Enzymatic synthesis of oligosaccharides: A powerful tool for a sweet challenge

Current Organic Chemistry

Volumn 17, Issue 7, 2013, Pages 701-718

  Filice, Marco ^a   Marciello, Marzia ^b  

^a INSTITUTO DE CATÁLISIS Y PETROLEOQUÍMICA   (Spain)

^b INSTITUTO DE CIENCIA DE MATERIALES DE MADRID   (Spain)

Author keywords

Biocatalysis; Carbohydrate; Glycoconjugate; Glycosylhydrolases; Glycosyltransferase; Glycosynthases

Indexed keywords

BIOACTIVITY; ENZYMES; SIGNAL TRANSDUCTION;

BIOCATALYSIS; CARCINOGENESES; ENZYMATIC SYNTHESIS; GLYCOCONJUGATES; GLYCOSYL TRANSFERASE; GLYCOSYLHYDROLASE; GLYCOSYNTHASE; IMMUNE RESPONSE; LIFE PROCESS; NATURAL PRODUCTS;

OLIGOSACCHARIDES;

EID: 84876734301     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/1385272811317070006     Document Type: Review

References (197)

1. Varki, A., Cummings, D. C., Esko, J. D., Freeze, H.H., Stanley, P., Bertozzi, C. R., Hart, G.W., Etzler, M.E., Essentials of Glycobiology, Cold Spring Harbor Press, New York, 2009.
2. Dwek, R.A. Glycobiology: Toward understanding the function of sugars. Chem. Rev. 1996, 96, 683-720.
3. Varki, A. Biological roles of oligosaccharides: All of the theories are correct. Glycobiology 1993, 3, 97-130.
4. Hanson, S., Best, M., Bryan, M., Wong, C.-H. Chemoenzymatic synthesis of oligosaccharides and glycoproteins. Trends Biochem. Sci., 2004, 29, 656-663.
5. Jiang, Y.; Xu, C. The calculation of information and organismal complexity. Biol. Direct 2010, 59, 1-17.
6. Varki, A. Nothing in Glycobiology Makes Sense, except in the Light of Evolution. Cell 2006, 126, 841-845.
7. Gagneux, P.; Varki, A. Evolutionary considerations in relating oligosaccharide diversity to biological function. Glycobiology 1999, 9, 747-755.
8. Bishop, J. R.; Gagneux, P. Evolution of carbohydrate antigens-Microbial forces shaping host glycomes? Glycobiology 2007, 17, 23R-34R.
9. Ohtsubo, K., Marth, J.D. Glycosylation in cellular mechanisms of health and disease. Cell 2006, 126, 855-867.
10. Raman, R., Raguram, S., Venkataraman, G., Paulson, J.C., Sasisekharan, R. Glycomics: an integrated systems approach to structure-function relationships of glycans. Nat. Methods 2005, 2, 817-824
11. Varki A. Glycan-based interactions involving vertebrate sialic-acid-recognizing proteins. Nature 2007, 446, 1023-1029.
12. Koeller, K.M., Wong, C.H. Complex carbohydrate synthesis tools for glycobiologists: enzyme-based approach and programmable one-pot strategies. Glycobiology 2000, 10, 1157-1169.
13. Szymanski, C.M., Wren, B.W. Protein glycosylation in bacterial pathogens. Nat. Rev. Microbiol. 2005, 3, 225-237.
14. Faridmoayer, A., Fentabil, M.A., Mills, D.C., Klassen, J.S., Feldman, M.F. Functional characterization of bacterial oligosaccharyltransferases involved in O-linked protein glycosylation. J Bacteriol. 2007, 189, 8088-8098.
15. Turnbull, W.B., Precious, B.L., Homans, S.W. Dissecting the cholera toxinganglioside GM1 interaction by isothermal titration calorimetry. J. Am. Chem. Soc. 2004, 126, 1047-1054.
16. Stussi, G., West, L., Cooper, D.K.C., Seebach, J.D. ABO-incompatible allotransplantation as a basis for clinical xenotransplantation. Xenotransplantation 2006, 13, 390-399.
17. Cooper, D.K.C., Gollackner, B., Sachs, D.H. Will the pig solve the transplantation blacklog? Annu. Rev. Med. 2002, 53, 133-147.
18. Gege, C., Kinzy, W., Schmidt, R.R. Total synthesis of the natural antigen involved in the hyperacute rejection response to xenotransplants. Carbohydr. Res. 2000, 328, 459-466.
19. Tai, H.C., Ezzelarab, M., Hara, H., Ayares, D., Cooper, D.K.C. Progress in xenotransplantation following the introduction of gene-knockout technology. Transplant Int. 2007, 20, 107-117.
20. Daubenspeck, J.M., Zeng, H., Chen, P., Dong, S., Steichen, C.T., Rama Krishna, N., et al. Novel oligosaccharide side chains of the collagen-like region of Bc1A, the major glycoprotein of the Bacillus anthracis exosporium. J. Biol. Chem. 2004, 279, 30945-3053.
21. Seeberger, P.H., Werz, D.B. Synthesis and medical applications of oligosaccharides. Nature 2007, 446, 1046-1051.
22. Werz, D.B., Seeberger, P.H. Total synthesis of antigen Bacillus anthracis tetrasaccharide-creation of an anthrax vaccine candidate. Angew. Chem. Int. Ed. 2005, 44, 6315-6318.
23. Paulson, J.C., Blixt, O., Collins, B. E. Sweet spots in functional glycomics. Nat. Chem. Biol. 2006, 2, 238-248.
24. Shriver, Z., Raguram, S., Sasisekha-ran, R. Glycomics: A pathway to a class of new and improved therapeutics. Nat. Rev. Drug Discov. 2004, 3, 863-873.
