journal of Structural Biology. 174(1), 156-163.
78. Maksimainen, M., Paavilainen, S., Hakulinen, N. and Rouvinen, J. (2012). Structural analysis, enzymatic characterization, and catalytic mechanisms of beta-galactosidase from Bacillus circulans sp. alkalophilus. FEBS Journal. 279(10), 1788-1798.
79. Martínez-Villaluenga, M., Cobas, A. C., Corzo, N., Olano, A. and Villamiel, M. (2008). Optimization of conditions for galactooligosaccharide synthesis during lactose hydrolysis by β-galactosidase from Kluyveromyces lactis (Lactozym 3000 L HP G). Food Chemistry. 107, 258-264.
80. Matella, N., Dolan, K. and Lee, Y. (2006). Comparison of galactooligosaccharide production in free-enzyme ultrafiltration and in immobilizedenzyme systems. Journal of Food Science. 71(7), C363-C368.
81. Maugard, T., Gaunt, D., Legoy, M. D. and Besson, T. (2003). Microwaveassisted synthesis of galacto-oligosaccharides from lactose with immobilized beta-galactosidase from Kluyveromyces lactis. Biotechnology Letters. 25(8), 623-629.
82. McCarter, J. D. and Withers, S. G. (1994). Mechanisms of enzymatic glycoside hydrolysis. Current Opinion in Structural Biology. 4(6), 885-892.
83. Melo, E. P., Aires-Barros, M. R. and Cabral, J. M. (2001). Reverse micelles and protein biotechnology. Biotechnology Annual Review. 7, 87-129.
84. Michelon, M., Manera, A. P., Carvalho, A. L. and Maugeri Filho, F. (2014). Concentration and purification of galacto-oligosaccharides using nanofiltration membranes. International Journal of Food Science and Technology. 49(8), 1953-1961.
85. Misson, M., Jin, B., Chen, B. and Zhang, H. (2015). Enhancing enzyme stability and metabolic functional ability of β-galactosidase through functionalized polymer nanofiber immobilization. Bioprocess and Biosystems Engineering. 38(10), 1915-1923.
86. Moravčík, J., Gramblička, M., Wiśniewski, Ł., Vaňková, K. and Polakovič, M. (2012). Influence of the ionic form of a cation-exchange adsorbent on chromatographic separation of galactooligosaccharides. Chemical Papers. 66(6), 583-588.
87. Nakakuki, T. (1993). Oligosaccharides: Production, Properties and Applications. Basel, Switzerland: Gordon and Breach, pp. 90-106.
88. Nakao, M., Harada, M., Kodama, Y., Nakayama, T., Shibano, Y. and Amachi, T. (1994). Purification and characterization of a thermostable β-galactosidase with high transgalactosylation activity from Saccharopolyspora rectivirgula. Applied Microbiology and Biotechnology. 40(5), 657-663.
89. Nakkharat, P., Kulbe, K. D., Yamabhai, M. and Haltrich, D. (2006). Formation of galacto-oligosaccharides during lactose hydrolysis by a novel beta-galactosidase from the moderately thermophilic fungus Talaromyces thermophilus. Biotechnology Journal. 1(6), 633-638.
90. Neri, D. F., Balcão, V. M., Costa, R. S., Rocha, I. C., Ferreira, E. M., Torres, D. P., Rodrigues, L. R., Carvalho, L. B. and Teixeira, J. A. (2009). Galacto-oligosaccharides production during lactose hydrolysis by free Aspergillus oryzae β-galactosidase and immobilized on magnetic polysiloxane-polyvinyl alcohol. Food Chemistry. 115(1), 92-99.
91. Newburg, D. S. (2000). Oligosaccharides in human milk and bacterial colonization. Journal of Pediatric Gastroenterology and Nutrition. 30, S8-S17.
92. Nguyen, T.-H., Splechtna, B., Krasteva, S., Kneifel, W., Kulbe, K. D., Divne, C. and Haltrich, D. (2007). Characterization and molecular cloning of a heterodimeric β-galactosidase from the probiotic strain Lactobacillus acidophilus R22. FEMS Microbiology Letters. 269(1), 136-144.
