Page 180 - Cascade_Biocatalysis_Integrating_Stereoselective_and_Environmentally_Friendly_Reactions

156 6 Chemo-Enzymatic Cascade Reactions for the Synthesis of Glycoconjugates

of nucleotide-activated disaccharides. disaccharide mimetics using β-N-
Enzyme Microb. Technol., 34, 407–414. acetylhexosaminidases from Aspergillus
48. Sandoval, M., Ferreras, E., oryzae and Vigna radiata. Tetrahedron:
P´ erez-S´ anchez, M., Berenguer, J., Asymmetry, 16, 255–260.
Sinisterra, J.V., and Hernaiz, M.J. 55. McCarter, J.D. and Withers, S.G. (1994)
(2012) Screening of strains and Mechanisms of enzymatic glycoside
recombinant enzymes from Ther- hydrolysis. Curr. Opin. Struct. Biol., 4,
musthermophilusfor theiruse in 885–892.
disaccharide synthesis. J. Mol. Catal. B: 56. Fairbanks, A.J. (2011) Endohex-
Enzym., 74, 162–169. osaminidase catalysed glycosylation
49. Ashida, H., Ozawa, H., Fujita, K., with oxazoline donors: the develop-
Suzuki, S., and Yamamoto, K. ment of robust biocatalytic methods
(2010) Syntheses of mucin-type O- for synthesis of defined homogeneous
glycopeptides and oligosaccharides glycoconjugates. C.R. Chim., 14, 44–58.
using transglycosylation and reverse- 57. Huang, W., Li, J., and Wang, L.-X.
hydrolysis activities of Bifidobacterium (2011) Unusual transglycosylation activ-
endo-alpha-N-acetylgalactosaminidase. ity of flavobacterium meningosepticum
Glycoconjugate J., 27, 125–132. endoglycosidases enables convergent
50. Ashida, H., Yamamoto, K., Murata, chemoenzymatic synthesis of core
T., Usui, T., and Kumagai, H. fucosylated complex N-glycopeptides.
(2000) Characterization of endo- ChemBioChem, 12, 932–941.
α-N-acetylgalactosaminidase from 58. Kobayashi, S., Kiyosada, T., and Shoda,
Bacillus sp. and syntheses of neo- S. (1997) A novel method for synthesis
oligosaccharides using its transglycosy- of chitobiose via enzymatic glycosyla-
lation activity. Arch. Biochem. Biophys., tion using a sugar oxazoline as glycosyl
373, 394–400. donor. Tetrahedron Lett., 38, 2111–2112.
51. Park, A.R., Kim, H.J., Lee, J.K., and 59. Mackenzie, L.F., Wang, Q., Warren,
Oh, D.K. (2010) Hydrolysis and trans- R.A.J., and Withers, S.G. (1998) Gly-
glycosylation activity of a thermostable cosynthases: mutant glycosidases for
recombinant beta-glycosidase from sul- oligosaccharide synthesis. J. Am. Chem.
folobus acidocaldarius. Appl. Biochem. Soc., 120, 5583–5584.
Biotechnol., 160, 2236–2247. 60. Okuyama, M., Mori, H., Watanabe,
52. Bojarova, P., Krenek, K., Kuzma, K., Kimura, A., and Chiba, S. (2002)
M., Petraskova, L., Bezouska, K., Alpha-glucosidase mutant catalyzes
Namdjou, D.-J., Elling, L., and Kren, ‘‘alpha-glycosynthase’’-type reac-
V. (2008) N-acetylhexosamine triad tion. Biosci. Biotechnol. Biochem., 66,
in one molecule: chemoenzymatic 928–933.
introduction of 2-acetamido-2-deoxy-β- 61. Cobucci-Ponzano, B., Conte, F.,
D-galactopyranosyluronic acid residue Bedini, E., Corsaro, M.M., Parrilli, M.,
into a complex oligosaccharide. J. Mol. Sulzenbacher, G., Lipski, A., Dal Piaz,
Catal. B: Enzym., 50, 69–73. F., Lepore, L., Rossi, M. et al. (2009)
53. Fialov´ a, P., Namdjou, D.-J., Ettrich, Beta-glycosyl azides as substrates for
R., Pˇ rikrylov´ a, V., Rauvolfov´ a, J., alpha-glycosynthases: preparation of
Kˇ renek, K.,Kuzma,M., Elling,L., efficient alpha-L-fucosynthases. Chem.
Bezouˇ ska, K., and Kˇ ren, V. (2005) Biol., 16, 1097–1108.
Combined application of galactose oxi- 62. Cobucci-Ponzano, B. and Moracci, M.
dase and β-N-acetylhexosaminidase in (2012) Glycosynthases as tools for the
the synthesis of complex immunoac- production of glycan analogs of natural
tive N-acetyl-D-galactosaminides. Adv. products. Nat. Prod. Rep., 29, 697–709.
Synth. Catal., 347, 997–1006. 63. Hancock, S.M., Vaughan, M.D., and
54. Lakshmanan, T. and Loganathan, Withers, S.G. (2006) Engineering of
D. (2005) Enzymatic synthesis glycosidases and glycosyltransferases.
of N-glycoprotein linkage region Curr. Opin. Chem. Biol., 10, 509–519.