25. Zhu, X.M., Schmidt, R.R. New Principles for Glycoside-Bond Formation. Angew. Chem. Int. Ed. 2009, 48, 1900-1934.
26. Boltje, T.J., Buskas, T., Boons, G.J., Opportunities and challenges in synthetic oligosaccharide and glycoconjugate research. Nat. Chem. 2009, 1, 611-622.
27. Fraser-Reid, B.O., Tatsuta, K., Thiem, J. Glycoscience: Chemistry and Chemical Biology, 2nd ed., Springer, New York, 2008.
28. Kamerling, J.P., Comprehensive Glycoscience, Vol. 1-4, Elsevier, Dordrecht, 2007.
29. Wong, C.-H. Carbohydrate-Based Drug Discovery, Wiley-VCH, Weinheim, 2003.
30. Ernst, B., Hart, G.W., Sinay, P. Carbohydrates in Chemistry and Biology, Wiley-VCH, Weinheim, 2000.
31. Nicolaou, K.C., Mitchell, H.J. Adventures in carbohydrate chemistry: New synthetic technologies, chemical synthesis, molecular design, and chemical biology. Angew. Chem. Int. Ed. 2001, 40, 1576-1624.
32. Koeller, K.M., Wong, C.-H. Enzymes for chemical synthesis. Nature 2001, 409, 232-240.
33. Bertozzi, C.R., Kiessling, L.L., Chemical glycobiology. Science 2001, 291, 2357-2364.
34. Rudd, P.M., Dwek, R.A. Glycosylation: Heterogeneity and the 3D structure of proteins. Crit. Rev. Biochem. Mol. Biol. 1997, 32, 1-100.
35. Merrifield, R.B. Solid Phase Synthesis Angew. Chem., Int. Ed. Engl., 1985, 24, 799-810.
36. Caruthers, M.H. Gene synthesis machines: DNA chemistry and its uses. Science 1985, 230, 281-285.
37. Wong, C.-H. Protein glycosylation: New challenges and opportunities. J. Org. Chem. 2005, 70, 4219-4225.
38. Weishaupt, M., Eller, S., Seeberger, P.H. Solid phase synthesis of oligosaccharides. Method. Enzymol. 2010, 478, 463-484.
39. Mizuno, M., Kitazawa, S., Goto, K. p-Alkoxyphenyl-type heavy fluorous tag for the preparation of carbohydrate units. J. Fluorine Chem. 2008, 129, 955-960.
40. Hsu, C.-H., Hung, S.-C., Wu, C.-Y., Wong, C.-H. Toward Automated Oligosaccharide Synthesis Angew. Chem. Int. Ed. 2011, 50, 11872-11923.
41. Seeberger P.H., Automated oligosaccharide synthesis. Chem. Soc. Rev. 2008, 37, 19-28.
42. Filice, M., Guisan, J.M., Terreni, M., Palomo, J.M. Regioselective monodeprotection of peracetylated carbohydrates. Nat. Protoc. 2012, 7, 1783-1796.
43. Wang, C.-C., Kulkarni, S.S., Lee, J.-C., Luo S.-Y., Hung, S.-C. Regioselective one-pot protection of glucose. Nat. Protoc. 2008, 3, 97-113.
44. Crout, D.H., Vic, G. Glycosidases and glycosyl transferases in glycoside and oligosaccharide synthesis. Curr. Opin. Chem. Biol. 1998, 2, 98-111.
45. Kamerling, J.P., Comprehensive Glycoscience, Vol. 1-4, Elsevier, Dordrecht, 2007.
46. Weijers, C.A.G.M., Franssen, M.C.R., Visser, G.M. Glycosyltransferase-catalyzed synthesis of bioactive oligosaccharides. Biotechnol. Adv. 2008, 26, 436-456.
47. Trincone, A., Giordano, A. Glycosyl hydrolases and glycosyltransferases in the synthesis of oligosaccharides. Curr. Org. Chem. 2006, 10, 1163-1193.
48. Vasella, A., Davies, G.J, Böhm, M. Glycosidase mechanisms. Curr. Opin. Chem. Biol. 2002, 6, 619-629.
49. Withers, S.G. Mechanisms of glycosyl transferases and hydrolases. Carb. Polym. 2001, 44, 325-337.
50. Schmaltz, R.M., Hanson, S.R., Wong, C.-H. Enzymes in the Synthesis of Glycoconjugates. Chem. Rev. 2011, 111, 4259-4307.
51. Cobucci-Ponzano, B., Strazzulli, A., Rossi, M., Moracci, M., Glycosynthases in Biocatalysis. Adv. Synth. Catal. 2011, 353, 2284-2300.
52. Trincone, A., Giordano, A. Glycosyl hydrolases and glycosyltransferases in the synthesis of oligosaccharides. Curr Org Chem 2006, 10, 1163-1193.
53. Schuman, B., Alfaro, J.A., Evans, S.V. Glycosyltransferases structure and function. Top Curr Chem 2007, 272, 217-257.
54. Breton, C., Snajdrová, L., Jeanneau, C., Koca, J., Imberty, A. Structures and mechanisms of glycosyltransferases. Glycobiology 2006, 16, 29R-37R.
55. Lairson, L. L., Henrissat, B., Davies, G.J., Withers, S.G. Glycosyltransferases: structures, functions, and mechanisms. Annu. Rev. Biochem. 2008, 77, 521-555.
56. Schuman, B., Alfaro, J.A., Evans, S.V. Glycosyltransferase structure and function. Bioact. Conformation I 2007, 272, 217-257.
57. Breton, C., Snajdrová, L., Jeanneau, C., Koca, J., Imberty, A. Structures and mechanisms of glycosyltransferases. Glycobiology 2006, 16, 29R-37R.
58. Wagner, G. K., Pesnot, T. Glycosyltransferases and their assays. ChemBio-Chem 2010, 11, 1939-1949.
59. Coutinho, P.M., Deleury, E., Davies, G.J., Henrissat, B. An evolving hierarchical family classification for glycosyltransferases. J Mol Biol 2003, 328, 307-317.
