Enzymatic Approaches to O-Glycoside Introduction: Glycosidases

Comprehensive Glycoscience: From Chemistry to Systems Biology

Volumn 1-4, Issue , 2007, Pages 453-487

  Bojarova Fialova P ^a   Kren V ^a  

^a INSTITUTE OF MATHEMATICS   (Czech Republic)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 78649903099     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1016/B978-044451967-2/00013-1     Document Type: Chapter

References (357)

1. Boons G.-J. Tetrahedron 1996, 52:1095-1121.
2. Seeberger P.H., Haase W.-C. Chem. Rev. 2000, 100:4349-4393.
3. Gridley J.J., Osborn H.M.I. J. Chem. Soc., Perkin Trans. 1, 2000, 1471-1491.
4. Nicolaou K.C., Hummel C.W., Iwabuchi Y. J. Am. Chem. Soc. 1992, 114:3126-3128.
5. Davies G.J., Charnock S.J., Henrissat B. Trends Glycosci. Glycotechnol. 2001, 13:105-120.
6. Palcic M.M. Curr. Opin. Biotechnol. 1999, 10:616-624.
7. Öhrlein R. Glycosyltransferase-Catalyzed Synthesis of Non-Natural Oligosaccharides. Biocatalysis - From Discovery to Application 1999, 227-254. Springer-Verlag, Berlin/ Heidelberg, Topics in Current Chemistry 200. W.-D. Fessner (Ed.).
8. Hill A.C. J. Chem. Soc., Trans. 1898, 73:634-658.
9. Fischer E. Ber. Dtsch. Chem. Ges. 1894, 27:2985-2993.
10. Bourquelot E., Bridel M. Ann. Chim. Phys. (Paris) 1913, 29:145-218.
11. Nelson J.M., Griffin E.G. J. Am. Chem. Soc. 1916, 38:1109-1115.
12. Edelman J. Adv. Enzymol. 1956, 17:189-232.
13. Pan S.C., Nicholson L.W., Kolachov P. J. Am. Chem. Soc. 1951, 73:2547-2550.
14. Pazur J.H., French D. J. Biol. Chem. 1952, 196:265-272.
15. Buston H.W., Jabbar A. Biochim. Biophys. Acta 1954, 15:543-548.
16. Courtois J.E., Petek F. Bull. Soc. Chim. Biol. 1957, 39:715-723.
17. Pazur J.H. Science 1953, 117:355-356.
18. Yamamoto K. J. Biochem. (Tokyo) 1973, 73:631-635.
19. Yamamoto K. J. Biochem. (Tokyo) 1973, 73:749-753.
20. Mega T., Ikenaka T., Matsushima Y. J. Biochem. (Tokyo) 1972, 71:107-114.
21. Akasaki M., Suzuki M., Funakoshi I., Yamashina I. J. Biochem. (Tokyo) 1976, 80:1195-1200.
22. Nilsson K.G.I. Carbohydr. Res. 1987, 167:95-103.
23. Nilsson K.G.I. Carbohydr. Res. 1988, 180:53-59.
24. Ajisaka K., Nishida H., Fujimoto H. Biotechnol. Lett. 1987, 9:243-248.
25. Ajisaka K., Nishida H., Fujimoto H. Biotechnol. Lett. 1987, 9:387-392.
26. Johansson E., Hedbys L., Larsson P.-O., Mosbach K., Gunnarsson A., Svensson S. Biotechnol. Lett. 1986, 8:421-424.
27. Hedbys L., Johansson E., Mosbach K., Larsson P.-O., Gunnarsson A., Svensson S., Lönn H. Glycoconjugate J. 1989, 6:161-168.
28. Bucke C., Rastall R.A. Chem. Br. 1990, 26:675-678.
29. Crout D.H.G., MacManus D.A. J. Chem. Soc., Perkin Trans. 1, 1990, 1865-1868.
30. Vic G., Crout D.H.G. Tetrahedron: Asymmetry 1994, 5:2513-2516.
31. Henrissat B. Biochem. J. 1991, 280:309-316.
32. Coutinho P.M., Henrissat B. 1999 Carbohydrate-Active Enzymes server at URL. http://afmb.cnrs-mrs.fr/CAZY/.
33. Yamamoto K., Takegawa K. Trends Glycosci. Glycotechnol. 1997, 9:339-354.
34. Fan J.-Q., Takegawa K., Iwahara S., Kondo A., Kato I., Abeygunawardana C., Lee Y.C. J. Biol. Chem. 1995, 270:17723-17729.
35. Trimble R.B., Atkinson P.H., Tarentino A.L., Plummer T.H., Maley F., Tomer K.B. J. Biol. Chem. 1986, 261:12000-12005.
36. Haneda K., Inazu T., Yamamoto K., Kumagai H., Nakahara Y., Kobata A. Carbohydr. Res. 1996, 292:61-70.
37. Deras I.L., Takegawa K., Kondo A., Kato I., Lee Y.C. Bioorg. Med. Chem. Lett. 1998, 8:1763-1766.
38. Bardales R.M., Bhavanandan V.P. J. Biol. Chem. 1989, 264:19893-19897.
39. Li Y.-T., Carter B.Z., Rao B.N.N., Schweingruber H., Li S.-C. J. Biol. Chem. 1991, 266:10723-10726.
40. Sasaki A., Ishimizu T., Geyer R., Hase S. FEBS J. 2005, 272:1660-1668.
41. Davies G., Henrissat B. Structure 1995, 3:853-859.
42. Tomme P., Kwan E., Gilkes N.R., Kilburn D.G., Warren R.A.J. J. Bacteriol. 1996, 178:4216-4223.
43. Johansson E., Hedbys L., Mosbach K., Larsson P.-O., Gunnarsson A., Svensson S. Enzyme Microb. Technol. 1989, 11:347-352.
