References
- Albert M, Repetschnigg W, Ortner J, Gomes J, Paul BJ, Illaszewicz C, . 2000. Simultaneous detection of different glycosidase activities by 19F NMR spectroscopy. Carbohydr Res 327: 395–400.
- Ausili A, Di Lauro B, Cobucci-Ponzano B, Bertoli E, Scirè A, Rossi M, Tanfani F, Moracci M. 2004. Two-dimensional IR correlation spectroscopy of mutants of the beta-glycosidase from the hyperthermophilic archaeon Sulfolobus solfataricus identifies the mechanism of quaternary structure stabilization and unravels the sequence of thermal unfolding events. Biochem J 384:69–78.
- Ben-David A, Shoham G, Shoham, Y. 2008. A universal screening assay for glycosynthases: directed evolution of glycosynthase XynB2 E335G suggests a general path to enhance activity. Chem Biol 15:546–551.
- Bojarová P, Kren V. 2009 Glycosidases: a key to tailored carbohydrates. Trends Biotechnol. 27:199–209.
- Cantarel BL, Coutinho PM, Rancurel C, Bernard T, Lombard V, Henrissat B. 2009. The Carbohydrate-Active EnZymes dat-abase CAZy: an expert resource for glycogenomics. Nucleic Acids Res 37:D233–D238.
- Cobucci-Ponzano B, Trincone A, Giordano A, Rossi M, Moracci M. 2003a. Identification of the catalytic nucleophile of the family 29 alpha-L-fucosidase from Sulfolobus solfataricus via chemical rescue of an inactive mutant. Biochemistry 42: 9525–9531.
- Cobucci-Ponzano B, Trincone A, Giordano A, Rossi M, Moracci M. 2003b. Identification of an archaeal alpha-L-fucosidase encoded by an interrupted gene. Production of a functional enzyme by mutations mimicking programmed –1 frameshifting. J Biol Chem 278:14622–14631.
- Cobucci-Ponzano B, Mazzone M, Rossi M, Moracci M. 2005. Probing the catalytically essential residues of the alpha-L-fucosidase from the hyperthermophilic archaeon Sulfolobus solfataricus. Biochemistry 44:6331–6342.
- Cobucci-Ponzano B, Conte F, Benelli D, Londei P, Flagiello A, Monti M, . 2006. The gene of an archaeal alpha-l-fucosidase is expressed by translational frameshifting. Nucleic Acids Res 34:4258–4268.
- Cobucci-Ponzano B, Conte F, Mazzone M, Bedini E, Corsaro MM, Rossi M, Moracci M. 2008. Design of new reaction conditions for characterization of a mutant thermophilic α-l-fucosidase. Biocat Biotrans 26:18–24.
- Cobucci-Ponzano B, Conte F, Bedini E, Corsaro MM, Parrilli M, Sulzenbacher G, . 2009. β-Glycosyl azides as substrates for α-glycosynthases: preparation of efficient α-l-fucosynthases. Chem Biol 16:1097–1108.
- Cobucci-Ponzano B, Zorzetti C, Strazzulli A, Carillo S, Bedini E, Corsaro MM, . 2011. A novel alpha-d-galactosynthase from Thermotoga maritima converts beta-d-galactopyranosyl azide to alpha-galacto-oligosaccharides. Glycobiology 21:448–456.
- Comfort DA, Bobrov KS, Ivanen DR, Shabalin KA, Harris JM, Kulminskaya AA, Brumer H, Kelly RM. 2007. Biochemical analysis of Thermotoga maritima GH36 α-galactosidase TmGalA confirms the mechanistic commonality of clan GH-D glycoside hydrolases. Biochemistry 46:3319–3330.
- Demchenko AV, Rousson E, Boons GJ. 1999. Stereoselective 1,2-cis-galactosylation assisted by remote neighboring group participation and solvent effects. Tetrahedron Lett 40:6523–6526.
- Ducros VM, Tarling CA, Zechel DL, Brzozowski AM, Frandsen TP, von Ossowski I, . 2003. Anatomy of glycosynthesis: structure and kinetics of the Humicola insolens Cel7B E197A and E197S glycosynthase mutants. Chem Biol 10:619–628.
- Fialová P, Carmona AT, Robina I, Ettrich R, Sedmera P, Přikrylová V, Hušáková L, Křen V. 2005. Glycosyl azides – novel substrates for enzymatic transglycosylations. Tetrahedron Lett 46:8715–8718.
- Fukase K, Nakai Y, Kanoh T, Kusumoto S. 1998. Mild but efficient methods for stereoselective glycosylation with thioglycosides: activation by [N-phenylselenophthalimide-Mg(ClO4)2] and [PhIO-Mg(ClO4)2]. Synlett 1998:84–86.
- Galili U. 2001. The α-gal epitope Galα1-3Galβ1-4GlcNAc-R in xenotransplantation. Biochimie 83:557–563.