60. Cantarel, B.L., Coutinho, P.M., Rancurel, C., Bernard, T., Lombard, V., Henrissat, B. The Carbohydrate-Active EnZymes database CAZy: an expert resource for glycogenomics. Nucleic Acids Res 2009, 37, D233-D238. http://www.cazy.org.
61. Leloir, L.F. Two Decades of Research on Biosynthesis of Saccharides. Science 1971, 172, 1299-1303.
62. Thibodeaux, C.J., Melançon, C.E., Liu, H.W. Unusual sugar biosynthesis and natural product glycodiversification. Nature 2007, 446, 1008-1016.
63. Breton, C., Mucha, J., Jeanneau, C. Structural and functional features of glycosyltransferases. Biochimie 2001, 83, 713-718.
64. Hu, Y., Walker, S. Remarkable structural similarities between diverse glycosyltransferases. Chem Biol 2002, 9, 1287-1296.
65. Maruta, K., Watanabe, H., Nishimoto, T., Kubota, M., Chaen, H., Fukuda, S., Kurimoto, M., Tsujisaka, Y. Acceptor specificity of trehalose phosphorylase from Thermoanaerobacter brockii: production of novel nonreducing trisaccharide, 6-O-D-galactopyranosyl trehalose. J Biosci Bioeng 2006, 101, 385-390.
66. Okada, H., Fukushi, E., Onodera, S., Nishimoto, T., Kawabata, J., Kikuchi, M., Shiomi, N. Synthesis and structural analysis of five novel oligosaccharides prepared by glucosyltransfer from D-glucose-1-phosphate to isokestose and nystose using Thermoanaerobacter brockii kojibiose phosphorylase. Carbohydr Res 2003, 338, 879-885.
67. Takahashi, N., Fukushi, E., Onodera, S., Benkeblia, N., Nishimoto, T., Kawabata, J., Shiomi, N. Three novel oligosaccharides synthesized using Thermoanaerobacter brockii kojibiose phosphorylase. Chem Centr J 2007, 1, 18-25.
68. Kitaoka, M., Phosphorylases in the production of oligosaccharides. ACS Symposium Series 2007, 972, 195-206.
69. Lairson, L.L., Withers, S.G. Mechanistic analogies amongst carbohydrate modifying enzymes. Chem. Commun. 2004, 20, 2243-2248.
70. Seibel, J., Jördening, H.J., Buchholz, K. Glycosylation with activated sugars using glycosyltransferases and transglycosidases. Biocatal. Biotransform. 2006, 24, 311-342.
71. Seibel, J., Moraru, R., Götze, S. Biocatalytic and chemical investigations in the synthesis of sucrose analogues. Tetrahedron 2005, 61, 7081-7086.
72. Seibel, J., Beine, R., Moraru, R., Behringer, C., Buchholz, K. A new pathway for the synthesis of oligosaccharides by the use of non-Leloir glycosyltransferases. Biocatal. Biotransform. 2006, 24, 157-165.
73. Qasba, P.K., Ramakrishnan, B., Boeggeman, E. Substrate-induced conformational changes in glycosyltransferases. Trends Biochem. Sci. 2005, 30, 54-62.
74. Ramakrishnan, B., Qasba, P.K. Crystal structure of lactose synthase reveals a large conformational change in its catalytic component, the 1,4-galactosyltransferase-I. J Mol Biol 2001, 310, 205-218.
75. Yamamoto, T., Takakura, Y., Hiroshi, T. Bacterial sialyltransferases. Trends Glycosci. Glyc. 2006, 18, 253-265.
76. Hennet, T. The galactosyltransferase family. Cell Mol Life Sci 2002, 59, 1081-1095.
77. Khaled, A., Piotrowska, O., Domniniak, K., Augé, C. Exploring specificity of glycosyltransferases: synthesis of new sugar nucleotide related molecules as putative donor substrates. Carbohydr Res 2008, 343, 167-178.
78. Seo, J.-H., Lee, W.-H., Chin, Y.-W., Han, N.S., Kim, M.-D. Enhanced production of GDP-l-fucose by overexpression of NADPH regenerator in recombinant Escherichia coli. Appl. Microbiol. Biot. 2011, 91, 967-976.
79. Drouillard, S., Mine, T., Kajiwara, H., Yamamoto, T., Samain, E. Efficient synthesis of 6'-sialylactose, 6,6'-disialyllactose, and 6'-KDOlactose by metabolically engineered E. coli expressing a multifunctional sialyltransferase from Photobacterium sp. JTISH-224. Carbohydr Res 2010, 345, 1394-1399.
80. Hanson, S., Best, M., Bryan, M.C., Wong, C.H. Chemoenzymatic synthesis of oligosaccharides and glycoproteins. Trends Biochem Sci 2004, 29, 656-663.
81. Koeller, K.M., Wong, C.H. Synthesis of complex carbohydrates and glycoconjugates: enzyme based and programmable one-pot strategies. Chem. Rev. 2000, 100, 4465-4493.
82. Koeller, K.M., Wong, C.-H. Enzymes for chemical synthesis. Nature 2001, 409, 232-240.
83. Elling, L. Glycobiotechnology: enzymes for the synthesis of nucleotide sugars. Adv. Biochem. Eng. Biotechnol. 1997, 58, 89-144.
84. Zervosen, A., Elling, L. A Novel Three-Enzyme Reaction Cycle for the Synthesis of N-Acetyllactosamine with in Situ Regeneration of Uridine 5'-Diphosphate Glucose and Uridine 5'-Diphosphate Galactose. J. Am. Chem. Soc. 1996, 118, 1836-1840.
85. Rupprath, C., Kopp, M., Hirtz, D., Mueller, R., Elling, L. An Enzyme Module System for in situ Regeneration of Deoxythymidine 5-Diphosphate (dTDP)-Activated Deoxy Sugars. Adv. Synth. Catal. 2007, 349, 1489-1496.