44. Rajnochová E., Dvořáková J., Huňková Z., Křen V. Biotechnol. Lett. 1997, 19:869-872.
45. Vic G., Thomas D., Crout D.H.G. Enzyme Microb. Technol. 1997, 20:597-603.
46. Gelo-Pujic M., Guibé-Jampel E., Loupy A., Trincone A. J. Chem. Soc., Perkin Trans. 1, 1997, 1001-1002.
47. Křen V., Rajnochová E., Huňková Z., Dvořáková J., Sedmera P. Tetrahedron Lett. 1998, 39:9777-9780.
48. Meulenbeld G.H., De Roode B.M., Hartmans S. Biocatal. Biotrans. 2002, 20:251-256.
49. Rabaté M.J. Bull. Soc. Chim. Biol. 1935, 17:572-601.
50. Fortun Y., Colas B. Biotechnol. Lett. 1991, 13:863-866.
51. Spangenberg P., André C., Langlois V., Dion M., Rabiller C. Carbohydr. Res. 2002, 337:221-228.
52. Gill I., Valivety R. Angew. Chem., Int. Ed. Engl. 2000, 39:3804-3808.
53. Hedbys L., Larsson P.-O., Mosbach K., Svensson S. Biochem. Biophys. Res. Commun. 1984, 123:8-15.
54. McCarter J.D., Withers S.G. Curr. Opin. Struct. Biol. 1994, 4:885-892.
55. White A., Rose D.R. Curr. Opin. Struct. Biol. 1997, 7:645-651.
56. Ly H.D., Withers S.G. Annu. Rev. Biochem. 1999, 68:487-522.
57. Withers S.G. Carbohydr. Polym. 2001, 44:325-337.
58. Koshland D.E. Biol. Rev. 1953, 28:416-436.
59. Sinnott M.L. Chem. Rev. 1990, 90:1171-1202.
60. Legler G. Adv. Carbohydr. Chem. Biochem. 1990, 48:319-384.
61. Johnson L.N., Phillips D.C. Nature 1965, 206:761-763.
62. Phillips D.C. Proc. Natl. Acad. Sci. U.S.A. 1967, 57:484-495.
63. Lalégerie P., Legler G., Yon J.M. Biochimie 1982, 64:977-1000.
64. Cupples C.G., Miller J.H. Genetics 1988, 120:637-644.
65. Cupples C.G., Miller J.H., Huber R.E. J. Biol. Chem. 1990, 265:5512-5518.
66. Dale M.P., Ensley H.E., Kern K., Sastry K.A.R., Byers L.D. Biochemistry 1985, 24:3530-3539.
67. Dale M.P., Kopfler W.P., Chait I., Byers L.D. Biochemistry 1986, 25:2522-2529.
68. Martearena M.R., Blanco S., Ellenrieder G. Bioresource Technol. 2003, 90:297-303.
69. Kasumi T., Brewer C.F., Reese E.T., Hehre E.J. Carbohydr. Res. 1986, 146:39-49.
70. Ruiz J.M.J., Oßwald G., Petersen M., Fessner W.-D. J. Mol. Catal. B: Enzym. 2001, 11:189-197.
71. de Zoete M.C., van Rantwijk F., Sheldon R.A. Catal. Today 1994, 22:563-590.
72. Křen V., Thiem J. Chem. Soc. Rev. 1997, 26:463-473.
73. Werschkun B., König W.A., Křen V., Thiem J. J. Chem. Soc, Perkin Trans. 1, 1995, 2459-2466.
74. Gais H.-J., Zeissler A., Maidonis P. Tetrahedron Lett. 1988, 29:5743-5744.
75. Zarevúcka M., Vacek M., Kuldová J., Šaman D., Wimmer Z., Weignerová L., Křen V. Chirality 1999, 11:451-458.
76. Zarevúcka M., Wimmer Z., Rejzek M., Huňková Z., Křen V. Biotechnol. Lett. 2001, 23:1505-1515.
77. van Rantwijk F., Woudenberg-van Oosterom M., Sheldon R.A. J. Mol. Catal. B: Enzym. 1999, 6:511-532.
