Enzymatic glycosyl transfer: Mechanisms and applications

Biocatalysis and Biotransformation

Volumn 29, Issue 1, 2011, Pages 1-18

  Desmet, Tom ^a   Soetaert, Wim ^a  

^a GHENT UNIVERSITY   (Belgium)

Author keywords

carbohydrate active enzymes; glycoside hydrolases; glycoside phosphorylases; glycosyl transferases; Glycosylation; transglycosidases

Indexed keywords

GLYCOSIDE HYDROLASES; GLYCOSYL; GLYCOSYL TRANSFERASE; GLYCOSYL TRANSFERASES; GLYCOSYLATED; GLYCOSYLATION REACTIONS; LOW-YIELD; PERSONAL CARE INDUSTRY; STRUCTURE-FUNCTION RELATIONSHIP; TRANSGLYCOSIDASES;

CATALYSTS; GLYCOSYLATION; ORGANIC COMPOUNDS; PHOSPHORYLATION; SUGARS;

ENZYMES;

BETA GALACTOSIDE; CYCLOMALTODEXTRIN GLUCANOTRANSFERASE; DEXTRANSUCRASE; GLYCOSIDASE; GLYCOSIDE; GLYCOSYLTRANSFERASE; LAMINARAN; LEVANSUCRASE; PHOSPHORYLASE; SUCRASE;

ARTICLE; BIOCATALYSIS; BIOCATALYST; CARBOHYDRATE METABOLISM; CRYSTAL STRUCTURE; ENZYME ACTIVITY; ENZYME DEGRADATION; ENZYME KINETICS; ENZYME MECHANISM; ENZYME SPECIFICITY; ENZYME SUBSTRATE; GLYCOSYLATION; PROTEIN ANALYSIS; PROTEIN PHOSPHORYLATION; PROTEIN STRUCTURE; PROTEIN TRANSPORT; STRUCTURE ACTIVITY RELATION;

EID: 79551509765     PISSN: 10242422     EISSN: 10292446     Source Type: Journal    
DOI: 10.3109/10242422.2010.548557     Document Type: Article

References (160)