86. Masada, S., Kawase, Y., Nagatoshi, M., Oguchi, Y., Terasaka, K., Mizukami, H. An efficient chemoenzymatic production of small molecule glucosides with in situ UDP-glucose recycling. FEBS Lett. 2007, 581, 2562-2566.
87. Muthana, S., Cao, H., Chen, X. Recent progress in chemical and chemoenzymatic synthesis of carbohydrates. Curr. Opin. Chem. Biol. 2009, 13, 573-581.
88. Harvey, D.J. Analysis of carbohydrates and glycoconjugates by matrixassisted laser desorption/ionization mass spectrometry: an update covering the period 2001-2002. Mass Spectrom. Rev. 2008, 27, 125-201.
89. Duffels, A., Green, L.G., Lenz, R., Ley, S.V., Vincent, S.P., Wong, C.-H. Chemoenzymatic synthesis of L-galactosylated dimeric sialyl LewisX structures employing alpha-1,3-fucosyltransferase V. Bioorg. Med. Chem. 2000, 8, 2519-2525.
90. Pudelko, M., Bull, J., Kunz, H. Chemical and Chemoenzymatic Synthesis of Glycopeptide Selectin Ligands Containing Sialyl LewisX Structures. ChemBioChem 2010, 11, 904-930.
91. Angata, T., Varki, A. Chemical diversity in the sialic acids and related alpha-keto acids: an evolutionary perspective. Chem. Rev. 2002, 102, 439-469.
92. Schwardt, O., Visekruna, T., Rabbani, S., Ernst, B. Bacterial Sialyltransferases for Carbohydrate Synthesis. Chimia 2006, 60, 234-260.
93. Li, Y., Chen, X. Sialic acid metabolism and sialyltransferases: natural functions and applications. Appl Microbiol Biotechnol 2012, 94, 887-905.
94. Ichikawa, Y., Lin, Y.C., Dumas, D.P., Shen, G.J., Garcia-Junceda, E., Williams, M.A., Bayer, R., Ketcham, C., Walker, L.E., Paulson, J.C., Wong, C.-H. Chemical-enzymatic synthesis and conformational analysis of sialyl Lewisx and derivatives. J. Am. Chem. Soc. 1992, 114, 9283-9298.
95. Cao, H., Huang, S., Cheng, J., Li, Y., Muthana, S., Son, B., Chen, X. Chemical preparation of sialyl Lewisx using an enzymatically synthesized sialoside building block. Carbohydr. Res. 2008, 343, 2863-2869.
96. Pukin, A.V., Weijers, C.A.G.M., van Lagen, B., Wechselberger, R., Sun, B., Gilbert, M., Karwaski, M.F., Florack, D.E., Jacobs, B.C., Tio-Gillen, A.P., van Belkum, A., Endtz, H.P., Visser, G.M., Zuilhof, H. GM3, GM2 and GM1 mimics designed for biosensing: chemoenzymatic synthesis, target affinities and 900 MHz NMR analysis. Carbohydr Res 2008, 343, 636-50.
97. Palcic, M.M. Glycosyltransferases as biocatalysts. Curr. Opin. Chem. Biol. 2011, 15, 226-233.
98. Trincone A, Giordano A. Glycosyl hydrolases and glycosyltransferases in the synthesis of oligosaccharides. Curr Org Chem 2006, 10, 1163-1193.
99. Helenius, A., Aebi, M. Roles of N-linked glycans in the endoplasmic reticulum. Annu. Rev. Biochem. 2004, 73, 1019-1049.
100. Hancock, S. M., Vaughan, M. D., Withers, S.G. Engineering of glycosidases and glycosyltransferases. Curr. Opin. Chem. Biol. 2006, 10, 509-519.
101. Palcic, M.M. Biocatalytic synthesis of oligosaccharides. Curr Opin Biotechnol 1999, 10, 616-624.
102. Bojarov-Fialov, P., Ken, V. Comprehensive Glycoscience, (Ed.: P. K. Johannis), Elsevier, Oxford, 2007.
103. Wang, L.X., Huang, W. Enzymatic transglycosylation for glycoconjugate synthesis. Curr. Opin. Chem. Biol. 2009, 13, 592-600.
104. Luley-Goedl, C., Nidetzky, B. Carbohydrate synthesis by disaccharide phosphorylases: reactions, catalytic mechanisms and application in the glycosciences. Biotechnol. J. 2010, 5, 1324.
105. Wong, C.-H., Halcomb, R.L., Ichikawa, Y., Kajimoto, T. Enzymes in organic synthesis: Application to the problems of carbohydrate recognition (part 2). Angew. Chem., Int. Ed. 1995, 34, 521-546.
106. Watt, G.M., Lowden, P.A., Flitsch, S.L. Enzyme-catalyzed formation of glycosidic linkages. Curr. Opin. Struct. Biol. 1997, 7, 652-660.
107. Sinnott, M.L. Catalytic mechanisms of enzymic glycosyl transfer. Chem. Rev. 1990, 90, 1171-1202.
108. Song, J., Zhang, H., Li, L., Bi, Z., Chen, M., Wang, W., Yao, Q., Guo, H., Tian, M., Li, H., Yi, W., Wang, P.G. Enzymatic biosynthesis of oligosaccharides and glycoconjugates. Curr. Org. Synth. 2006, 3, 159-168.
109. Gallego, R.G., Dudziak, G., Kragl, U., Wandrey, C., Kamerling, J.P., Vliegenthart, J.F.G. Enzymatic synthesis of the core-2 sialyl LewisX Oglycan on the tumor-associated MUC1a' peptide. Biochimie 2003, 85, 275-286.
110. Ajisaka, K., Miyasato, M. Efficient synthesis of a sialyl T-antigenlinked glycopeptide by the chemoenzymatic method. Biosci. Biotechnol. Biochem. 2000, 64, 1743-1746.