78. Thiem J., Sauerbrei B. Angew. Chem., Int. Ed. Engl. 1991, 30:1503-1505.
79. Ajisaka K., Fujimoto H., Isomura M. Carbohydr. Res. 1994, 259:103-115.
80. Tanaka H., Ito F., Iwasaki T. Biosci., Biotechnol., Biochem. 1995, 59:638-643.
81. Maru I., Ohta Y., Okamoto K., Suzuki S., Kakehi K., Tsukada Y. Biosci., Biotechnol., Biochem. 1992, 56:1557-1561.
82. Paris G., Ratier L., Amaya M.F., Nguyen T., Alzari P.M., Frasch A.C.C. J. Mol. Biol. 2005, 345:923-934.
83. Berthelot M. Compt. Rend. Hebdom. Seances Acad. Sci. (Paris) 1860, 50:980-984.
84. Bacon J.S.D., Edelman J. Arch. Biochem. 1950, 28:467-468.
85. Blanchard P.H., Albon N. Arch. Biochem. 1950, 29:220-222.
86. Andersen B., Thiesen N., Broe P.E. Acta Chem. Scand. 1969, 23:2367-2374.
87. Nakamura S., Miwa T. Nature 1964, 202:291.
88. Křen V. Biotechnol. Lett. 1992, 14:769-772.
89. Křen V., Svatoš A., Vaisar T., Havlícek V., Sedmera P., Pažoutová S., Šaman D. J. Chem. Res. 1993, 89.
90. Ajisaka K., Matsuo I., Isomura M., Fujimoto H., Shirakabe M., Okawa M. Carbohydr. Res. 1995, 270:123-130.
91. Singh S., Scigelova M., Crout D.H.G. Tetrahedron: Asymmetry 2000, 11:223-229.
92. Suwasono S., Rastall R.A. Biotechnol. Lett. 1996, 18:851-856.
93. Athanasopoulos V.I., Niranjan K., Rastall R.A. J. Mol. Catal. B: Enzym. 2004, 27:215-219.
94. Maitin V., Athanasopoulos V., Rastall R.A. Appl. Microbiol. Biotechnol. 2004, 63:666-671.
95. Prade H., Mackenzie L.F., Withers S.G. Carbohydr. Res. 1998, 305:371-381.
96. Taubken N., Thiem J. Glycoconjugate J. 1998, 15:757-767.
97. Scigelova M., Singh S., Crout D.H.G. J. Chem. Soc., Perkin Trans. 1, 1999, 777-782.
98. Nashiru O., Zechel D.L., Stoll D., Mohammadzadech T., Warren R.A.J., Withers S.G. Angew. Chem., Int. Ed. Engl. 2001, 40:417-420.
99. Jahn M., Stoll D., Warren R.A.J., Szabó L., Singh P., Gilbert H.J., Ducros V.M.-A., Davies G.J., Withers S.G. J. Chem. Soc., Chem. Commun. 2003, 1327-1329.
100. Svensson S.C.T., Thiem J. Carbohydr. Res. 1990, 200:391-402.
101. Murata T., Morimoto S., Zeng X., Watanabe S., Usui T. Carbohydr. Res. 1999, 320:192-199.
102. Ajisaka K., Shirakabe M. Carbohydr. Res. 1992, 224:291-299.
103. Vetere A., Galateo C., Paoletti S. Biochem. Biophys. Res. Commun. 1997, 234:358-361.
104. Ajisaka K., Fujimoto H., Miyasato M. Carbohydr. Res. 1998, 309:125-129.
105. Farkas E., Thiem J., Ajisaka K. Carbohydr. Res. 2000, 328:293-299.
106. Nilsson K.G.I., Eliasson A., Larsson-Lorek U. Biotechnol. Lett. 1995, 17:717-722.
107. Zhang J.-H., Dawes G., Stemmer W.P.C. Proc. Natl. Acad. Sci. U.S.A. 1997, 94:4504-4509.
108. Parikh M.R., Matsumura I. J. Mol. Biol. 2005, 352:621-628.
109. Zverlov V.V., Hertel C., Bronnenmeier K., Hroch A., Kellermann J., Schwarz W.H. Mol. Microbiol. 2000, 35:173-179.
110. Pozo M., Gotor V. J. Chem. Soc., Perkin Trans. 1, 1993, 1001-1002.
111. Rastall R.A., Rees N.H., Wait R., Adlard M.W., Bucke C. Enzyme Microb. Technol. 1992, 14:53-57.
112. Rastall R.A., Pikett S.F., Adlard M.W., Bucke C. Biotechnol. Lett. 1992, 14:373-378.
113. Ooi Y., Hashimoto T., Mitsuo N., Satoh T. Chem. Pharm. Bull. 1985, 33:1808-1814.
114. Binder W.H., Kählig H., Schmid W. Tetrahedron: Asymmetry 1995, 6:1703-1710.
115. Nieder V., Marx S.P., Gallego R.G., Kamerling J.P., Vliegenthart J.F.G., Elling L. J. Mol. Catal. B: Enzym. 2003, 21:157-166.
116. Scheckermann C., Wagner F., Fischer L. Enzyme Microb. Technol. 1997, 20:629-634.
117. Gunata Z., Vallier M.J., Sapis J.C., Baumes R., Bayonove C. Enzyme Microb. Technol. 1994, 16:1055-1058.
118. Křen V. Top. Curr. Chem. 1997, 186:45-63.
119. Křen V., Sedmera P., Havlícek V., Fišerová A. Tetrahedron Lett. 1992, 33:7233-7236.
120. Šigelová M., Křen V., Nilsson K.G.I. Biotechnol. Lett. 1994, 16:683-688.
121. Křen V., Šigelová M., Pikrylová V., Havlícek V., Sedmera P. Biocatalysis 1994, 10:181-193.
122. Johansson E., Hedbys L., Larsson P.-O. Enzyme Microb. Technol. 1991, 13:781-787.
123. Sauerbrei B., Thiem J. Tetrahedron Lett. 1992, 33:201-204.
124. Naundorf A., Ajisaka K. Enzyme Microb. Technol. 1999, 25:483-488.
125. Cantacuzène D., Attal S. Carbohydr. Res. 1991, 211:327-331.
126. Turner N.J., Webberley M.C. J. Chem. Soc., Chem. Commun. 1991, 1349-1350.
127. Ljunger G., Adlercreutz P., Mattiasson B. Enzyme Microb. Technol. 1994, 16:751-755.
128. Vic G., Hastings J.J., Crout D.H.G. Tetrahedron: Asymmetry 1996, 7:1973-1984.
129. Carrea G., Riva S. Angew. Chem., Int. Ed. Engl. 2000, 39:2226-2254.
130. Jahngen E.G.E., Lentz R.R., Pesheck P.S., Sackett P.H. J. Org. Chem. 1990, 55:3406-3409.
131. Panintrarux C., Adachi S., Matsuno R. Biotechnol. Lett. 1997, 19:899-902.
132. Fischer L., Bromann R., Kengen S.W.M., de Vos W.M., Wagner F. Nat. Biotechnol. 1996, 14:88-91.
133. Simerská P., Kuzma M., Pišvejcová A., Weignerová L., Macková M., Riva S., Křen V. Folia Microbiol. (Prague) 2003, 48:329-337.