1. Aisaka K, Masuda T, Chikamune T. 1996. Properties of maltose phosphorylase from Propionibacterium freudenreichii . J Ferment Bioeng 82:171-173.
2. Aisaka K, Masuda-Kato T, Chikamune T, Kamitori K, Uosaki Y, Saito Y. 2000. Enzymatic synthesis of novel disaccharides using disaccharide phosphorylases. J Biosci Bioeng 90:208-213.
3. Albenne C, Skov L, Mirza O, Gajhede M, Feller G, D ' Amico S, Andre G, Potocki-Veronese G, Van der Veen BA, Monsan P, Remaud-Simeon M. 2004. Molecular basis of the amylose-like polymer formation catalyzed by Neisseria polysaccharea amylosucrase. J Biol Chem 279:726-734.
4. Balogh T, Boross L, Kos á ry J. 2004. Novel reaction systems for the synthesis of O -glucosides by enzymatic reverse hydrolysis. Tetrahedron 60:679-682.
5. Beine R, Moraru R, Nimtz M, Na ' amnieh S, Pawlowski A, Buchholz K, Seibel J. 2008. Synthesis of novel fructooligosaccharides by substrate and enzyme engineering. J Biotechnol 138:33-41.
6. Benesova E, Lipovova P, Dvorakova H, Kralova B. 2010. β - D - Galactosidase from Paenibacillus thiaminolyticus catalyzing transfucosylation reactions. Glycobiology 20:442-451.
7. Bertrand A, Morel S, Lefoulon F, Rolland Y, Monsan P, Remaud- Simeon M. 2006. Leuconostoc mesenteroides glucansucrase synthesis of fl avonoid glucosides by acceptor reactions in aqueous - organic solvents. Carbohydr Res 341:855-863.
8. Blake CC, Koenig DF, Mair GA, North AC, Phillips DC, Sarma VR. 1965. Structure of hen egg-white lysozyme. A three-dimensional Fourier synthesis at 2 Angstrom resolution. Nature 206:757-761.
9. Bojarov á P, Kren V. 2009. Glycosidases: a key to tailored carbohydrates. Trends Biotechnol 27: 199-209.
10. Bowles D, Isayenkova J, Lim EK, Poppenberger B. 2005. Glycosyltransferases: managers of small molecules. Curr Opin Plant Biotechnol 8:254-263.
11. Buchholz K, Noll-Borchers M, Schwengers D. 1998. Production of leucrose by dextransucrase. Starch 50:164-172.
12. Cantarel BL, Coutinho PM, Rancurel C, Bernard T, Lombard V, Henrissat B. 2009. The Carbohydrate-Active EnZymes database (CAZy): an expert resource for glycogenomics. Nucleic Acids Res 37:D233-D238.
13. Cardini CE, Paladini AC, Caputto R, Leloir LF. 1950. Uridine diphosphate glucose: the coenzyme of the galactose - glucose phosphate isomerization. Nature 165:191-193.
14. Cerdobbel A, Desmet T, De Winter K, Maertens J, Soetaert W. 2010a. Increasing the thermostability of sucrose phosphorylase by multipoint covalent immobilization. J Biotechnol 150:125-130.
15. Cerdobbel A, De Winter K, Desmet T, Soetaert W. 2010b. Sucrose phosphorylase as cross-linked enzyme aggregate: improved thermal stability for industrial applications. Biotechnol J 5:1192-1197.
16. Chaen H, Nakada T, Nishimoto T, Kuroda N, Fukuda S, Sugimoto T, Kurimoto M, Tsujisaka Y. 1999. Purification and characterization of thermostable trehalose phosphorylase from Thermoanaerobacter brockii . J Appl Glycosci 46:399-405.
17. Champion E, Andre I, Moulis C, Boutet J, Descroix K, Morel S, Monsan P, Mulard LA, Remaud-Simeon M. 2009. Design of α -transglucosidases of controlled specificity for programmed chemoenzymatic synthesis of antigenic oligosaccharides. J Am Chem Soc 131:7379-7389.
18. Cobucci-Ponzano B, Conte F, Bedini E, Corsaro MM, Parrilli M, Sulzenbacher G, Lipski A, Dal Piaz F, Lepore L, Rossi M, Moracci M. 2009. β -Glycosyl azides as substrates for β -glycosynthases: preparation of efficient β - L -fucosynthases. Chem Biol 16:1097-1108.
19. Cote GL, Sheng S, Dunlap CA. 2008. Alternansucrase acceptor products. Biocatal Biotransformation 26:161-168.
20. Coutinho PM, Starn M, Blanc E, Henrissat B. 2003. Why are there so many carbohydrate-active enzyme-related genes in plants? Trends Plant Sci 8:563-565.
21. Crabb WD, Mitchinson C. 1997. Enzymes involved in the processing of starch to sugars. Trends Biotechnol 15:349-352.
22. Damian-Almazo JY, Moreno A, Lopez-Munguia A, Soberon X, Gonzalez-Munoz F, Saab-Rincon G. 2008. Enhancement of the alcoholytic activity of α -amylase AmyA from Thermotoga maritima MSB8 (DSM 3109) by site-directed mutagenesis. Appl Environ Microbiol 74:5168-5177.
23. Davies G, Henrissat B. 1995. Structures and mechanisms of glycosyl hydrolases. Structure 3:853-859.
