Two-step enzymatic modification of solid-supported bergenin in aqueous and organic media

Tetrahedron Letters

Volumn 51, Issue 8, 2010, Pages 1220-1225

  Akbar, Umar ^a   Shin, Dong Sik ^a   Schneider, Elizabeth ^a,b   Dordick, Jonathan S ^c   Clark, Douglas S ^a  

^a University of California   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

^c RENSSELAER POLYTECHNIC INSTITUTE   (United States)

Author keywords

Biocatalysis; Enzyme cleavage; Non aqueous; Solid Phase

Indexed keywords

7 BROMO 4 BUTYRYLBERGENIN; BERGENIN; BUTYRIC ACID DERIVATIVE; CARBOXYLIC ACID; CHLORIDE PEROXIDASE; DIISOPROPYL ETHER; GLASS; LIPASE B; ORGANIC MATTER; ORGANIC SOLVENT; SUBTILISIN; UNCLASSIFIED DRUG; VINYL BUTYRATE;

AQUEOUS SOLUTION; ARTICLE; BROMINATION; CATALYSIS; CHEMICAL STRUCTURE; CONTROLLED STUDY; ENZYME DEGRADATION; ENZYME MODIFICATION; IMMOBILIZATION; SOLID; TRANSESTERIFICATION;

EID: 74049153376     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.12.119     Document Type: Article

References (48)