- Hada N, Oka J, Nishiyama A, Takeda T. 2006. Stereoselective synthesis of 1,2-cis galactosides: Synthesis of a glycolipid containing Galα1-6Gal component from Zygomycetes species. Tetrahedron Lett 47:6647–6650.
- Hancock SM, Vaughan M, Withers SG. 2006. Engineering of glycosidases and glycosyltransferases. Curr Opin Chem Biol 10:509–519.
- Imamura A, Ando H, Korogi S, Tanabe G, Muraoka O, Ishida H, Kiso M. 2003. Di-tert-butylsilylene DTBS group-directed α-selective galactosylation unaffected by C-2 participating functionalities. Tetrahedron Lett 44:6725–6728.
- Juaristi E, Cuevas G. 1992. Recent studies of the anomeric effect. Tetrahedron 48:5019–5087.
- Kim YW, Lee SS, Warren RA, Withers SG. 2004. Directed evolution of a glycosynthase from Agrobacterium sp. increases its catalytic activity dramatically and expands its substrate repertoire. J Biol Chem 279:42787–42793.
- Lin H, Tao H, Cornish VW. 2004. Directed evolution of a glycosynthase via chemical complementation. J Am Chem Soc 126:15051–15059.
- Ly HD, Withers SG. 1999. Mutagenesis of glycosidases. Annu Rev Biochem 68:487–522.
- Ma B, Simala-Grant JL, Taylor DE. 2006. Fucosylation in prokaryotes and eukaryotes. Glycobiology 16:158R–184R.
- Macher BA, Galili U. 2008. The Galα1,3Galβ1,4GlcNAc-R α-Gal epitope: a carbohydrate of unique evolution and clinical relevance. BBA Gen Subjects 1780:75–88.
- Mackenzie LF, Wang Q, Warren RAJ, Withers SG. 1998. Glycosynthases: mutant glycosidases for oligosaccharide synthesis. J Am Chem Soc 120:5583–5584.
- Malet C, Planas A. 1998. From beta-glucanase to beta-glucansynthase: glycosyl transfer to alpha-glycosyl fluorides catalyzed by a mutant endoglucanase lacking its catalytic nucleophile. FEBS Lett 440:208–212.
- Moracci M, Trincone A, Perugino G, Ciaramella M, Rossi M. 1998. Restoration of the activity of active-site mutants of the hyperthermophilic betaglycosidase from Sulfolobus solfataricus: dependence of the mechanism on the action of external nucleophiles. Biochemistry 37:17262–17270.
- Okuyama M, Mori H, Watanabe K, Kimura A, Chiba S. 2002. α-Glucosidase mutant catalyzes “α-glycosynthase”-type reaction. Biosci Biotechnol Biochem 66:928–933.
- Overend WG. 1972. In: Pigman W, Horton D, eds. Carbohydrate chemistry and biochemistry. New York: AP, P308.
- Perugino G, Trincone A, Rossi M, Moracci M. 2004. Oligosaccharide synthesis by glycosynthases. Trends Biotechnol 22:31–37.
- Perugino G, Cobucci-Ponzano B, Rossi M, Moracci M. 2005. Recent advances in the oligosaccharide synthesis promoted by catalytically engineered glycosidases. Adv Synth Catal 347:941–950.
- Rosano C, Zuccotti S, Cobucci-Ponzano B, Mazzone M, Rossi M, Moracci M, . 2004. Structural characterization of the nonameric assembly of an archaeal alpha-l-fucosidase by synchrotron small angle X-ray scattering. Biochem Biophys Res Commun 320:176–182.
- Shaikh FA, Withers SG. 2008. Teaching old enzymes new tricks: engineering and evolution of glycosidases and glycosyl transferases for improved glycoside synthesis. Biochem Cell Biol. 86:169–177.
- Sulzenbacher G, Bignon C, Nishimura T, Tarling CA, Withers SG, Henrissat B, Bourne Y. 2004. Crystal structure of Thermotoga maritima alpha-l-fucosidase. Insights into the catalytic mechanism and the molecular basis for fucosidosis. J Biol Chem 279:13119–13128.
- Tarling CA, He S, Sulzenbacher G, Bignon C, Bourne Y, Henrissat B, Withers SG. 2003. Identification of the catalytic nucleophile of the family 29 alpha-l-fucosidase from Thermotoga maritima through trapping of a covalent glycosyl-enzyme intermediate and mutagenesis. J Biol Chem 278:47394–47399.
- Vanhooren PT, Vandamme EJ. 1999. l-Fucose: occurrence, physiological role, chemical, enzymatic and microbial synthesis. J Chem Technol Biotechnol 74:479–497.
- Viladot JL, Canals F, Barllori X, Planas A. 2001. Long-lived glycosyl-enzyme intermediate mimic produced by formate re-activation of a mutant endoglucanase lacking its catalytic nucleophile Biochem J 355:79–86.
- Zhu X, Schmidt RR. 2009. New principles for glycoside-bond formation. Angew Chem Int Ed 48:1900–1934.