24. Davies GJ, Wilson KS, Henrissat B. 1997. Nomenclature for sugar-binding subsites in glycosyl hydrolases. Biochem J 321:557-559.
25. De Groeve MR, De Baere M, Hofl ack L, Desmet T, Vandamme EJ, Soetaert W. 2009a. Creating lactose phosphorylase enzymes by directed evolution of cellobiose phosphorylase. Protein Eng Des Sel 22:393-399.
26. De Groeve MR, Depreitere V, Desmet T, Soetaert W. 2009b. Enzymatic production of α - D -galactose 1-phosphate by lactose phosphorolysis. Biotechnol Lett 31:1873-1877.
27. De Groeve MR, Remmery L, Van Hoorebeke A, Stout J, Desmet T, Savvides SN, Soetaert W. 2010a. Construction of cellobiose phosphorylase variants with broadened acceptor specificity towards anomerically substituted glucosides. Biotechnol Bioeng 107:413-420.
28. De Groeve MR, Tran GH, Van Hoorebeke A, Stout J, Desmet T, Savvides SN and Soetaert W. 2010b. Development and application of a screening assay for glycoside phosphorylases. Anal Biochem 401:162-167.
29. Del Valle MEMM. 2009. Cyclodextrins and their use: a review. Process Biochem 39:1033-1046.
30. Demuth K, Jordening HJ, Buchholz K. 2002. Oligosaccharide synthesis by dextransucrase: new unconventional acceptors. Carbohydr Res 337:1811-1820.
31. de Roode BM, Franssen MCR, Van der Padt A, Boom RM. 2003. Perspectives for the industrial enzymatic production of glycosides. Biotechnol Progr 19:1391-1402.
32. Deslongchamps P. 1993. Intramolecular strategies and stereoelectronic effects. Glycosides hydrolysis revisited. Pure Appl Chem 65:1161-1178.
33. Egloff MP, Uppenberg J, Haalck L, van Tilbeurgh H. 2001. Crystal structure of maltose phosphorylase from Lactobacillus brevis : unexpected evolutionary relationship with glucoamylases. Structure 9:689-697.
34. Eneyskaya EV, Sundqvist G, Golubev AM, Ibatullin FM, Ivanen DR, Shabalin KA, Brumer H, Kulminskaya AA. 2009. Transglycosylating and hydrolytic activities of the aβ -mannosidase from Trichoderma reesei . Biochimie 91:632-638.
35. Erb A, Weiss H, Haerle J, Bechthold A. 2009. A bacterial glycosyltransferase gene toolbox: generation and applications. Phytochemistry 70:1812-1821.
36. Feng HY, Drone J, Hoffman L, Tran V, Tellier C, Rabiller C, Dion M. 2005. Converting a β -glycosidase into a β -transglycosidase by directed evolution. J Biol Chem 280:37088-37097.
37. Fischer E. 1893. Ueber die glucoside der alkohole. Chem Ber 26:2400-2412.
38. Garc i a-Garibay M, Lopez-Munguia A, Barzana E. 2000. Alcoholysis and reverse hydrolysis reactions in organic one-phase system with a hyperthermophilic β -glycosidase. Biotechnol Bioeng 69: 627-632.
39. Gloster TM, Davies GJ. 2010. Glycosidase inhibition: assessing mimicry of the transition state. Org Biomol Chem 8:305-320.
40. Goedl C, Schwarz A, Minani A, Nidetzky B. 2007. Recombinant sucrose phosphorylase from Leuconostoc mesenteroides : characterization, kinetic studies of transglucosylation, and application of immobilised enzyme for production of α - D -glucose 1-phosphate. J Biotechnol 129:77-86.
41. Goedl C, Sawangwan T, Mueller M, Schwarz A, Nidetzky B. 2008a. A high-yielding biocatalytic process for the production of 2- O -( α - D -glucopyranosyl)- sn -glycerol, a natural osmolyte and useful moisturizing ingredient. Angew Chem Int Ed Engl 47:10086-10089.
42. Goedl C, Schwarz A, Mueller M, Brecker L, Nidetzky B. 2008b. Mechanistic differences among retaining disaccharide phosphorylases: insights from kinetic analysis of active site mutants of sucrose phosphorylase and α,α -trehalose phosphorylase. Carbohydr Res 343:2032-2040.
43. Goedl C, Sawangwan T, Wildberger P, Nidetzky B. 2010. Sucrose phosphorylase: a powerful transglucosylation catalyst for the synthesis of α - D -glucosides as industrial fine chemicals. Biocatal Biotransformation 28:10-21.
44. Goyal K, Kim BJ, Kim JD, Kim YK, Kitaoka M, Hayashi K. 2002. Enhancement of transglycosylation activity by construction of chimeras between mesophilic and thermophilic β -glucosidase. Arch Biochem Biophys 407:125-134.
45. Hancock SM, Vaughan MD, Withers SG. 2006. Engineering of glycosidases and glycosyltransferases. Curr Opin Chem Biol 10:509-519.