111. Nishio, T., Hoshino, S., Kondo, A., Ogawa, M., Matsuishi, Y., Kitagawa, M., Kawachi, R., Oku, T. alpha-Mannosidase-catalyzed synthesis of a (1-->2)-alpha-D-rhamnodisaccharide derivative. Carbohydr. Res. 2004, 339, 1389-1393.
112. Faijes, M., Planas, A. In vitro synthesis of artificial polysaccharides by glycosidases and glycosynthases. Carbohydr. Res. 2007, 342, 1581-1594.
113. Hamilton, C.J. Enzymes in preparative mono-and oligo-saccharide synthesis. Nat. Prod. Rep. 2004, 21, 365-385.
114. Wang, L.-X. Chemoenzymatic synthesis of glycopeptides and glycoproteins through endoglycosidase-catalyzed transglycosylation. Carbohydr. Res. 2008, 343, 1509-1522.
115. Akaike, E., Tsutsumida, M., Osumi, K., Fujita, M., Yamanoi, T., Yamamoto, K., Fujita, K. High efficiency of transferring a native sugar chain from a glycopeptide by a microbial endoglycosidase in organic solvents. Carbohydr. Res. 2004, 339, 719-722.
116. Kittl, R., Withers, S.G. New approaches to enzymatic glycoside synthesis through directed evolution. Carbohydr. Res. 2010, 345, 1272-1279.
117. Kobayashi, S. New Developments of Polysaccharide Synthesis via Enzymatic Polymerization Proc. Jpn. Acad., Ser. B 2007, 83, 215-247.
118. Williams, S.J., Withers, S.G. Glycosyl fluorides in enzymatic reactions Carbohydr. Res. 2000, 327, 27-46.
119. Shoda, S., Kiyosada, T., Mori, H., Kobayashi, S. Chitinase-catalyzed synthesis of oligosaccharides by using a sugar oxazoline as glycosyl donor. Heterocycles 2000, 52, 599-602.
120. Kobayashi, A.; Kuwata, H.; Kohri, M.; Izumi, R.; Watanabe, T.; Shoda, S. A Bacterial Chitinase Acts as Catalyst for Synthesis of the N-Linked Oligosaccharide Core Trisaccharide by Employing a Sugar Oxazoline Substrate. J. Carbohydr. Chem. 2006, 25, 533-541.
121. Li, B., Song, H., Hauser, S., Wang, L.-X. A highly efficient chemoenzymatic approach toward glycoprotein synthesis. Org. Lett. 2006, 8, 3081-3084.
122. Zeng, Y., Wang, J., Li, B., Hauser, S., Li, H., Wang, L.-X. Glycopeptide synthesis through endo-glycosidase-catalyzed oligosaccharide transfer of sugar oxazolines: probing substrate structural requirement. Chem. Eur. J. 2006, 12, 3355-3364.
123. Wei, Y., Li, C., Huang, W., Li, B., Strome, S., Wang, L.-X. Glycoengineering of human IgG1-Fc through combined yeast expression and in vitro chemoenzymatic glycosylation. Biochemistry 2008, 47, 10294-10304.
124. Li, B., Zeng, Y., Hauser, S., Song, H., Wang, L.-X. Highly efficient endoglycosidase-catalyzed synthesis of glycopeptides using oligosaccharide oxazolines as donor substrates. J. Am. Chem. Soc. 2005, 127, 9692-9693.
125. Li, H., Li, B., Song, H., Breydo, L., Baskakov, I. V., Wang, L.-X. Chemoenzymatic synthesis of HIV-1 V3 glycopeptides carrying two N-glycans and effects of glycosylation on the peptide domain. J. Org. Chem. 2005, 70, 9990-9996.
126. Rising, T.W., Heidecke, C.D., Moir, J.W., Ling, Z., Fairbanks, A.J. Endohexosaminidase-catalysed glycosylation with oxazoline donors: fine tuning of catalytic efficiency and reversibility. Chem. Eur. J. 2008, 14, 6444-6464.
127. Cobucci-Ponzano, B., Zorzetti, C., Strazzulli, A., Bedini, E., Corsaro, M.M., Sulzenbacher, G., Rossi, M., Moracci, M. Exploitation of glycosyl azides for the preparation of glycosynthases Biocatal. Biotransform. 2012, 30, 288-295.
128. Bojarová, P., Petrásková, L., Ferrandi, E. E., Monti, D., Pelantová, H., Kuzma, M., Simerská, P., Kcen, V. Glycosyl azides-an alternative way to disaccharides. Adv. Synth. Catal. 2007, 349, 1514-1520.
129. Garner, B., Merry, A.H., Royle, L., Harvey, D.J., Rudd, P.M., Thillet, J. Structural elucidation of the N-and O-glycans of human apolipoprotein(a): role of o-glycans in conferring protease resistance. J. Biol. Chem. 2001, 276, 22200-22208.
130. Lee, J.E., Fusco, M.L., Abelson, D.M., Hessell, A.J., Burton, D.R., Saphire, E.O. Techniques and tactics used in determining the structure of the trimeric ebolavirus glycoprotein. Acta Crystallogr., Sect. D: Biol. Crystallogr. 2009, 65, 1162-1180.
131. Lee, J.E., Fusco, M.L., Saphire, E.O. An efficient platform for screening expression and crystallization of glycoproteins produced in human cells. Nat. Protoc. 2009, 4, 592-604.
132. Wang, C.C., Chen, J.R., Tseng, Y.C., Hsu, C.H., Hung, Y.F., Chen, S.W., Chen, C.M., Khoo, K.H., Cheng, T.J., Cheng, Y.S., Jan, J.T., Wu, C.Y., Ma, C., Wong, C.-H. Glycans on influenza hemagglutinin affect receptor binding and immune response. Proc. Natl. Acad. Sci. U. S. A. 2009, 106, 18137-18142.
