Regioselective monohydrolysis of per-O-acetylated-1-substituted-β-glucopyranosides catalyzed by immobilized lipases

Tetrahedron

Volumn 64, Issue 47, 2008, Pages 10721-10727

  Mendes, Adriano A ^a   Rodrigues, Dasciana S ^a   Filice, Marco ^a   Fernandez Lafuente, Roberto ^a   Guisan, Jose M ^a   Palomo, Jose M ^a  

^a CSIC   (Spain)

Author keywords

Glucopyranosides; Immobilization; Lipase; Monohydrolysis; Regioselectivity

Indexed keywords

1 (4 NITROPHENYL) 2,3,4 TRI O ACETYL BETA DEXTRO XYLOPYRANOSIDE; 2 ACETAMIDO 2 DEOXY 1 (4 NITROPHENYL) 3,4,6 TRI O ACETYL BETA DEXTRO GLUCOPYRANOSIDE; CARBOHYDRATE DERIVATIVE; GLUCOPYRANOSIDE; IMMOBILIZED ENZYME; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; ARTICLE; ASPERGILLUS NIGER; CANDIDA ANTARCTICA; CANDIDA RUGOSA; COVALENT BOND; ENZYME IMMOBILIZATION; HYDROLYSIS; HYDROPHOBICITY; ION EXCHANGE; NONHUMAN; PRIORITY JOURNAL;

ASPERGILLUS NIGER; CANDIDA; CANDIDA ANTARCTICA;

EID: 53149114800     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.08.099     Document Type: Article

References (52)