46. Hansson T, Kaper T, van der Oost J, de Vos WM, Adlercreutz P. 2001. Improved oligosaccharide synthesis by protein engineering of â -glucosidase CelB from hyperthermophilic Pyrococcus furiosus . Biotechnol Bioeng 73:203-210.
47. Heightman TD, Vasella AT. 1999. Recent insights into inhibition, structure and mechanism of configuration-retaining glycosidases. Angew Chem Int Ed Engl 38:751-770.
48. Hellmuth H, Wittrock S, Kralj S, Dijkhuizen L, Hofer B, Seibel J. 2008. Engineering the glucansucrase GTFR enzyme reaction and glycosidic bond specificity: toward tailor-made polymer and oligosaccharide products. Biochemistry 47:6678-6684.
49. Henrissat B. 1991. A classification of glycosyl hydrolases based on amino-acid sequence similarities. Biochem J 280:309-316.
50. 6 barrel fold. Structure 12:937-947.
51. Hidaka M, Nishimoto M, Kitaoka M, Wakagi T, Shoun H, Fushinobu S. 2009. The crystal structure of galacto- N -biose/ lacto- N -biose I phosphorylase: a large deformation of a TIM barrel scaffold. J Biol Chem 284:7273-7283.
52. Hinz SW, Doeswijk-Voragen CH, Schipperus R, Van den Broek LA, Vincken JP, Voragen AG. 2006. Increasing the transglycosylation activity of α -galactosidase from Bifidobacterium adolescentis DSM 20083 by site-directed mutagenesis. Biotechnol Bioeng 83:122-131.
53. Homann A, Seibel J. 2009. Towards tailor-made oligosaccharides - chemo-enzymatic approaches by enzyme and substrate engineering. Appl Microbiol Biotechnol 83:209-216.
54. Homann A, Biedendieck R, Gotze S, Jahn D, Seibel J. 2007. Insights into polymer versus oligosaccharide synthesis: mutagenesis and mechanistic studies of a novel levansucrase from Bacillus megaterium . Biochem J 407:189-198.
55. Honda Y, Kitaoka M. 2006. The first glycosynthase derived from an inverting glycoside hydrolase. J Biol Chem 281:1426-1431.
56. Honda Y, Fushinobu S, Hidaka M, Wakagi T, Shoun H, Taniguchi H, Kitaoka M. 2008. Alternative strategy for converting an inverting glycoside hydrolase into a glycosynthase. Glycobiology 18:325-220.
57. Hu Y, Luan H, Ge G, Liu H, Zhang Y, Zhou K, Liu Y, Yang L. 2009. Deoxynojirimycin enhanced the transglycosylation activity of a glycosidase from the China white jade snail. J Biotechnol 139:229-235.
58. Igura M, Maita N, Kamishikiryo J, Yamada M, Obita T, Maenaka K, Kohda D. 2008. Structure-guided identification of a new catalytic motif of oligosaccharyltransferase. EMBO J 27:234-243.
59. Jahn M, Marles J, Warren RA, Withers SG. 2003. Thioglycoligases: mutant glycosidases for thioglycoside synthesis. Angew Chem Int Ed Engl 42:352-354.
60. Jahn M, Chen H, M ü llegger J, Marles J, Warren RA, Withers SG. 2004. Thioglycosynthases: double mutant glycosidases that serve as scaffolds for thioglycoside synthesis. Chem Commun 7:274-275.
61. Johnson KF. 1999. Synthesis of oligosaccharides by bacterial enzymes. Glyconj J 16:141-146.
62. Johnson LN, Phillips DC. 1965. Structure of some crystalline lysozyme - inhibitor complexes determined by X-ray analysis at 6 Angstrom resolution. Nature 206:761-763.
63. Jorgensen F, Hansen OC, Stougaard P. 2001. High-efficiency synthesis of oligosaccharides with a truncated α -galactosidase from Bifidobacterium bifidum . Appl Microbiol Biotechnol 57: 647-652.
64. Kang J, Kim YM, Kim N, Kim DW, Nam SH, Kim D. 2009. Synthesis and characterization of hydroquinone fructoside using Leuconostoc mesenteroides levansucrase. Appl Microbiol Biotechnol 83:1009-1016.
65. Kelly RM, Leemhuis H, Rozeboom HJ, van Oosterwijk N, Dijkstra BW, Dijkhuizen L. 2008. Elimination of competing hydrolysis and coupling side reactions of a cyclodextrin glucanotransferase by directed evolution. Biochem J 413:517-525.
66. Kelly RM, Dijkhuizen L, Leemhuis H. 2009. Starch and α -glucan acting enzymes, modulating their properties by directed evolution. J Biotechnol 140:184-193.
67. Kim MI, Kim HS, Jung J, Rhee S. 2008. Crystal structures and mutagenesis of sucrose hydrolase from Xanthomonas axonopodis pv. glycines: insight into the exclusively hydrolytic amylosucrase fold. J Mol Biol 380:636-647.