134. Svasti J., Phongsak T., Sarnthima R. Biochem. Biophys. Res. Commun. 2003, 305:470-475.
135. Dintinger T., Dutheil-Bouëdec D., Bouchonneau M., Tellier C. Biotechnol. Lett. 1994, 16:689-692.
136. Nakano H., Shizuma M., Kiso T., Kitahata S. Biosci., Biotechnol., Biochem. 2000, 64:735-740.
137. Saito S., Tsuchiya T. Biochem. J. 1984, 222:829-832.
138. Nakano H., Murakami H., Shizuma M., Kiso T., de Araujo T.L., Kitahata S. Biosci., Biotechnol., Biochem. 2000, 64:1472-1476.
139. Stick R.V., Stubbs K.A. Tetrahedron: Asymmetry 2005, 16:321-335.
140. Jahn M., Marles J., Warren R.A.J., Withers S.G. Angew. Chem., Int. Ed. Engl. 2003, 42:352-354.
141. Fang J., Xie W., Li J., Wang P.G. Tetrahedron Lett. 1998, 39:919-922.
142. Singh S., Packwood J., Samuel C.J., Critchley P., Crout D.H.G. Carbohydr. Res. 1995, 279:293-305.
143. Hušáková L., Herkommerová-Rajnochová E., Semeuk T., Kuzma M., Rauvolfová J., Pikrylová V., Ettrich R., Plíhal O., Bezouška K., Křen V. Adv. Synth. Catal. 2003, 345:735-742.
144. Woudenberg-van Oosterom M., van Belle H.J.A., van Rantwijk F., Sheldon R.A. J. Mol. Catal. A: Chem. 1998, 134:267-274.
145. Horsch M., Mayer C., Sennhauser U., Rast D.M. Pharmacol. Ther. 1997, 76:187-218.
146. Kempton J.B., Withers S.G. Biochemistry 1992, 31:9961-9969.
147. Yasukochi T., Inaba C., Fukase K., Kusumoto S. Tetrahedron Lett. 1999, 40:6585-6589.
148. Chiffoleau-Giraud V., Spangenberg P., Rabiller C. Tetrahedron: Asymmetry 1997, 8:2017-2023.
149. Ballardie F.W., Capon B., Dearie W.M., Foster R.L. Carbohydr. Res. 1976, 49:79-92.
150. Williams S.J., Withers S.G. Carbohydr. Res. 2000, 327:27-46.
151. Yokoyama M. Carbohydr. Res. 2000, 327:5-14.
152. Hehre E.J., Brewer C.F., Genghof D.S. J. Biol. Chem. 1979, 254:5942-5950.
153. Hehre E.J., Matsui H., Brewer C.F. Carbohydr. Res. 1990, 198:123-132.
154. Viladot J.-L., Stone B., Driguez H., Planas A. Carbohydr. Res. 1998, 311:95-99.
155. Day A.G., Withers S.G. Biochem. Cell Biol. 1986, 64:914-922.
156. Fialová P., Carmona A.T., Robina I., Ettrich R., Sedmera P., Pikrylová V., Petrásková-Hušáková L., Křen V. Tetrahedron Lett. 2005, 46:8715-8718.
157. Müllegger J., Jahn M., Chen H.-M., Warren R.A.J., Withers S.G. Protein Eng. Des. Sel. 2005, 18:33-40.
158. Kobayashi S., Kiyosada T., Shoda S. Tetrahedron Lett. 1997, 38:2111-2112.
159. Shoda S., Kiyosada T., Mori H., Kobayashi S. Heterocycles 2000, 52:599-602.
160. Ochiai H., Ohmae M., Kobayashi S. Carbohydr. Res. 2004, 339:2769-2788.
161. Li B., Zeng Y., Hauser S., Song H., Wang L.-X. J. Am. Chem. Soc. 2005, 127:9692-9693.
162. Zeng Y., Wang J., Li B., Hauser S., Li H., Wang L.-X. Chem. Eur. J. 2006, 12:3355-3364.
163. Fujita M., Shoda S., Haneda K., Inazu T., Takegawa K., Yamamoto K. Biochim. Biophys. Acta 2001, 1528:9-14.
164. Kobayashi S., Morii H., Itoh R., Kimura S., Ohmae M. J. Am. Chem. Soc. 2001, 123:11825-11826.
165. Fujikawa S., Ohmae M., Kobayashi S. Biomacromol. 2005, 6:2935-2942.
166. Petit J.-M., Paquet F., Beau J.-M. Tetrahedron Lett. 1991, 32:6125-6128.
167. Zinin A.I., Eneyskaya E.V., Shabalin K.A., Kulminskaya A.A., Shishlyannikov S.M., Neustroev K.N. Carbohydr. Res. 2002, 337:635-642.
168. Meulenbeld G.H., Hartmans S. Appl. Microbiol. Biotechnol. 2001, 56:700-706.
169. Kimura T., Takayama S., Huang H., Wong C.-H. Angew. Chem., Int. Ed. Engl. 1996, 35:2348-2350.
170. MacManus D.A., Grabowska U., Biggadike K., Bird M.I., Davies S., Vulfson E.N., Gallagher T. J. Chem. Soc., Perkin Trans. 1, 1999, 295-305.
171. Hušáková L., Riva S., Casali M., Nicotra S., Kuzma M., Huňková Z., Křen V. Carbohydr. Res. 2001, 331:143-148.
172. Fialová P., Namdjou D.-J., Ettrich R., Pikrylová V., Rauvolfová J., Krenek K., Kuzma M., Elling L., Bezouška K., Křen V. Adv. Synth. Catal. 2005, 347:997-1006.
173. Krist P., Herkommerová-Rajnochová E., Rauvolfová J., Semenuk T., Vavrušková P., Pavlícek J., Bezouška K., Petruš L., Křen V. Biochem. Biophys. Res. Commun. 2001, 287:11-20.