93. Nguyen, T.-T., Nguyen, H. A., Arreola, S. L., Mlynek, G., Djinović-Carugo, K., Mathiesen, G., Nguyen, T.-H. and Haltrich, D. (2012). Homodimeric β-galactosidase from Lactobacillus delbrueckii subsp. bulgaricus DSM 20081: Expression in Lactobacillus plantarum and biochemical characterization. Journal of Agricultural and Food Chemistry. 60(7), 1713-1721.
94. Niittynen, L., Kajander, K. and Korpela, R. (2007). Galacto-oligosaccharides and bowel function. Scandinavian Journal of Food and Nutrition. 51(2), 62-66.
95. Nobre, C., Santos, M. J., Dominguez, A., Torres, D., Rocha, O., Peres, A. M., Rocha, I., Ferreira, E. C., Teixeira, J. A. and Rodrigues, L. R. (2009). Comparison of adsorption equilibrium of fructose, glucose and sucrose on potassium gel-type and macroporous sodium ion-exchange resins. Analytica Chimica Acta. 654(1), 71-76.
96. Ohtsuka, K., Tanoh, A., Ozawa, O., Kanematsu, T., Uchida, T. and Shinke, R. (1990). Purification and properties of a β-galactosidase with high galactosyl transfer activity from Cryptococcus laurentii OKN-4. Journal of Fermentation and Bioengineering. 70(5), 301-307.
97. Oliveira, C., Guimarães, P. M. and Domingues, L. (2011). Recombinant microbial systems for improved β-galactosidase production and biotechnological applications. Biotechnology Advances. 29(6), 600-609.
98. Onishi, N., Kira, I. and Yokozeki, K. (1996). Galacto-oligosaccharide production from lactose by Sirobasidium magnum CBS6803. Letters in Applied Microbiology. 23(4), 253-256.
99. Onishi, N. and Tanaka, T. (1998). Galacto-oligosaccharide production using a recycling cell culture of Sterigmatomyces elviae CBS8119. Letters in Applied Microbiology. 26(2), 136-139.
100. Onishi, N., Yamashiro, A. and Yokozeki, K. (1995). Production of galactooligosaccharide from lactose by Sterigmatomyces elviae CBS8119. Applied and Environmental Microbiology. 61(11), 4022-4025.
101. Osman, A., Symeou, S., Trisse, V., Watson, K. A., Tzortzis, G. and Charalampopoulos, D. (2014). Synthesis of prebiotic galactooligosaccharides from lactose using bifidobacterial β-galactosidase (BbgIV) immobilised on DEAE-Cellulose, Q-Sepharose and amino-ethyl agarose. Biochemical Engineering Journal. 82(15), 188-199.
102. Palai, T. and Bhattacharya, P. K. (2013). Kinetics of lactose conversion to galacto-oligosaccharides by β-galactosidase immobilized on PVDF membrane. Journal of Bioscience and Bioengineering. 115(6), 668-673.
103. Palai, T., Kumar, A. and Bhattacharya, P. K. (2015). Kinetic studies and model development for the formation of galacto-oligosaccharides from lactose using synthesized thermo-responsive bioconjugate. Enzyme and Microbial Technology. 70, 42-49.
104. Pan, C., Hu, B., Li, W., Sun, Y., Ye, H. and Zeng, X. (2009). Novel and efficient method for immobilization and stabilization of β-d-galactosidase by covalent attachment onto magnetic Fe3O4-chitosan nanoparticles. Journal of Molecular Catalysis B: Enzymatic. 61(3), 208-215.
105. Panesar, P. S., Kumari, S. and Panesar, R. (2010). Potential applications of immobilized β-galactosidase in food processing industries. Enzyme Research. 2010, 473137.
106. Park, A.-R. and Oh, D.-K. (2010). Galacto-oligosaccharide production using microbial β-galactosidase: Current state and perspectives. Applied Microbiology and Biotechnology. 85(5), 1279-1286.
107. Park, H.-Y., Kim, H.-J., Lee, J.-K., Kim, D. and Oh, D.-K. (2008). Galactooligosaccharide production by a thermostable β-galactosidase from Sulfolobus solfataricus. World Journal of Microbiology and Biotechnology. 24(8), 1553-1558.
108. Pereira-Rodríguez, Á., Fernández-Leiro, R., González-Siso, M. I., Cerdán, M. E., Becerra, M. and Sanz-Aparicio, J. (2012). Structural basis of specificity in tetrameric Kluyveromyces lactis β-galactosidase. Journal of Structural Biology. 177(2), 392-401.