1. Varki A. Glycobiology 3 (1993) 97
2. Ryan C.A. Proc.Natl. Acad. Sci. U.S.A 91 (1994) 1
3. Bertozzi C.R., and Kiessling L.L. Science 291 (2001) 2357
4. Giannis A. Angew. Chem., Int. Ed. Engl. 33 (1994) 178
5. Blanchard S., and Thorson J.S. Curr. Opin. Chem. Biol. 10 (2006) 263
6. Borges de Melo E., da Silveira Gomes A., and Carvalho I. Tetrahedron 62 (2006) 10277
7. von Rybinski W., and Karlheinz H. Angew. Chem., Int. Ed. 37 (1998) 1328
8. Wegner M., and von Rybinski W. Tenside Surfact. Deterg. 38 (2001) 24
9. Rosevear P., Vanaken T., Baxter J., and Ferguson-Miller S. Biochemistry 19 (1980) 4108
10. Rigaud J.L., Chami M., Lambert O., Levy D., and Ranck J.L. Biochem. Biophys. Acta 1508 (2000) 112
11. Uchegbu I.F., and Vyas S.P. Int. J. Pharm. 172 (1998) 33
12. Liener I.E., Sharon N., and Goldstein I.J. The Lectins: Properties, Functions, and Applications in Biology and Medicine (1986), Academic, Orlando, FL
13. Toshima K., and Tatsuta K. Chem. Rev. 93 (1993) 1503
14. Payne R.J., Ficht S., Tang S., Brik A., Yang Y.-Y., Case D.A., and Wong C.-H. J. Am. Chem. Soc. 129 (2007) 13527
15. Katritzky A.R., Narindoshvili T., Draghici B., and Angrish P. J. Org. Chem. 73 (2008) 511
16. Nikolakakis A., Haidara K., Sauriol F., Mamer O., and Zamir L.O. Bioorg. Med. Chem. 11 (2003) 1551
17. Campo V.L., Carvalho I., Allman S., Davis B.G., and Field R.A. Org. Biomol. Chem. 5 (2007) 2645
18. Palomo J.M., Lumbierres M., and Waldmann H. Angew. Chem., Int. Ed. 45 (2006) 477
19. Gibson M.I., Hunt G.J., and Cameron N.R. Org. Biomol. Chem. 5 (2007) 2756
20. Disney D., and Seeberger P.H. Chem. Biol. 11 (2004) 1701
21. Seeberger P.H. Chem. Soc. Rev. 37 (2008) 19
22. Ghanem A., and Aboul-Enein H.Y. Chirality 17 (2005) 44
23. Wong C.-H., and Whitesides G.M. Enzymes in Synthetic Organic Chemistry (1994), Pergamon, Oxford
24. Hennen W.J., Sweers H.M., Wang Y.F., and Wong C.-H. J. Org. Chem. 53 (1988) 4939
25. Shaw J.F., and Klibanov A.M. Biotechnol. Bioeng. 29 (1987) 648
26. Mateo C., Grazu V., Palomo J.M., Lopez-Gallego F., Fernandez-Lafuente R., and Guisán J.M. Nat. Protoc. 2 (2007) 1022
27. Bornscheuer U.T. Curr. Opin. Biotechnol. 13 (2002) 543
28. Turner N.J. Curr. Opin. Biotechnol. 14 (2003) 401
29. Larissegger-Schnell B., Glueck S.M., Kroutil W., and Faber K. Tetrahedron 62 (2006) 2912
30. Brady L., Brzozowski A.M., Derewenda Z.S., Dodson E., Dodson G., Tolley S., Turkenburg J.P., Christiansen L., Huge-Jensen B., Norskov L., Thim L., and Menge U. Nature 43 (1990) 767
31. Aloulou A., Rodriguez J.A., Fernandez S., van Oosterhout D., Puccinelli D., and Carrière F. Biochim. Biophys. Acta 1761 (2006) 995
32. Mateo C., Palomo J.M., Fernández-Lorente G., Fernandez-Lafuente R., and Guisán J.M. Enzyme Microb. Technol. 40 (2007) 1451
33. Busto E., Gotor-Fernandez V., Montejo-Bernardo J., Garcia-Granda S., and Gotor V. Org. Lett. 9 (2007) 4203
34. Palomo J.M., Segura R.L., Mateo C., Terreni M., Guisán J.M., and Fernández-Lafuente R. Tetrahedron: Asymmetry 16 (2005) 869
35. Chenevert R., Courchesne G., and Pelchat N. Bioorg. Med. Chem. 14 (2006) 5389
36. Palomo J.M., Fernández-Lorente G., Mateo C., Fuentes M., Guisán J.M., and Fernández-Lafuente R. Tetrahedron: Asymmetry 13 (2002) 2653
37. Kohler J., and Wunsch B. Tetrahedron: Asymmetry 17 (2006) 3091
38. Cabrera Z., Palomo J.M., Fernández-Lorente G., Guisán J.M., and Fernández-Lafuente R. Enzyme Microb. Technol. 40 (2007) 1280
39. Palomo J.M., Filice M., Fernandez-Lafuente R., Terreni M., and Guisan J.M. Adv. Synth. Catal. 349 (2007) 1969
40. Fernández-Lorente G., Palomo J.M., Cocca J., Mateo C., Fernández-Lafuente R., Moro P., Terreni M., and Guisán J.M. Tetrahedron 59 (2003) 5705
41. Terreni M., Salvatti R., Linati L., Fernandez-Lafuente R., Fernandez-Lorente G., Bastida A., and Guisan J.M. Carbohydr. Res. 337 (2002) 1615
42. Bastida A., Sabuquillo P., Armisen P., Fernández-Lafuente R., Huguet J., and Guisan J.M. Biotechnol. Bioeng. 58 (1998) 486
43. Mateo C., Abian O., Bernedo M., Cuenca E., Fuentes M., Fernández-Lorente G., Palomo J.M., Grazu V., Pessela B.C.C., Giacomini C., Irazoqui G., Villarino A., Ovsejevi K., Batista-Viera F., Fernández-Lafuente R., and Guisán J.M. Enzyme Microb. Technol. 37 (2005) 456
44. Mateo C., Abian O., Fernández-Lafuente R., and Guisán J.M. Biotechnol. Bioeng. 68 (2000) 98
45. Bradford M.M. Anal. Biochem. 72 (1976) 248
46. Fernández-Lorente G., Ortiz C., Segura R.L., Fernández-Lafuente R., Guisán J.M., and Palomo J.M. Biotechnol. Bioeng. 92 (2005) 773
47. Palomo J.M., Fuentes M., Fernández-Lorente G., Mateo C., Guisan J.M., and Fernández-Lafuente R. Biomacromolecules 4 (2003) 1
48. Horrobin T., Tran Ch.H., and Crout D. J. Chem. Soc., Perkin Trans. 1 (1998) 1069
49. Temeriusz A., Gubica T., Rogowska P., Paradowska K., and Cyranski M.K. Carbohydr. Res. 340 (2005) 1175
50. Mastihubov M., and Biely P. Carbohydr. Res. 339 (2004) 1353
51. Holla E.W. Angew. Chem., Int. Ed. Engl. 28 (1989) 220
52. Filice M., Palomo J.M., Bonomi P., Bavaro T., Fernandez-Lafuente R., Guisan J.M., and Terreni M. Tetrahedron 64 (2008) 9286