174. Weingarten S., Thiem J. Org. Biomol. Chem. 2004, 2:961-962.
175. Murata T., Kosugi M., Nakamura T., Urashima T., Usui T. Biosci., Biotechnol., Biochem. 2001, 65:2456-2464.
176. Greve L.C., Prody G.A., Hedrick J.L. Gamete Res. 1985, 12:305-312.
177. Weignerová L., Vavrušková P., Pišvejcová A., Thiem J., Křen V. Carbohydr. Res. 2003, 338:1003-1008.
178. Nishio T., Kanai C., Hakamata W., Ogawa M., Nakajima K., Hoshino S., Matsuishi A., Kawachi R., Oku T. Biosci., Biotechnol., Biochem. 2003, 67:1024-1029.
179. Nishimura T., Momohara I., Ishikara M. Abstract Book of 10th European Carbohydrate Symposium 1999, National University of Ireland, Galway, Ireland. A. Savage, A. Moran, M. Tuohy (Eds.).
180. Withers S.G., Aebersold R. Protein Sci. 1995, 4:361-372.
181. Withers S.G., Street I.P., Bird P., Dolphin D.H. J. Am. Chem. Soc. 1987, 109:7530-7531.
182. Withers S.G., Rupitz K., Street I.P. J. Biol. Chem. 1988, 263:7929-7932.
183. Braun C., Brayer G.D., Withers S.G. J. Biol. Chem. 1995, 270:26778-26781.
184. McCarter J.D., Withers S.G. J. Am. Chem. Soc. 1996, 118:241-242.
185. Ly H.D., Howard S., Shum K., He S., Zhu A., Withers S.G. Carbohydr. Res. 2000, 329:539-547.
186. Vocadlo D.J., Mayer C., He S., Withers S.G. Biochemistry 2000, 39:117-126.
187. Molodtsov N.V., Vafina M.G. Int. J. Biochem. 1974, 5:235-237.
188. Molodtsov N.V., Vafina M.G. Int. J. Biochem. 1974, 5:239-240.
189. Molodtsov N.V., Vafina M.G. Comp. Biochem. Physiol. B 1974, 48:257-260.
190. Molodtsov N.V., Vafina M.G. Biochim. Biophys. Acta 1974, 364:296-303.
191. Molodtsov N.V., Vafina M.G. Comp. Biochem. Physiol. B: Biochem. Mol. Biol. 1975, 51:313-315.
192. Vafina M.G., Molodtsov N.V. Carbohydr. Res. 1976, 47:188-194.
193. Leaback D.H., Walker P.G. Biochem. J. 1967, 104:70P-71P.
194. Fialová P., Weignerová L., Rauvolfová J., Pikrylová V., Pišvejcová A., Ettrich R., Kuzma M., Sedmera P., Křen V. Tetrahedron 2004, 60:693-701.
195. Hashimoto H., Katayama C., Goto M., Okinaga T., Kitahata S. Biosci., Biotechnol., Biochem. 1995, 59:179-183.
196. Rauvolfová J., Kuzma M., Weignerová L., Fialová P., Pikrylová V., Pišvejcová A., Macková M., Křen V. J. Mol. Catal. B: Enzym. 2004, 29:233-239.
197. Singh S., Packwood J., Crout D.H.G. J. Chem. Soc., Chem. Commun. 1994, 2227-2228.
198. Bucke C.J. Chem. Technol. Biotechnol. 1996, 67:217-220.
199. Usui T., Kubota S., Ohi H. Carbohydr. Res. 1993, 244:315-323.
200. Yang Z., Pan W. Enzyme Microb. Technol. 2005, 37:19-28.
201. Klaffke W. Programme of 6th European Training Course on Carbohydrates 2000, Lajos Kossuth University, Debrecen, Hungary.
202. Nilsson K.G.I. Carbohydr. Res. 1990, 204:79-83.
203. Crout D.H.G., Howarth O.W., Singh S., Swoboda B.E.P., Critchley P., Gibson W.T. J. Chem. Soc., Chem. Commun. 1991, 1550-1551.
204. Nilsson K.G.I. Carbohydr. Res. 1989, 188:9-17.
205. Crout D.H.G., MacManus D.A., Ricca J.-M., Singh S., Critchley P., Gibson W.T. Pure Appl. Chem. 1992, 64:1079-1084.
206. Singh S., Scigelova M., Critchley P., Crout D.H.G. Carbohydr. Res. 1998, 305:363-370.
207. López R., Fernández-Mayoralas A. J. Org. Chem. 1994, 59:737-745.
208. Singh S., Scigelova M., Vic G., Crout D.H.G. J. Chem. Soc., Perkin Trans. 1, 1996, 1921-1926.
209. MacManus D.A., Vulfson E.N. Biotechnol. Bioeng. 2000, 69:585-590.
210. Weignerová L., Sedmera P., Huňková Z., Halada P., Křen V., Casali M., Riva S. Tetrahedron Lett. 1999, 40:9297-9299.
211. Look G.C., Wong C.-H. Tetrahedron Lett. 1992, 33:4253-4256.
212. Simerská P., Pišvejcová A., Kuzma M., Sedmera P., Křen V., Nicotra S., Riva S. J. Mol. Catal. B: Enzym. 2004, 29:219-225.