109. Perugino, G., Trincone, A., Rossi, M. and Moracci, M. (2004). Oligosaccharide synthesis by glycosynthases. Trends in Biotechnology. 22(1), 31-37.
110. Placier, G., Watzlawick, H., Rabiller, C. and Mattes, R. (2009). Evolved β-galactosidases from Geobacillus stearothermophilus with improved transgalactosylation yield for galacto-oligosaccharide production. Applied Environmental Microbiology. 75(19), 6312-6321.
111. Prakash, B. S., Suyama, K., Itoh, T. and Adachi, S. (1989). Structure elucidation of major galactooligosaccharides formed by growing cultures of Trichoderma harzianum. Journal of Agricultural and Food Chemistry. 37(2), 334-337.
112. Pruksasri, S., Nguyen, T. H., Haltrich, D. and Novalin, S. (2015). Fractionation of a galacto-oligosaccharides solution at low and high temperature using nanofiltration. Separation and Purification Technology. 151, 124-130.
113. Rabiu, B. A., Jay, A. J., Gibson, G. R. and Rastall, R. A. (2001). Synthesis and fermentation properties of novel galacto-oligosaccharides by β-galactosidases from Bifidobacterium species. Applied Environmental Microbiology. 67(6), 2526-2530.
114. Rodriguez-Colinas, B., Fernandez-Arrojo, L., Ballesteros, A. O. and Plou, F. J. (2014). Galactooligosaccharides formation during enzymatic hydrolysis of lactose: Towards a prebiotic-enriched milk. Food Chemistry. 145, 388-394.
115. Rodriguez-Colinas, B., Kolida, S., Baran, M., Ballesteros, A. O., Rastall, R. A. and Plou, F. J. (2013). Analysis of fermentation selectivity of purified galacto-oligosaccharides by in vitro human faecal fermentation. Applied Microbiology Biotechnology. 97(13), 5743-5752.
116. Rodriguez-Colinas, B., Poveda, A., Jimenez-Barbero, J., Ballesteros, A. O. and Plou, F. J. (2012). Galacto-oligosaccharide synthesis from lactose solution or skim milk using the β-galactosidase from Bacillus circulans. Journal of Agricultural and Food Chemistry. 60(25), 6391-6398.
117. Rojas, A., Nagem, R., Neustroev, K., Arand, M., Adamska, M., Eneyskaya, E., Kulminskaya, A., Garratt, R., Golubev, A. and Polikarpov, I. (2004). Crystal structures of β-galactosidase from Penicillium sp. and its complex with galactose. Journal of Molecular Biology. 343(5), 1281-1292.
118. Roy, D., Daoudi, L. and Azaola, A. (2002). Optimization of galactooligosaccharide production by Bifidobacterium infantis RW-8120 using response surface methodology. Journal of Industrial Microbiology and Biotechnology. 29(5), 281-285.
119. Rycroft, C., Jones, M., Gibson, G. and Rastall, R. (2001). A comparative in vitro evaluation of the fermentation properties of prebiotic oligosaccharides. Journal of Applied Microbiology. 91(5), 878-887.
120. Rye, C. S. and Withers, S. G. (2000). Glycosidase mechanisms. Current Opinion in Chemical Biology. 4(5), 573-580.
121. Sako, T., Matsumoto, K. and Tanaka, R. (1999). Recent progress on research and applications of non-digestible galacto-oligosaccharides. International Dairy Journal. 9(1), 69-80.
122. Sangwan, V., Tomar, S., Singh, R., Singh, A. and Ali, B. (2011). Galactooligosaccharides: Novel components of designer foods. Journal of Food Science. 76(4), R103-R111.
123. Searle, L. E., Best, A., Nunez, A., Salguero, F. J., Johnson, L., Weyer, U., Dugdale, A. H., Cooley, W. A., Carter, B. and Jones, G. (2009). A mixture containing galactooligosaccharide, produced by the enzymic activity of Bifidobacterium bifidum, reduces Salmonella enterica serovar Typhimurium infection in mice. Journal of Medical Microbiology. 58(1), 37-48.