1. Nomura C.T., and Taguchi S. Appl. Microbiol. Biotechnol. 73 (2007) 969-979
2. Nomura C.T., Tanaka T., Gan Z., Kuwabara K., Abe H., Takase K., Taguchi K., and Doi Y. Biomacromolecules 5 (2004) 1457-1464
3. Barbetta A., Massimi M., Devirgilis L., and Dentini M. Biomacromolecules 7 (2006) 3059-3068
4. Thordarson P., Le Droumaguet B., and Velonia K. Appl. Microbiol. Biotechnol. 73 (2006) 243-254
5. Qi Q., Jones C.W., and Schlork F.J. Biomacromolecules 7 (2006) 2927-2930
6. Altreuter D.H., and Clark D.S. Curr. Opin. Biotechnol. 10 (1999) 130-136
7. Khmelnitsky Y.L., Budde C., Arnold J.M., Usyatinsky A., Clark D.S., and Dordick J.S. J. Am. Chem. Soc. 119 (1997) 11554-11555
8. Kristenansky J.L., and Khmelnitsky Y.L. Bioorg. Med. Chem. 7 (1999) 2157-2162
9. Reents R., Duraiswamy A.J., and Waldmann H. Drug Discovery Today 7 (2002) 71-76
10. Doezé R.H.P., Maltman B.A., Egan C.L., Ulijn R.V., and Flitsch S.L. Angew. Chem., Int. Ed. 43 (2004) 3138-3141
11. Humphrey C.E., Turner N.J., Easson M.A.M., Flitsch S.L., and Ulijn R.V. J. Am. Chem. Soc. 125 (2003) 13952-13953
12. Schuster M., Wang P., Paulson J.C., and Wong C.H. J. Am. Chem. Soc. 116 (1994) 1135-1136
13. Tolborg J.F., Peterson L., Jensen K.J., Mayer C., Jakeman D.L., Warren R.A.J., and Withers S.G. J. Org. Chem. 67 (2002) 4143-4149
14. Ulijn R.V., Baragaña B., Halling P.J., and Flitsch S.L. J. Am. Chem. Soc. 124 (2002) 10988-10989
15. Altreuter D.H., Dordick J.S., and Clark D.S. Biotechnol. Bioeng. 81 (2003) 809-817
16. Leon S., Quarrell R., and Lowe G. Bioorg. Med. Chem. Lett. 8 (1998) 2997-3002
17. Meldal M. Biopolymers 66 (2002) 93-100
18. Renil M., Ferraras M., Delaisse J.M., Foged N.T., and Meldal M. J. Pept. Sci. 4 (1998) 195-210
19. Salisbury C.M., Maly D.J., and Ellman J.A. J. Am. Chem. Soc. 124 (2002) 14868-14870
20. Smith H.K., and Bradley M.J. J. Comb. Chem. 1 (1999) 326-332
21. Zhu Q., Uttamchandani M., Li D.B., Lesaicherre M.L., and Yao S.Q. Org. Lett. 5 (2003) 1257-1260
22. Bohm G., Dowden J., Rice D.C., Burgess I., Pilard J., Guilbert B., Haxton A., Hunter R.C., Turner N.J., and Flitsch S.L. Tetrahedron Lett. 39 (1998) 3819-3822
23. Grether U., and Waldmann H. Chemistry 7 (2001) 959-971
24. Kress J., Zanaletti R., Amour A., Ladlow M., Frey J.G., and Bradley M. Chem. Eur. J. 8 (2002) 3769-3772
25. Maltman B.A., Bejugam M., and Flitsch S.L. Org. Biomol. Chem. 3 (2005) 2505-2507
26. Bosma A.Y., Ulijn R.V., McConnell G., Girkin J., Halling P.J., and Flitsch S.L. Chem. Commun. 21 (2003) 2790-2791
27. Gutierrez O.A., Chavez M., and Lissi E. Anal. Chem. 76 (2004) 2664-2668
28. Nishino H., Nihira T., Mori T., and Okahata Y. J. Am. Chem. Soc. 126 (2004) 2264-2265
29. Halling P.J., Ulijn R.V., and Flitsch S.L. Curr. Opin. Biotechnol. 16 (2005) 385-392
30. Brooks S.J., Coulombel L., Clark D.S., and Dordick J.S. Adv. Synth. Catal. 350 (2008) 1517-1525
31. Akbar U., Aschenbrenner C.D., Harper M.R., Johnson H.R., Dordick J.S., and Clark D.S. Biotechnol. Bioeng. 96 (2007) 1030-1039
32. Zaks A., and Klibanov A.M. Proc. Natl. Acad. Sci. U.S.A. 82 (1985) 3192-3196
33. Wescott C.A., and Klibanov A.M. J. Am. Chem. Soc. 115 (1993) 1629-1631
34. Li X., Wu Q., Lv D.S., and Lin X.F. Bioorg. Med. Chem. 14 (2006) 3377-3382
35. Mozhaev V.V., Budde C.L., Rich J.O., Usyatinsky A.Y., Michels P.C., Khmelnitsky Y.L., Clark D.S., and Dordick J.S. Tetrahedron 54 (1998) 3971-3982
36. Inada Y., Nishimura H., Takahashi K., Yoshimoto T., Saha A.R., and Saito Y. Biochem. Biophys. Res. Commun. 122 (1984) 845-850
37. Okahata Y., and Ijiro K. J. Chem. Soc., Chem. Commun. (1988) 1392-1394
38. Okazaki S.Y., Kamiya N., Abe K., Goto M., and Nakashio F. Biotechnol. Bioeng. 55 (1997) 455-460
39. Luisi P.L., Giomini M., Pileni M., and Robinson B. Biochim. Biophys. Acta 947 (1988) 209-246
40. Paradkar V.M., and Dordick J.S. Biotechnol. Bioeng. 43 (1994) 529-540
41. Schuster M., Wang P., Paulson J.C., and Wong C.H. J. Am. Chem. Soc. 116 (1994) 1135-1136
42. Heckel A., and Seebach D. Chem. Eur. J. 8 (2002) 559-572
43. Advanced ChemTech. Advanced ChemTech Handbook of Combinatorial, Organic, and Peptide Chemistry; Advanced ChemTech: Louisville, KY, 2002.
44. Vazquez J., Qushair G., and Albericio F. Methods Enzymol. 369 (2003) 21-35
45. Gaggini F., Porcheddu A., Reginato G., Rodriquez M., and Taddei M. J. Comb. Chem. 6 (2004) 805-810
46. Cournoyer J.J., Kshirsagar T., Fantauzzi P.P., Figliozzi G.M., Makdessian T., and Yan B. J. Comb. Chem. 4 (2002) 120-124
47. Attardi M.E., Porcu G., and Taddei M. Tetrahedron Lett. 41 (2000) 7391-7394
48. Vojkovsky T. Pept. Res. 8 (1995) 236-237