213. Kuhn R., Baer H.H., Gauhe A. Chem. Ber. 1955, 88:1713-1723.
214. Herrmann G.F., Kragl U., Wandrey C. Angew. Chem., Int. Ed. Engl. 1993, 32:1342-1343.
215. Vetere A., Paoletti S. Biochem. Biophys. Res. Commun. 1996, 219:6-13.
216. Křen V., Thiem J. Angew. Chem., Int. Ed. Engl. 1995, 34:893-895.
217. Hsuanyu Y., Laidler K.J. Can. J. Biochem. Cell Biol. 1985, 63:167-175.
218. Barnett J.E.G., Jarvis W.T.S., Munday K.A. Biochem. J. 1967, 103:699-704.
219. Breccia J.D., Morán A.C., Castro G.R., Siñeriz F. J. Chem. Technol. Biotechnol. 1998, 71:241-245.
220. Miller G.L. Anal. Chem. 1959, 31:426-428.
221. Mega T., Ikenaka T., Matsushima Y. J. Biochem. (Tokyo) 1970, 68:109-117.
222. Tarentino A.L., Maley F. Methods Enzymol. 1972, 28:772-776.
223. Shibata H., Yagi T. Clin. Chim. Acta 1996, 251:53-64.
224. Selwood T., Sinnott M.L. Biochem. J. 1988, 254:899-901.
225. Leaback D.H., Walker P.G. Biochem. J. 1961, 78:151-156.
226. Linko-Löppönen S., Mäkinen M. Anal. Biochem. 1985, 148:50-53.
227. Mayer C., Jakeman D.L., Mah M., Karjala G., Gal L., Warren R.A.J., Withers S.G. Chem. Biol. 2001, 8:437-443.
228. Sasamoto K., Ohkura Y. Chem. Pharm. Bull. 1991, 39:411-416.
229. Konstantinidis A., Sinnott M.L. Biochem. J. 1991, 279:587-593.
230. Kanie Y., Kanie O. Electrophoresis 2003, 24:1111-1118.
231. Tyl C., Felsinger S., Brecker L. J. Mol. Catal. B: Enzym. 2004, 28:55-63.
232. Dion M., Nisole A., Spangenberg P., André C., Glottin-Fleury A., Mattes R., Tellier C., Rabiller C. Glycoconjugate J. 2001, 18:215-223.
233. Blanchard J.E., Withers S.G. Chem. Biol. 2001, 8:627-633.
234. Lin H., Tao H., Cornish V.W. J. Am. Chem. Soc. 2004, 126:15051-15059.
235. Klibanov A.M., Samokhin G.P., Martinek K., Berezin I.V. Biotechnol. Bioeng. 1977, 19:1351-1361.
236. Halling P.J. Enzyme Microb. Technol. 1984, 6:513-516.
237. Zaks A., Klibanov A.M. Science 1984, 224:1249-1251.
238. Zaks A., Klibanov A.M. Proc. Natl. Acad. Sci. U.S.A. 1985, 82:3192-3196.
239. Klibanov A.M. Chem. Tech. (Leipzig) 1986, 16:354-359.
240. Halling P.J., Kvittingen L. Trends Biotechnol. 1999, 17:343-344.
241. Klibanov A.M. Trends Biotechnol. 2000, 18:85-86.
242. Kvittingen L. Trends Biotechnol. 2000, 18:86.
243. Arnold F.H. FASEB J. 1993, 7:744-749.
244. Arnold F.H. Nature 2001, 409:253-257.
245. Klibanov A.M. Nature 2001, 409:241-246.
246. Halling P.J. Curr. Opin. Chem. Biol. 2000, 4:74-80.
247. Castro G.R., Knubovets T. Crit. Rev. Biotechnol. 2003, 23:195-231.
248. Zaks A., Klibanov A.M. J. Biol. Chem. 1988, 263:8017-8021.
249. Laane C., Boeren S., Vos K., Veeger C. Biotechnol. Bioeng. 1987, 30:81-87.
250. Chin J.T., Wheeler S.L., Klibanov A.M. Biotechnol. Bioeng. 1994, 44:140-145.
251. Rariy R.V., Klibanov A.M. Proc. Natl. Acad. Sci. U.S.A. 1997, 94:13520-13523.
252. Rariy R.V., Klibanov A.M. Biotechnol. Bioeng. 1999, 62:704-710.
253. Knubovets T., Osterhout J.J., Klibanov A.M. Biotechnol. Bioeng. 1999, 63:242-248.
254. Knubovets T., Osterhout J.J., Connolly P.J., Klibanov A.M. Proc. Natl. Acad. Sci. U.S.A. 1999, 96:1262-1267.
255. Volkin D.B., Staubli A., Langer R., Klibanov A.M. Biotechnol. Bioeng. 1991, 37:843-853.
256. Klibanov A.M. Nature 1995, 374:596.
257. Zacharis E., Halling P.J., Rees D.G. Proc. Natl. Acad. Sci. U.S.A. 1999, 96:1201-1205.
258. Vic G., Biton J., Le Beller D., Michel J.-M., Thomas D. Biotechnol. Bioeng. 1995, 46:109-116.
259. Blakeney A.B., Stone B.A. FEBS Lett. 1985, 186:229-232.
260. Lineback D.R., Sayeed A.L. Carbohydr. Res. 1971, 17:453-456.
261. Griebenow K., Klibanov A.M. J. Am. Chem. Soc. 1996, 118:11695-11700.
262. Yoon J.H., Rhee J.S. Carbohydr. Res. 2000, 327:377-383.
263. Vic G., Thomas D. Tetrahedron Lett. 1992, 33:4567-4570.
264. Finch P., Yoon J.H. Carbohydr. Res. 1997, 303:339-345.
265. Magnuson D.K., Bodley J.W., Evans D.F. J. Solution Chem. 1984, 13:583-587.
266. van Rantwijk F., Lau R.M., Sheldon R.A. Trends Biotechnol. 2003, 21:131-138.
267. Husum T.L., Jørgensen C.T., Christensen M.W., Kirk O. Biocatal. Biotrans. 2001, 19:331-338.
268. Kaftzik N., Wasserscheid P., Kragl U. Org. Proc. Res. Dev. 2002, 6:553-557.
269. Kaftzik N., Neumann S., Kula M.-R., Kragl U. Enzymatic condensation reactions in ionic liquids. Ionic Liquids as Green Solvents: Progress and Prospects 2003, 206-211. American Chemical Society, Washington, DC, ACS Symposium Series 856. R.D. Rogers, K.R. Seddon (Eds.).