124. Searle, L. E., Cooley, W. A., Jones, G., Nunez, A., Crudgington, B., Weyer, U., Dugdale, A. H., Tzortzis, G., Collins, J. W. and Woodward, M. J. (2010). Purified galactooligosaccharide, derived from a mixture produced by the enzymic activity of Bifidobacterium bifidum, reduces Salmonella enterica serovar Typhimurium adhesion and invasion in vitro and in vivo. Journal of Medical Microbiology. 59(12), 1428-1439.
125. Shigehisa, A., Sotoya, H., Sato, T., Hara, T., Matsumoto, H. and Matsuki, T. (2015). Characterization of a bifidobacterial system that utilizes galacto-oligosaccharides. Microbiology. 161(7), 1463-1470.
126. Shin, H.-J., Park, J.-M. and Yang, J.-W. (1998). Continuous production of galacto-oligosaccharides from lactose by Bullera singularis β-galactosidase immobilized in chitosan beads. Process Biochemistry. 33(8), 787-792.
127. Shin, H.-J. and Yang, J.-W. (1994). Galacto-oligosaccharide production by β-galactosidase in hydrophobic organic media. Biotechnology Letters. 16(11), 1157-1162.
128. Shoaf, K., Mulvey, G. L., Armstrong, G. D. and Hutkins, R. W. (2006). Prebiotic galactooligosaccharides reduce adherence of enteropathogenic Escherichia coli to tissue culture cells. Infection and Immunity. 74(12), 6920-6928.
129. Shoseyov O, Shani Z, Levy I. (2006). Carbohydrate binding modules: Biochemical properties and novel applications. Microbiology and Molecular Biology Reviews. 70(2), 283-295.
130. Sinclair, H. R., de Slegte, J., Gibson, G. R. and Rastall, R. A. (2009). Galactooligosaccharides (GOS) inhibit Vibrio cholerae toxin binding to its GM1 receptor. Journal of Agricultural and Food Chemistry. 57(8), 3113-3119.
131. Skálová, T., Dohnálek, J., Spiwok, V., Lipovová, P., Vondráčková, E., Petroková, H., Dušková, J., Strnad, H., Kralova, B. and Hašek, J. (2005). Cold-active β-galactosidase from Arthrobacter sp. C2-2 forms compact 660kDa hexamers: Crystal structure at 1.9 Å resolution. Journal of Molecular Biology. 353(2), 282-294.
132. Solomon, H. V., Tabachnikov, O., Feinberg, H., Govada, L., Chayen, N. E., Shoham, Y. and Shoham, G. (2013). Crystallization and preliminary crystallographic analysis of GanB, a GH42 intracellular beta-galactosidase from Geobacillus stearothermophilus. Acta Crystallographica Section F-Structural Biology Communications. 69(10), 1114-1119.
133. Splechtna, B., Nguyen, T. H. and Haltrich, D. (2007). Comparison between discontinuous and continuous lactose conversion processes for the production of prebiotic galacto-oligosaccharides using beta-galactosidase from Lactobacillus reuteri. Journal of Agricultural and Food Chemistry. 55(16), 6772-6777.
134. Splechtna, B., Nguyen, T. H., Steinbock, M., Kulbe, K. D., Lorenz, W. and Haltrich, D. (2006). Production of prebiotic galacto-oligosaccharides from lactose using beta-galactosidases from Lactobacillus reuteri. Journal of Agricultural and Food Chemistry. 54(14), 4999-5006.
135. Splechtna, B., Petzelbauer, I., Baminger, U., Haltrich, D., Kulbe, K. D. and Nidetzky, B. (2001). Production of a lactose-free galacto-oligosaccharide mixture by using selective enzymatic oxidation of lactose into lactobionic acid. Enzyme and Microbial Technology. 29(6-7), 434-440.
136. Srivastava, A., Mishra, S. and Chand, S. (2015). Transgalactosylation of lactose for synthesis of galacto-oligosaccharides using Kluyveromyces marxianus NCIM 3551. New Biotechnology. 32(4), 412-418.
137. Stiverson, J., Williams, T., Chen, J., Adams, S., Hustead, D., Price, P., Guerrieri, J., Deacon, J. and Yu, Z. (2014). Prebiotic oligosaccharides: Comparative evaluation using in vitro cultures of infants’ fecal microbiomes. Applied and Environmental Microbiology. 80(23), 7388-7397.