133. Wang, L.X. The amazing transglycosylation activity of endo-beta-Nacetylglucosaminidases. Trends Glycosci. Glycotechnol. 2011, 23, 33-52.
134. Fujita, K., Yamamoto, K. A remodeling system for the oligosaccharide chains on glycoproteins with microbial endo-beta-N-acetylglucosaminidases. Biochim. Biophys. Acta 2006, 1760, 1631-1635.
135. Li, H., Singh, S., Zeng, Y., Song, H., Wang, L.-X. Chemoenzymatic synthesis of CD52 glycoproteins carrying native N-glycans. Bioorg. Med. Chem. Lett. 2005, 15, 895-898.
136. Tomabechi, Y., Suzuki, R., Haneda, K., Inazu, T. Chemo-enzymatic synthesis of glycosylated insulin using a GlcNAc tag. Bioorg. Med. Chem. 2010, 18, 1259-1264.
137. Haneda, K., Tagashira, M., Yoshino, E., Takeuchi, M., Inazu, T., Toma, K., Iijima, H., Isogai, Y., Hori, M., Takamatsu, S., Fujibayashi, Y., Kobayashi, K., Takeuchi, M., Yamamoto, K. Chemo-enzymatic synthesis and structure-activity study of artificially N-glycosylated eel calcitonin derivatives with a complex type oligosaccharide. Glycoconj. J. 2004, 21, 377-386.
138. Umekawa, M., Huang, W., Li, B., Fujita, K., Ashida, H., Wang, L.-X.; Yamamoto, K. Mutants of Mucor hiemalis endo-beta-Nacetylglucosaminidase show enhanced transglycosylation and glycosynthaselike activities. J. Biol. Chem. 2008, 283, 4469-4479.
139. Heidecke, C.D., Ling, Z., Bruce, N. C., Moir, J.W., Parsons, T.B., Fairbanks, A.J. Enhanced glycosylation with mutants of endohexosaminidase A (endo A). ChemBioChem 2008, 9, 2045-2051.
140. Ochiai, H., Huang, W., Wang, L.-X. Expeditious chemoenzymatic synthesis of homogeneous N-glycoproteins carrying defined oligosaccharide ligands. J. Am. Chem. Soc. 2008, 130, 13790-13803.
141. Parsons, T.B., Moir, J.W.B., Fairbanks, A.J. Synthesis of a truncated biantennary complex type N-glycan oxazoline; glycosylation catalysed by the endohexosaminidases Endo A and Endo M. Org. Biomol. Chem. 2009, 7, 3128-3140.
142. Adam, A.C., Rubio-Texeira, M., Polaina, J. Lactose: the milk sugar from a biotechnological perspective. Crit. Rev. Food Sci. 2004, 44, 553-557.
143. Park, A.R., Oh, D.K. Galacto-oligosaccharide production using microbial galactosidase: current state and perspectives. Appl. Microbiol. Biotechnol. 2010, 85, 1279-1286.
144. Rodriguez-Colinas, B., Poveda, A., Jimenez-Barbero, J., Ballesteros, A.O., Plou, F.J. Galacto-oligosaccharide Synthesis from Lactose Solution or Skim Milk Using the Galactosidase from Bacillus circulans. J. Agric. Food Chem. 2012, 60, 6391-6398.
145. Royle, L., Radcliffe, C.M., Dwek, R.A., Rudd, P.M. Detailed structural analysis of N-glycans released from glycoproteins in SDS-PAGE gel bands using HPLC combined with exoglycosidase array digestions. Methods Mol. Biol. 2006, 347, 125-143.
146. Liu, Q.P., Yuan, H., Bennett, E.P., Levery, S.B., Nudelman E, Spence, J., Pietz, G., Saunders, K., White, T., Olsson, M.L., Henrissat, B., Sulzenbacher, G., Clausen, H. Identification of a GH110 subfamily of α1,3-galactosidases: novel enzymes for removal of the α3Gal xenotransplantation antigen. J. Biol. Chem. 2008, 283, 8545-8554.
147. Liu, Q.P., Sulzenbacher, G, Yuan H, Bennett, E.P., Pietz, G., Saunders, K., Spence, J., Nudelman, E., Levery, S.B., White, T., Neveu, J.M., Lane, W.S., Bourne, Y., Olsson, M.L., Henrissat, B., Clausen, H. Bacterial glycosidases for the production of universal red blood cells. Nat. Biotechnol. 2007, 25, 454-464.
148. Kobayashi, S., Kashiwa, K., Kawasaki, T., Shoda, S. Novel Method for Polysaccharide Synthesis Using an Enzyme: The First in Vitro Synthesis of Cellulose via Non biosynthetic Path Utilizing Cellulase as Catalyst. J. Am. Chem. Soc. 1991, 113, 3079-3084.
149. Shoda, S., Kobayashi, S. Enzymatic polymerization to polysaccharides of well-defined structure. Macromol. Symp. 1995, 99, 179-184.
150. Shoda, S., Izumi, R., Fujita, M. Green process in glycotechnology. Bull. Chem. Soc. Jpn. 2003, 76, 1-13.
151. Roy, D., Semsarilar, M., Guthrie, J.T., Perrier, S. Cellulose modification by polymer grafting: a review. Chem. Soc. Rev. 2009, 38, 2046-2064.
152. Okamoto, E., Kiyosada, T., Shoda, S.I., Kobayashi, S. Synthesis of Alternatingly 6-O-Methylated Cellulose via Enzymatic Polymerization of a Substituted Cellobiosyl Fluoride Monomer Catalyzed by Cellulase. Cellulose 1997, 4, 161-172.
153. Kobayashi, S., Ohmae, M. Enzymatic polymerization to polysaccharides. Adv. Polym. Sci. 2006, 194, 159-210.
154. Bojarová, P., Kcenek, K., Kuzma, M., Petrásková, L., Bezouka, K., Namdjou, D.-J., Elling, L., Kcen, V. N-Acetylhexosamine triad in one molecule: Chemoenzymatic introduction of 2-acetamido-2-deoxy-Dgalactopyranosyluronic acid residue into a complex oligosaccharide. J. Mol. Catal. B Enzym. 2008, 50, 69-73.