68. Kim YW, Lovering AL, Chen HM, Kantner T, McIntosh LP, Strynadka NCJ, Withers SG. 2006. Expanding the thioglycoligase strategy to the synthesis of α -linked thioglycosides allows structural investigation of the parent enzyme/substrate complex. J Am Chem Soc 128:2202-2203.
69. Kitao S, Sekine H. 1994a. α - D -Glucosyl transfer to phenolic compounds by sucrose phosphorylase from Leuconostoc mesenteroides and production of α -arbutin. Biosci Biotechnol Biochem 58:38-42.
70. Kitao S, Sekine H. 1994b. Syntheses of two kojic acid glucosides with sucrose phosphorylase from Leuconostoc mesenteroides . Biosci Biotechnol Biochem 58:419-420.
71. Kitao S, Ariga T, Matsuda T, Sekine H. 1993. The syntheses of catechin glucosides by transglycosylation with Leuconostoc mesenteroides sucrose phosphorylase. Biosci Biotechnol Biochem 57:2010-2015.
72. Kitao S, Matsudo T, Sekine H. 1995. Enzymatic syntheses of two stable ( - )-epigallocatechin gallate-glucosides by sucrose phosphorylase. Biosci Biotechnol Biochem 59:2167-2169.
73. Kitao S, Matsudo T, Sasaki T, Koga T, Kawamura M. 2000. Enzymatic synthesis of stable, odorless, and powdered furanone glucosides by sucrose phosphorylase. Biosci Biotechnol Biochem 64:134-141.
74. Kitaoka M, Hayashi K. 2002. Carbohydrate-processing phosphorolytic enzymes. Trends Glycosci Glycotechnol 14:35-50.
75. Kittl R, Withers S. 2010. New approaches to enzymatic glycoside synthesis through directed evolution. Carbohydr Res 345: 1272-1279.
76. Knowles JR. 1980. Enzyme-catalyzed phosphoryl transfer reactions. Annu Rev Biochem 49:877-919.
77. Kone FMT, Le Bechec M, Sine JP, Dion M, Tellier C. 2009. Digital screening methodology for the directed evolution of transglycosidases. Protein Eng Des Sel 22:37-44.
78. Kralj S, Buchholz K, Dijkhuizen L, Seibel J. 2008. Fructansucrase enzymes and sucrose analogues: a new approach for the synthesis of unique fructo-oligosaccharides. Biocatal Biotransformation 26:32-41.
79. Kren V. 2008. Glycoside vs. aglycon: the role of glycosidic residue in biological activity. In: Fraser-Reid B, Tatsuta K, Thiem J, editors. Glycoscience. Berlin: Springer. pp 2589 - 2644.
80. Kren V, Thiem J. 1997. Glycosylation employing bio-systems: from enzymes to whole cells. Chem Soc Rev 26:463-473.
81. Kwon T, Kim CT, Lee JH. 2007. Transglucosylation of ascorbic acid to ascorbic acid 2-glucoside by a recombinant sucrose phosphorylase from Bifidobacterium longum . Biotechnol Lett 29:611-615.
82. Laine RA. 1994. A calculation of all possible oligosaccharide isomers both branched and linear yields 1.05 × 10 12 structures for a reducing hexasaccharide: the isomer barrier to development of single-method saccharide sequencing or synthesis systems. Glycobiology 4:759-767.
83. Lairson LL, Withers SG. 2004. Mechanistic analogies amongst carbohydrate modifying enzymes. Chem Commun 20: 2243-2248.
84. Lairson LL, Henrissat B, Davies GJ, Withers SG. 2008. Glycosyltransferases: structures, functions, and mechanisms. Annu Rev Biochem 77:521-555.
85. Lee SG, Lee JO, Yi JK, Kim BG. 2002. Production of cytidine 5′ -monophosphate N -acetylneuraminic acid using recombinant Escherichia coli as a biocatalyst. Biotechnol Bioeng 80:516-524.
86. Leemhuis H, Kelly RM, Dijkhuizen L. 2010. Engineering of cyclodextrin glucanotransferases and the impact for biotechnological applications. Appl Microbiol Biotechnol 85:823-825.
87. Lehman J. 1998. Carbohydrates: structure and biology. Stuttgart: Thieme.
88. Lim EK, Ashford DA, Hou B, Jackson RG, Bowles DJ. 2004. Arabidopsis glycosyltransferases as biocatalysts in fermentation for regioselective synthesis of diverse quercetin glucosides. Biotechnol Bioeng 87:623-631.
89. Liu J, Mushegian A. 2003. Three monophyletic superfamilies account for the majority of the known glycosyltransferases. Protein Sci 12:1418-1431.
90. Luzhetskyy A, Bechthold A. 2008. Features and applications of bacterial glycosyltransferases: current state and prospects. Appl Microbiol Biotechnol 80:945-952.
91. Maiorano AE, Piccoli RM, da Silva ES, de Andrade Rodrigues MF. 2008. Microbial production of fructosyltransferases for synthesis of pre-biotics. Biotechnol Lett 30:1867-1877.
92. Maita N, Nyirenda J, Igura M, Kamishikiryo J, Kohda D. 2010. Comparative structural biology of eubacterial and archaeal oligosaccharyltransferases. J Biol Chem 285:4941-4950.