138. Torres, D. P. M., Goncalves, M. P., Teixeira, J. A. and Rodrigues, L. R. (2010). Galacto-oligosaccharides: Production, properties, applications, and significance as prebiotics. Comprehensive Reviews in Food Science and Food Safety. 9(5), 438-454.
139. Tzortzis, G., Goulas, A. K., Gee, J. M. and Gibson, G. R. (2005a). A novel galactooligosaccharide mixture increases the bifidobacterial population numbers in a continuous in vitro fermentation system and in the proximal colonic contents of pigs in vivo. Journal of Nutrition. 135(7), 1726-1731.
140. Tzortzis, G., Goulas, A. K. and Gibson, G. R. (2005b). Synthesis of prebiotic galactooligosaccharides using whole cells of a novel strain, Bifidobacterium bifidum NCIMB 41171. Applied Microbiology and Biotechnology. 68(3), 412-416.
141. Tzortzis, G. and Vulevic, J. (2009). Galacto-oligosaccharide prebiotics. In D. Charalampopoulos and R. A. Rastall (eds.), Prebiotics and Probiotics Science and Technology. New York: Springer, pp. 207-244.
142. Urrutia, P., Bernal, C., Wilson, L. and Illanes, A. s. (2014). Improvement of chitosan derivatization for the immobilization of Bacillus circulans β-galactosidase and its further application in galacto-oligosaccharide synthesis. Journal of Agricultural and Food Chemistry. 62(41), 10126-10135.
143. van Leeuwen, S. S., Kuipers, B. J., Dijkhuizen, L. and Kamerling, J. P. (2014a). 1H NMR analysis of the lactose/β-galactosidase-derived galacto-oligosaccharide components of Vivinal® GOS up to DP5. Carbohydrate Research. 400, 59-73.
144. van Leeuwen, S. S., Kuipers, B. J., Dijkhuizen, L. and Kamerling, J. P. (2014b). Development of a 1H NMR structural-reporter-group concept for the analysis of prebiotic galacto-oligosaccharides of the [β-d-Galp-(1→x)] n-d-Glcp type. Carbohydrate Research. 400, 54-58.
145. Wang, K., Lu, Y., Liang, W. Q., Wang, S. D., Jiang, Y., Huang, R. and Liu, Y. H. (2012). Enzymatic synthesis of galacto-oligosaccharides in an organic-aqueous biphasic system by a novel beta-galactosidase from a metagenomic library. Journal of Agricultural and Food Chemistry. 60(15), 3940-3946.
146. Wheatley, R. W., Kappelhoff, J. C., Hahn, J. N., Dugdale, M. L., Dutkoski, M. J., Tamman, S. D., Fraser, M. E. and Huber, R. E. (2012). Substitution for Asn460 cripples beta-galactosidase (Escherichia coli) by increasing substrate affinity and decreasing transition state stability. Journal of Agricultural and Food Chemistry. 521(1-2), 51-61.
147. Wheatley, R. W., Lo, S., Jancewicz, L. J., Dugdale, M. L. and Huber, R. E. (2013). Structural explanation for allolactose (lac operon inducer) synthesis by lacZ β-galactosidase and the evolutionary relationship between allolactose synthesis and the lac repressor. Journal of Biological Chemistry. 288(18), 12993-13005.
148. Wu, Y., Yuan, S., Chen, S., Wu, D., Chen, J. and Wu, J. (2013). Enhancing the production of galacto-oligosaccharides by mutagenesis of Sulfolobus solfataricus beta-galactosidase. Food Chemistry. 138(2-3), 1588-1595.
149. Yanahira, S., Kobayashi, T., Suguri, T., Nakakoshi, M., Miura, S., Ishikawa, H. and Nakajima, I. (1995). Formation of oligosaccharides from lactose by Bacillus circulans beta-galactosidase. Bioscience, Biotechnology and Biochemistry. 59(6), 1021-1026.
150. Yi, S. H., Alli, I., Park, K. H. and Lee, B. (2011). Overexpression and characterization of a novel transgalactosylic and hydrolytic beta-galactosidase from a human isolate Bifidobacterium breve B24. New Biotechnology. 28(6), 806-813.
151. Yu, L. and O’Sullivan, D. (2014). Production of galactooligosaccharides using a hyperthermophilic β-galactosidase in permeabilized whole cells of Lactococcus lactis. Journal of Dairy Science. 97(2), 694-703.