155. Fialová, P., Namdjou, D.-J., Ettrich, R., Psikrylová, V., Rauvolfová, J., Ksenek, K., Kuzma, M., Elling, L., Bezoucka, K., Kcen, V. Combined application of galactose oxidase and -N acetylhexosaminidase in the synthesis of complex immunoactive N-acetyl-Dgalactosaminides. Adv. Synth. Catal. 2005, 347, 997-1006.
156. Hamilton, C.J. Enzymes in preparative mono-and oligo-saccharide synthesis. Nat. Prod. Rep. 2004, 21, 365-385.
157. Faijes, M., Planas, A. In vitro synthesis of artificial polysaccharides by glycosidases and glycosynthases. Carbohydr. Res. 2007, 342, 1581-1594.
158. Mackenzie, L.F., Wang, Q., Warren, R.A.J., Withers, S.G. Glycosynthases: Mutant Glycosidases for Oligosaccharide Synthesis. J. Am. Chem. Soc. 1998, 120, 5583-5584.
159. Malet, C., Planas, A. From glucanase to glucansynthase: Glycosyl transfer to glycosyl fluorides catalyzed by a mutant endoglucanase lacking its catalytic nucleophile. FEBS Lett. 1998, 440, 208-212.
160. Moracci, M., Trincone, A., Perugino, G., Ciaramella, M., Rossi, M. Restoration of the activity of active-site mutants of the hyperthermophilic glycosidase from Sulfolobus solfataricus: Dependence of the mechanism on the action of external nucleophiles. Biochemistry 1998, 37, 17262-17270.
161. Wang, L.-X. Expanding the repertoire of glycosynthases. Chem. Biol. 2009, 16, 1026-1027.
162. Kittl, R., Withers, S.G. New approaches to enzymatic glycoside synthesis through directed evolution. Carbohydr. Res. 2010, 345, 1272-1279.
163. Viladot, J.L. de Ramon, E., Durany, O. Planas, A. Probing the mechanism of Bacillus 1,3-1,4-D-glucan 4-glucanohydrolases by chemical rescue of inactive mutants at catalytically essential residues. Biochemistry 1998, 37, 11332-11342.
164. Perugino G, Cobucci-Ponzano B, Rossi M, Moracci M. Recent advances in the oligosaccharide synthesis promoted by catalytically engineered glycosidases. Adv Synth Catal 2005, 347, 941-950.
165. Yang, M, Davies, G.J., Davis, B.G. A glycosynthase catalyst for the synthesis of flavonoid glycosides. Angew. Chem. Int. Ed. 2007, 46, 3885-3888.
166. Cobucci-Ponzano, B., Perugino, G., Strazzulli, A., Rossi, M., Moracci, M. Thermophilic glycosynthases for oligosaccharides synthesis. Method. Enzymol. 2012, 510, 273-300.
167. Rich, J.R., Cunningham, A.-M., Gilbert, M., Withers, S.G. Glycosphingolipid synthesis employing a combination of recombinant glycosyltransferases and an endoglycoceramidase glycosynthase. Chem. Commun. 2011, 47, 10806-10808.
168. Spadiut, O., Ibatullin, F.M., Peart, J., Gullfot, F., Martinez-Fleites, C., Ruda, M., Xu, C., Sundqvist, G., Davies, G.J., Brumer, H. Building custom polysaccharides in vitro with an efficient, broadspecificity xyloglucan glycosynthase and a fucosyltransferase. J. Am. Chem. Soc., 2011, 133, 10892-10900.
169. Cobucci-Ponzano, B., Moracci, M. Glycosynthases as tools for the production of glycan analogs of natural products. Nat. Prod. Rep., 2012, 29, 697-709.
170. Pérez, X., Faijes, M., Planas, A. Artificial mixed-linked glucans produced by glycosynthase-catalyzed polymerization: Tuning morphology and degree of polymerization. Biomacromolecules 2011, 12, 494-501.
171. Perugino, G., Trincone, A., Rossi, M., Moracci, M. Oligosaccharide synthesis by glycosynthases. Trends Biotechnol 2004, 22, 31-37;
172. Viladot, J.L., Canals, F., Barllori, X., Planas, A. Long-lived glycosyl-enzyme intermediate mimic produced by formate re-activation of a mutant endoglucanase lacking its catalytic nucleophile. Biochem. J. 2001, 355, 79-86.
173. Mayer, C., Zechel D.L., Reid, S.P., Warren, R.A.J., Withers, S.G. The E358S mutant of Agrobacterium sp. glucosidase is a greatly improved glycosynthase. FEBS Lett. 2000, 466, 40-44.
174. Gunther, W., Kunz, H., Synthesis of D-mannosides from D-glucosides via an intramolecular SN2 reaction at C-2. Carbohydr. Res. 1992, 228, 217-241.
175. Nashiru, O., Zechel D.L., Stoll, D., Mohammadzadeh, T., Warren, R.A., Withers, S.G., Mannosynthase: synthesis of mannosides with a mutant mannosidase. Angew. Chem. Int. Ed. Engl 2001, 40, 417-420.
176. Jahn, M., Stoll, D., Warren, R.A., Szabo, L., Singh, P., Gilbert, H.J., Ducros, V.M., Davies, G.J., Withers, S.G. Expansion of the glycosynthase repertoire to produce defined manno-oligosaccharides. Chem. Commun. (Camb.) 2003, 12, 1327-1329.
177. Drone, J., Feng, H.Y., Tellier, C., Hoffmann, L., Tran, V., Rabiller, C., Dion, M. Thermus thermophilus glycosynthases for the efficient synthesis of galactosyl and glucosyl (1-3)-glycosides. Eur. J. Org. Chem. 2005, 10, 1977-1983.