93. Makowski K, Bialkowska A, Kur J, Turkiewicz M. 2009. Antarctic, cold-adapted β -galactosidase of Pseudoalteromonas sp. 22b as an effective tool for alkyl galactopyranosides synthesis. Enzyme Microb Technol 44:59-64.
94. Martearena MR, Daz M, Ellenrieder G. 2008. Synthesis of rutinosides and rutinose by reverse hydrolysis catalyzed by fungal α - L -rhamnosidases. Biocatal Biotransformation 26:177-185.
95. Masada S, Kawase Y, Nagatoshi M, Oguchi Y, Terasaka K, Mizukami H. 2007. An efficient chemoenzymatic production of small molecule glucosides with in situ UDP-glucose recycling. FEBS Lett 581:2562-2566.
96. Meng G, Futterer K. 2003. Structural framework of fructosyltransfer in Bacillus subtilis levansucrase. Nature Struct Biol 10:935-941.
97. Meulenbeld GH, Hartmans S. 2000. Transglycosylation by Streptococcus mutans GS-5 glucosyltransferase-D: acceptor specificity and engineering of reaction conditions. Biotechnol Bioeng 70:363-369.
98. Michaud P, Da Costa A, Courtois B, Courtois J. 2003. Polysaccharide lyases: recent developments as biotechnological tools. Crit Rev Biotechnol 23:233-266.
99. Mieyal JJ, Simon M, Abeles RH. 1972. Mechanism of action of sucrose phosphorylase. 3. The reaction with water and other alcohols. J Biol Chem 247:532-542.
100. Mirza O, Skov LK, Sprogoe D, van den Broek LA, Beldman G, Kastrup JS, Gajhede M. 2006. Structural rearrangements of sucrose phosphorylase from Bifidobacterium adolescentis during sucrose conversion. J Biol Chem 281:35576-35584.
101. Monsan P, Ouarne F. 2010. Oligosaccharides derived from sucrose. In: Chalarampopoulos D, Ratstall RA, editors. Prebiotics and probiotics science and technology. Berlin: Springer. pp 293 - 336.
102. Monsan P, Remaud-Simeon M, Andre I. 2010. Transglucosidases as efficient tools for oligosaccharide and glucoconjugate synthesis. Curr Opin Microbiol 13:293-300
103. Moon YH, Kim G, Lee JH, Jin XJ, Kim DW, Kim D. 2006. Enzymatic synthesis and characterization of novel epigallocatechin gallate glucosides. J Mol Catal B Enzym 40:1-7.
104. Moon YH, Lee JH, Jhon DY, Jun WJ, Kang SS, Sim J, Choi H, Moon JH, Kim D. 2007. Synthesis and characterization of novel quercetin- α - D -glucopyranosides using glucansucrase from Leuconostoc mesenteroides . Enzyme Microb Technol 40:1124-1129.
105. Moulis C, Joucla G, Harrison D, Fabre E, Potocki-Veronese G, Monsan P, Remaud-Simeon M. 2006. Understanding the polymerization mechanism of glycoside-hydrolase family 70 glucansucrases. J Biol Chem 281:31254-31267.
106. Moulis C, Vaca-Medina G, Suwannarangsee S, Monsan P, Potocki-Veronese G, Remaud-Simeon M. 2008. One-step synthesis of isomaltooligosaccharide syrups and dextrans of controlled size using engineered dextransucrase. Biocatal Biotransformation 26:141-151.
107. Mueller M, Nidetzky B. 2007. The role of Asp-295 in the catalytic mechanism of Leuconostoc mesenteroides sucrose phosphorylase probed with site-directed mutagenesis. FEBS Lett 581: 1403-1408.
108. Mullegger J, Chen HM, Chan WY, Reid SP, Jahn M, Warren RAJ, Salleh HM, Withers SG. 2006. Thermostable glycosynthases and thioglycoligases derived from Thermotoga maritima β - glucuronidase. Chembiochem 7:1028-1030.
109. Nashiru O, Zechel DL, Stoll D, Mohammadzadeh T, Warren RA, Withers SG. 2001. β -Mannosynthase: synthesis of β - mannosides with a mutant β -mannosidase. Angew Chem Int Ed Engl 40:417-420.
110. Nerinckx W, Desmet T, Claeyssens M. 2003. A hydrophobic platform as a mechanistically relevant transition state stabilising factor appears to be present in the active centre of all glycoside hydrolases. FEBS Lett 538:1-7.
111. Nerinckx W, Desmet T, Piens K, Claeyssens M. 2005. An elaboration on the syn - anti proton donor concept of glycoside hydrolases: electrostatic stabilisation of the transition state as a general strategy. FEBS Lett 579:302-312.
112. Nerinckx W, Desmet T, Claeyssens M. 2006. Itineraries of enzymatically and non-enzymatically catalyzed substitutions at O -glycopyranosidic bonds. Arkivoc 90-116.
113. Nicolaou KC, Mitchell HJ. 2001. Adventures in carbohydrate chemistry: new synthetic technologies, chemical synthesis, molecular design, and chemical biology. Angew Chem Int Ed Engl 40:1576-1624.