270. Summers C.A., Flowers R.A. Protein Sci. 2000, 9:2001-2008.
271. Kragl U., Eckstein M., Kaftzik N. Curr. Opin. Biotechnol. 2002, 13:565-571.
272. Millqvist-Fureby A., Gill I.S., Vulfson E.N. Biotechnol. Bioeng. 1998, 60:190-196.
273. Millqvist-Fureby A., MacManus D.A., Davies S., Vulfson E.N. Biotechnol. Bioeng. 1998, 60:197-203.
274. Gill I., Valivety R. Angew. Chem., Int. Ed. Engl. 2000, 39:3801-3804.
275. Ogino H., Ishikawa H. J. Biosci. Bioeng. 2001, 91:109-116.
276. Krishna S.H. Biotechnol. Adv. 2002, 20:239-267.
277. Mori T., Okahata Y. Tetrahedron Lett. 1997, 38:1971-1974.
278. Okahata Y., Fujimoto Y., Ijiro K. J. Org. Chem. 1995, 60:2244-2250.
279. Mori T., Fujita S., Okahata Y. Carbohydr. Res. 1997, 298:65-73.
280. Okahata Y., Mori T. J. Mol. Catal. B: Enzym. 1998, 5:119-123.
281. Mori T., Okahata Y. J. Chem. Soc., Chem. Commun. 1998, 2215-2216.
282. Grandi C., Smith R.E., Luisi P.L. J. Biol. Chem. 1981, 256:837-843.
283. Vulfson E.N., Patel R., Beecher J.E., Andrews A.T., Law B.A. Enzyme Microb. Technol. 1990, 12:950-954.
284. Otto R.T., Bornscheuer U.T., Syldatk C., Schmid R.D. Biotechnol. Lett. 1998, 20:437-440.
285. Germain P., Makaren J.S., Crichton R.R. Biotechnol. Bioeng. 1988, 32:249-254.
286. Tyagi R., Batra R., Gupta M.N. Enzyme Microb. Technol. 1999, 24:348-354.
287. Barbaric S., Leuštek I., Pavlovic B., Cesi V., Mildner P. Ann. N.Y. Acad. Sci. 1988, 542:173-179.
288. Binkley W.W. Adv. Carbohyd. Chem. Biochem. 1955, 10:55-94.
289. Sakai K., Katsumi R., Ohi H., Usui T., Ishido Y. J. Carbohydr. Chem. 1992, 11:553-565.
290. Petrásková L., Charvátová A., Pikrylová V., Kristová V., Rauvolfová J., Martínková L., Jiménez-Barbero J., Aboitiz N., Petruš L., Křen V. J. Chromatogr., A 2006, 1127:126-136.
291. Herrmann G.F., Ichikawa Y., Wandrey C., Gaeta F.C.A., Paulson J.C., Wong C.-H. Tetrahedron Lett. 1993, 34:3091-3094.
292. Vetere A., Paoletti S. FEBS Lett. 1996, 399:203-206.
293. Suzuki K., Matsuo I., Isomura M., Ajisaka K. J. Carbohydr. Chem. 2002, 21:99-111.
294. Ito Y., Paulson J.C. J. Am. Chem. Soc. 1993, 115:7862-7863.
295. Hokke C.H., van der Eijnden D.H. Carbohydr. Res. 1997, 305:463-468.
296. Cheetham P.S.J. The applications of enzymes in industry. Handbook of Enzyme Biotechnology 1995, 420-552. London, Ellis. A. Wiseman (Ed.).
297. Iamane T. Sucr. Belge/Sugar Ind. Abstr. 1971, 90:345-348.
298. Soares N.F.F., Hotchkiss J.H. J. Food Sci. 1998, 63:61-65.
299. Puri M., Banerjee U.C. Biotechnol. Adv. 2000, 18:207-217.
300. Spagna G., Barbagallo R.N., Martino A., Pifferi P.G. Enzyme Microb. Technol. 2000, 27:522-530.
301. Gueguen Y., Chemardin P., Pien S., Arnaud A., Galzy P. J. Biotechnol. 1997, 55:151-156.
302. Cheetham, P. S. J.; Quail, M. A. Process for Preparing L-Rhamnose; US Patent 5,077,206, December 31, 1991.
303. de Roode B.M., Franssen M.C.R., van der Padt A., Boom R.M. Biotechnol. Prog. 2003, 19:1391-1402.
304. Johansson, I.; Dahlgren, L. Alkyl glycoside and use thereof; US Patent 5,681,949, October 28, 1997.
305. von Rybinski W. Curr. Opin. Colloid Interface Sci. 1996, 1:587-597.
306. Luther, H.; Stehlin, A.; Minklei, M. Sunscreen compositions; US Patent 5,980,872, November 9, 1999.
307. Křen V., Martínková L. Curr. Med. Chem. 2001, 8:1303-1328.
308. de Roode B.M., van Beek J., van der Padt A., Franssen M.C.R., Boom R.M. Enzyme Microb. Technol. 2001, 29:513-520.
309. Tsitsimpikou C., Xhirogianni K., Markopoulou O., Kolisis F.N. Biotechnol. Lett. 1996, 18:387-392.
310. Baur, R.; Houben, J.; Jaeger, H.-U.; Oftring, A.; Perner, J. Purification of long-chain alkylglucosides; US Patent 4,939,246, July 3, 1990.
311. Schmid, K. H.; Biermann, M. Process for the purification of alkyl glycosides, products obtainable by this process and their use; US Patent4,889,925, December 26, 1989.