178. Trincone, A. Giordano, A., Perugino, G., Rossi, M., Moracci, M. Highly productive autocondensation and transglycosylation reactions with Sulfolobus solfataricus glycosynthase. ChemBioChem 2005, 6, 1431-1437.
179. Mullegger, J. Chen, H.M., Chan, W.Y., Reid, S.P., Jahn, M., Warren, R.A., Salleh, H.M., Withers, S.G. Thermostable glycosynthases and thioglycoligases derived from Thermotoga maritima glucuronidase. ChemBioChem 2006, 7, 1028-1030.
180. Wilkinson, S.M., Liew, C.W., Mackay, J.P., Salleh, H.M., Withers, S.G., McLeod M.D. Escherichia coli glucuronylsynthase: an engineered enzyme for the synthesis of glucuronides. Org. Lett. 2008, 10, 1585-1588.
181. Honda, Y., Kitaoka, M. The first glycosynthase derived from an inverting glycoside hydrolase. J. Biol. Chem. 2006, 281, 1426-1431.
182. Wada, J., Honda, Y., Nagae, M., Kato, R., Wakatsuki, S., Katayama, T., Taniguchi, H., Kumagai, H., Kitaoka, M., Yamamoto, K. 1,2-alpha-l-Fucosynthase: a glycosynthase derived from an inverting alpha-glycosidase with an unusual reaction mechanism. FEBS Lett. 2008, 582, 3739-3743.
183. Vaughan, M.D., Johnson, K., DeFrees, S., Tang, X., Warren, R.A., Withers, S.G. Glycosynthase-mediated synthesis of glycosphingolipids. J. Am. Chem. Soc. 2006, 128, 6300-6301.
184. Perugino, G., Cobucci-Ponzano, B., Rossi, M., Moracci, M. Recent advances in the oligosaccharide synthesis promoted by catalytically engineered glycosidases. Adv. Synth. Catal. 2005, 347, 941-950.
185. Umekawa, M., Li, C., Higashiyama, T., Huang, W., Ashida, H., Yamamoto, K., Wang, L.-X. Efficient glycosynthase mutant derived from Mucor hiemalis endo-beta-N-acetylglucosaminidase capable of transferring oligosaccharide from both sugar oxazoline and natural N-glycan. J. Biol. Chem. 2010, 285, 511-521.
186. van Lieshout, J., Faijes, M., Nieto, J., van der Oost, J., Planas, A. Hydrolase and glycosynthase activity of endo-1,3-beta-glucanase from the thermophile Pyrococcus furiosus. Archaea 2004, 1, 285-292.
187. Yin, J., Li, L.; Shaw, N., Li, Y., Song, J. K., Zhang, W., Xia, C., Zhang, R., Joachimiak, A., Zhang, H.-C., Wang, L.-X., Liu, Z.-J., Wang, P. Structural basis and catalytic mechanism for the dual functional endobeta-N-acetylglucosaminidase A. PLoS One 2009, 4, e4658;
188. Hancock, S.M., Rich, J.R., Caines, M.E., Strynadka, N.C., Withers, S.G. Designer enzymes for glycosphingolipid synthesis by directed evolution. Nat. Chem. Biol. 2009, 5, 508-514.
189. Cobucci-Ponzano, B., Conte, F., Bedini, E., Corsaro, M.M., Parrilli, M., Sulzenbacher, G., Lipski, A., Dal Piaz, F., Lepore, L., Rossi, M., Moracci, M. Glycosyl Azides as Substrates for Glycosynthases: Preparation of Efficient L-Fucosynthases. Chem. Biol. 2009, 16, 1097-1108.
190. Cobucci-Ponzano, B., Zorzetti, C., Strazzulli, A., Carillo, S., Bedini, E., Corsaro, M.M., Comfort, D.A., Kelly, R.M., Rossi, M., Moracci, M. A novel-dgalactosynthase from Thermotoga maritima converts-D-galactopyranosyl azide to-galacto-oligosaccharides. Glycobiology 2011, 21, 448-456.
191. M. Okuyama, H. Mori, K. Watanabe, A. Kimura, S. Chiba, Alpha-glucosidase mutant catalyzes alpha-glycosynthase-type reaction. Biosci. Biotechnol. Biochem. 2002, 66, 928-933.
192. Vanhooren, P.T., Vandamme, E.J. L-Fucose: occurrence, physiological role, chemical, enzymatic and microbial synthesis. J. Chem. Technol. Biotechnol. 1999, 74, 479-497.
193. Macher, B.A., Galili, U. The Gal 1,3Gal 1,4GlcNAc-R Gal epitope: a carbohydrate of unique evolution and clinical relevance. BBA Gen Subjects 2008, 1780, 75-88.
194. Yamamoto, K., Davis, B.G. Creation of an Mannosynthase from a Broad Glycosidase Scaffold. Angew Chem Int Ed Engl. 2012, 51, 7449-7453.
195. Yip, V.L., Varrot, A., Davies, G.J., Rajan, S.S., Yang, X., Thompson, J., Anderson, W.F., Withers, S.G. An unusual mechanism of glycoside hydrolysis involving redox and elimination steps by a family 4 beta-glycosidase from Thermotoga maritima. J. Am. Chem. Soc. 2004, 126, 8354-8355.
196. Rajan, S.S., Yang, X., Collart, F., Yip, V.L., Withers, S.G., Varrot, A., Thompson, J., Davies, G.J., Anderson, W.F. Novel catalytic mechanism of glycoside hydrolysis based on the structure of an NAD+/Mn2+-dependent phosphoalpha-glucosidase from Bacillus subtilis. Structure 2004, 12, 1619-1629.
197. Wang, L.-X, Lomino, J., Emerging Technologies for Making Glycan-Defined Glycoproteins. ACS Chem. Biol. 2012, 7, 110-122.