114. Nomura K, Sugimoto K, Nishiura H, Ohdan K, Nishimura T, Hayashi H, Kuriki T. 2008. Glucosylation of acetic acid by sucrose phosphorylase. Biosci Biotechnol Biochem 72:82-87.
115. Okada H, Fukushi E, Onodera S, Nishimoto T, Kawabata J, Kikuchi M, Shiomi N. 2003. Synthesis and structural analysis of five novel oligosaccharides prepared by glucosyltransfer from β - D -glucose 1-phosphate to isokestose and nystose using Thermoanaerobacter brockii kojibiose phosphorylase. Carbohydr Res 338:879-885.
116. Ortiz-Soto ME, Rivera M, Rudino-Pinera E, Olvera C, Lopez-Munguia AL. 2008. Selected mutations in Bacillus subtilis levansucrase semi-conserved regions affecting its biochemical properties. Protein Eng Des Sel 21:589-595.
117. Osanjo G, Dion M, Drone J, Solleux C, Tran V, Rabiller C, Tellier C. 2007. Directed evolution of the α - L -fucosidase from Thermotoga maritima into an α - L -transfucosidase. Biochemistry 46:1022-1033.
118. Palcic MM. 1999. Biocatalytic synthesis of oligosaccharides. Curr Opin Biotechnol 10:616-624.
119. Percy A, Ono H, Hayashi K. 1998. Acceptor specificity of cellobiose phosphorylase from Cellvibrio gilvus : synthesis of three branched trisaccharides. Carbohydr Res 308:423-429.
120. Persson K, Ly HD, Dieckelmann M, Wakarchuck WW, Withers SG, Strynadka NC. 2001. Crystal structure of the retaining galactosyltransferase LgtC from Neisseria meningitidis in complex with donor and acceptor sugar analogs. Nature Struct Biol 8:98-100.
121. 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.
122. Piens K, Stahlberg J, Nerinckx W, Teeri TT, Claeyssens M. 2004. Structure - reactivity studies of Trichoderma reesei cellobiohydrolase Cel7A. In: Saha BC, Hayashi K, editors. Lignocellulose biodegradation. ACS publications, Washington DC, USA. pp. 207 - 226.
123. Placier G, Watzlawick H, Rabiller C, Mattes R. 2009. Evolved β -galactosidases from Geobacillus stearothermophilus with improved transgalactosylation yield for galacto-oligosaccharide production. Appl Environ Microbiol 75:6312-6321.
124. Plam D, Klein H, Schninzel R, Buehner M, Helmreich E. 1990. The role of pyridoxal 5′ -phosphate in glycogen phsophorylase catalysis. Biochemistry 29:1099-1107.
125. Remaud-Simeon M, Willemot RM, Sarcabal P, de Montalk GP, Monsan P. 2000. Glucansucrases: molecular engineering and oligosaccharide synthesis. J Mol Catal B Enzym 10:117-128.
126. Robyt JF, Yoon SH, Mukerjea R. 2008. Dextransucrase and the mechanism for dextran biosynthesis. Carbohydr Res 343: 3039-3048.
127. Rose JK, Braam J, Fry SC, Nishitani K. 2002. The XTH family of enzymes involved in xyloglucan endotransglucosylation and endohydrolysis: current perspectives and a new unifying nomenclature. Plant Cell Physiol 43:1421-1435.
128. Rye CS, Withers SG. 2000. Glycosidase mechanisms. Curr Opin Chem Biol 4:573-580.
129. Sammut SJF, Finn RD, Bateman A. 2008. Pfam 10 years on: 10 000 families and still growing. Brief Bioinform 9:210-219.
130. Schneider J, Fricke C, Overwin H, Hofmann B, Hofer B. 2009. Generation of amylosucrase variants that terminate catalysis of acceptor elongation at the di- or trisaccharide stage. Appl Environ Microbiol 75:7453-7460.
131. Seibel J, Jordening HJ, Buchholz K. 2006. Glycosylation with activated sugars using glycosyltransferases and transglycosidases. Biocatal Biotransformation 24:311-342.
132. Seo ES, Lee JH, Park JY, Kim D, Han HJ, Robyt JF. 2005. Enzymatic synthesis and anti-coagulant effect of salicin analogs by using the Leuconostoc mesenteroides glucansucrase acceptor reaction. J Biotechnol 117:31-38.
133. 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.
134. Shin MH, Cheong NY, Lee JH, Kim KH. 2009. Transglucosylation of caffeic acid by a recombinant sucrose phosphorylase in aqueous buffer and aqueous - supercritical CO 2 media. Food Chem 115:1028-1033.
135. Sinnott ML. 1994. Catalytic mechanisms of enzymic glycosyl transfer. Chem Rev 90:1171-1202.
136. Stern R, Jedrzejas MJ. 2008. Carbohydrate polymers at the center of life ' s origins: the importance of molecular processivity. Chem Rev 108:5061-5085.