312. Nakakuki T. Trends Glycosci. Glycotechnol. 2003, 15:57-64.
313. Kometani T., Nishimura T., Nakae T., Takii H., Okada S. Biosci., Biotechnol., Biochem. 1996, 60:645-649.
314. Suzuki Y., Suzuki K. Agric. Biol. Chem. 1991, 55:181-187.
315. Prenosil J.E., Stuker E., Bourne J.R. Biotechnol. Bioeng. 1987, 30:1026-1031.
316. Yun J.W. Enzyme Microb. Technol. 1996, 19:107-117.
317. Sangeetha P.T., Ramesh M.N., Prapulla S.G. Trends Food Sci. Technol. 2005, 16:442-457.
318. Hirayama M., Sumi N., Hidaka H. Agric. Biol. Chem. 1989, 53:667-673.
319. Yun J.W., Jung K.H., Oh J.W., Lee J.H. Appl. Biochem. Biotechnol. 1990, 24-25:299-308.
320. Dickerson A.G. Biochem. J. 1972, 129:263-272.
321. Kumano Y., Sakamoto T., Egawa M., Iwai I., Tanaka M., Yamamoto I. J. Nutr. Sci. Vitaminol. 1998, 44:345-359.
322. Aga H., Yoneyama M., Sakai S., Yamamoto I. Agri. Biol. Chem. 1991, 55:1751-1756.
323. Wahler D., Reymond J.-L. Curr. Opin. Chem. Biol. 2001, 5:152-158.
324. Pascal M., Kunst F., Lepesant J.-A., Dedonder R. Biochimie 1971, 53:1059-1066.
325. Schenkman S., Jiang M.-S., Hart G.W., Nussenzweig V. Cell 1991, 65:1117-1125.
326. Albenne C., Skov L.K., Mirza O., Gajhede M., Feller G., D'Amico S., André G., Potocki-Véronèse G., van der Veen B., Monsan P., Remaud-Simeon H. J. Biol. Chem. 2004, 279:726-734.
327. Street A.G., Mayo S.L. Structure 1999, 7:R105-R109.
328. Mackenzie L.F., Wang Q., Warren R.A.J., Withers S.G. J. Am. Chem. Soc. 1998, 120:5583-5584.
329. Wang Q.P., Graham R.W., Trimbur D., Warren R.A.J., Withers S.G. J. Am. Chem. Soc. 1994, 116:11594-11595.
330. Mayer C., Zechel D.L., Reid S.P., Warren R.A.J., Withers S.G. FEBS Lett. 2000, 466:40-44.
331. Jakeman D.L., Withers S.G. Trends Glycosci. Glycotechnol. 2002, 14:13-25.
332. Trincone A., Perugino G., Rossi M., Moracci M. Bioorg. Med. Chem. Lett. 2000, 10:365-368.
333. Moracci M., Trincone A., Perugino G., Ciaramella M., Rossi M. Biochemistry 1998, 37:17262-17270.
334. Perugino G., Trincone A., Rossi M., Moracci M. Trends Biotechnol. 2004, 22:31-37.
335. Malet C., Planas A. FEBS Lett. 1998, 440:208-212.
336. Fort S., Boyer V., Greffe L., Davies G.J., Moroz O., Christiansen L., Schülein M., Cottaz S., Driguez H. J. Am. Chem. Soc. 2000, 122:5429-5437.
337. Okuyama M., Mori H., Watanabe K., Kimura A., Chiba S. Biosci., Biotechnol., Biochem. 2002, 66:928-933.
338. Tolborg J.F., Petersen L., Jensen K.J., Mayer C., Jakeman D.J., Warren R.A.J., Withers S.G. J. Org. Chem. 2002, 67:4143-4149.
339. Matsui I., Ishikawa K., Miyairi S., Fukui S., Honda K. Biochim. Biophys. Acta 1991, 1077:416-419.
340. Rivera M.H., López-Munguía A., Soberón X., Saab-Rincón G. Protein Eng. 2003, 16:505-514.
341. Hansson T., Kaper T., van der Oost J., de Vos W.M., Adlercreutz P. Biotechnol. Bioeng. 2001, 73:203-210.
342. Jahn M., Chen H.M., Müllegger J., Marles J., Warren R.A.J., Withers S.G. J. Chem. Soc., Chem. Commun. 2004, 274-275.
343. Jahn M., Withers S.G. Biocatal. Biotrans. 2003, 21:159-166.
344. Fierobe H.-P., Mirgorodskaya E., McGuire K.A., Roepstorff P., Svensson B., Clarke A.J. Biochemistry 1998, 37:3743-3752.
345. Tao H., Cornish V.W. Curr. Opin. Chem. Biol. 2002, 6:858-864.
346. Jaeger K.-E., Eggert T., Eipper A., Reetz M.T. Appl. Microbiol. Biotechnol. 2001, 55:519-530.
347. Arnold F.H., Wintrode P.L., Miyazaki K., Gershenson A. Trends Biochem. Sci. 2001, 26:100-106.
348. Wahler D., Reymond J.-L. Curr. Opin. Biotechnol. 2001, 12:535-544.
349. Reetz M.T. Angew. Chem., Int. Ed. Engl. 2002, 41:1335-1338.
350. Stemmer W.P.C. Proc. Natl. Acad. Sci. U.S.A. 1994, 91:10747-10751.
351. Zhao H., Giver L., Shao Z., Affholter J.A., Arnold F.H. Nat. Biotechnol. 1998, 16:258-261.
352. Caldwell R.C., Joyce G.F. PCR Methods Appl. 1992, 2:28-33.
353. Flores H., Ellington A.D. J. Mol. Biol. 2002, 315:325-337.
354. Murashima K., Kosugi A., Doi R.H. Mol. Microbiol. 2002, 45:617-626.
355. Feng H.-Y., Drone J., Hoffmann L., Tran V., Tellier C., Rabiller C., Dion M. J. Biol. Chem. 2005, 280:37088-37097.
356. Dion M., Osanjo G., André C., Spangenberg P., Rabiller C., Tellier C. Glycoconjugate J. 2001, 18:457-464.
357. Stefan A., Radeghieri A., Vara Y., Rodriguez A.G., Hochkoeppler A. FEBS Lett. 2001, 493:139-143.