137. Sugimoto K, Nomura K, Nishiura H, Ohdan K, Ohdan K, Hayashi H, Kuriki T. 2007. Novel transglucosylating reaction of sucrose phosphorylase to carboxylic compounds such as benzoic acid. J Biosci Bioeng 104:22-29.
138. Tolborg JF, Petersen L, Jensen KJ, Mayer C, Jakeman DL, Warren RAJ, Withers SG. 2002. Solid-phase oligosaccharide and glycopeptide synthesis using glycosynthases. J Org Chem 67:4143-4149.
139. van Hijum S, Kralj S, Ozimek LK, Dijkhuizen L, van Geel-Schutten IGH. 2006. Structure - function relationships of glucansucrase and fructansucrase enzymes from lactic acid bacteria. Microbiol Mol Biol Rev 70:157-176.
140. van Rantwijk F, Woudenberg-van Oosterom M, Sheldon RA. 1999. Glycosidase-catalysed synthesis of alkyl glycosides. J Mol Catal B Enzym 6:511-532.
141. Varki A. 1993. Biological role of oligosaccharides: all of the theories are correct. Glycobiology 3:97-130.
142. Vaughan MD, Johnson K, Defrees S, Tang XP, Warren RAJ, Withers SJ. 2006. Glycosynthase-mediated synthesis of glycosphingolipids. J Am Chem Soc 128:6300-6301.
143. Vocadlo DJ, Davies GJ. 2008. Mechanistic insights into glycosidase chemistry. Curr Opin Chem Biol 12:539-555.
144. Vocadlo DJ, Davies GJ, Laine R, Withers SG. 2001. Catalysis by hen egg-white lysozyme proceeds via a covalent intermediate. Nature 412:835-838.
145. Vuong TV, Wilson DB. 2010. Glycoside hydrolases: catalytic base/ nucleophile diversity. Biotechnol Bioeng 107:195-205.
146. Wada J, Honda Y, Nagae M, Kato R, Wakatsuki S, Katayama T, Taniguchi H, Kumagai H, Kitaoka M, Yamamoto K. 2008. 1,2- α - L -Fucosynthase: a glycosynthase derived from an inverting α -glycosidase with an unusual reaction mechanism. FEBS Lett 582:3739-3743.
147. Wang X. 2009. Structure, mechanism and engineering of plant natural product glycosyltransferases. FEBS Lett 583: 3303-3309.
148. Watanabe H, Higashiyama T, Aga H, Nishimoto T, Kubota M, Fukuda S, Kurimoto M, Tsujisaka Y. 2005. Enzymatic synthesis of a 2- O - α - D -glucopyranosyl cyclic tetrasaccharide by kojibiose phosphorylase. Carbohydr Res 340:449-454.
149. Watson KA, McCleverty C, Geremia S, Cottaz S, Driguez H, Johnson LN. 1999. Phosphorylase recognition and phosphorolysis of its oligosaccharide substrate: answers to a long outstanding question. EMBO J 18:4619-4632.
150. Webb EC. 1992. Enzyme nomenclature. San Diego (CA): Academic Press.
151. Weijers CAGM, Franssen MCR, Visser GM. 2008. Glycosyltransferase- catalyzed synthesis of bioactive oligosaccharides. Biotechnol Adv 26:436-456.
152. Weinhausel A, Nidetzky B, Kysela C, Kulbe KD. 1995. Application of Escherichia coli maltodextrin-phosphorylase for the continuous production of glucose-1-phosphate. Enzyme Microb Technol 17:140-146.
153. Wiesbauer J, Goedl C, Schwarz A, Brecker L, Nidetzky B. 2009. Substitution of the catalytic acid - base Glu237 by Gln suppresses hydrolysis during glucosylation of phenolic acceptors catalyzed by Leuconostoc mesenteroides sucrose phosphorylase. J Mol Catal B Enzym 65:24-29.
154. Williams GJ, Zhang C, Thorson JS. 2007. Expanding the promiscuity of natural-product glycosyltransferase by directed evolution. Nature Chem Biol 3:657-662.
155. Williams GJ, Gantt RW, Thorson JS. 2008. The impact of enzyme engineering upon natural product glycodiversification. Curr Opin Chem Biol 12:556-564.
156. Wolfenden R, Lu X, Young G. 1998. Spontaneous hydrolysis of glycosides. J Am Chem Soc 120:6814-6815.
157. Yang M, Proctor MR, Bolam DN, Errey JC, Field RA, Gilbert HJ, Davis BG. 2005. Probing the breadth of macrolide glycosyltransferases: in vitro remodelling of a polyketide antibiotic creates active bacterial uptake and enhances potency. J Am Chem Soc 127:9336-9337.
158. Yang M, Davies GJ, Davis BG. 2007. A glycosynthase catalyst for the synthesis of fl avonoid glycosides. Angew Chem Int Ed Engl 46:3885-3888.
159. Yip VL, Withers SG. 2006. Breakdown of oligosaccharides by the process of elimination. Curr Opin Chem Biol, 10:147-155.
160. Zhang C, Griffith BR, Fu Q, Albermann C, Fu X, Lee IK, Li L, Thorson JS. 2006. Exploiting the reversibility of natural product glycosyltransferase- catalyzed reactions. Science 313:1291-1294.