Synthesis of stereochemical probes for new fluorogenic assays for yeast transketolase variants

Tetrahedron

Volumn 62, Issue 17, 2006, Pages 3969-3976

  Sevestre, Aurélie ^a   Charmantray, Franck ^a   Hélaine, Virgil ^a   Lásiková, Angelika ^a   Hecquet, Laurence ^a  

^a CNRS   (France)

Author keywords

C C bond formation; Enzyme evolution; Fluorogenic assays; High throughput screening; Transketolase

Indexed keywords

ENZYME VARIANT; FUNGAL ENZYME; KETOSE; MUTANT PROTEIN; RIBOSE; TARTARIC ACID; TRANSKETOLASE;

ARTICLE; ENZYME ACTIVITY; ENZYME ASSAY; ENZYME SUBSTRATE; MOLECULAR PROBE; MUTAGENESIS; PRIORITY JOURNAL; REPRODUCIBILITY; SCREENING; SENSITIVITY AND SPECIFICITY; STEREOCHEMISTRY; SYNTHESIS; WILD TYPE;

EID: 33646016249     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.02.033     Document Type: Article

References (52)

1. Jaeger K.E., and Reetz M.T. Curr. Opin. Chem. Biol. 4 (2000) 68-73
2. Beisson F., Tiss A., Riviere C., and Verger R. Eur. J. Lipid Sci. Technol. (2000) 133-153
3. MacBeath G., and Hilvert D. J. Am. Chem. Soc. 116 (1994) 6101-6106
4. Tawfik D.S., Green B.S., Chap R., Sela M., and Eshhar Z. Proc. Natl. Acad. Sci. USA 90 (1993) 373-377
5. Taylor S.J., and Morken J.P. Science 280 (1998) 267-270
6. Holzwarth A., Schmidt H.W., and Maier W.F. Angew. Chem., Int. Ed. 37 (1998) 2644-2647
7. Reetz M.T., Becker M.H., Klein H.W., and Stockigt D. Angew. Chem., Int. Ed. 38 (1999) 1758-1761
8. Reetz M.T. Angew. Chem., Int. Ed. 40 (2001) 284-310
9. Goddard J.P., and Reymond J.L. Trends Biotechnol. 22 (2004) 363-370
10. Klein G., and Reymond J.L. Bioorg. Med. Chem. Lett. 8 (1998) 1113-1116
11. Klein G., and Reymond J.L. Helv. Chim. Acta 82 (1999) 400-407
12. Badalassi F., Wahler D., Klein G., Crotti P., and Reymond J.L. Angew. Chem., Int. Ed. 39 (2000) 4067-4070
13. Wahler D., Badalassi F., Crotti P., and Reymond J.L. Angew.Chem., Int. Ed. 40 (2001) 4457-4460
14. Wahler D., Badalassi F., Crotti P., and Reymond J.L. Chem. Eur. J. 8 (2002) 3211-3228
15. Perez-Carlon R., Jourdain N., and Reymond J.L. Chem. Eur. J. 6 (2000) 4154-4162
16. Gonzalez-Garcia E., Hélaine V., Klein G., Schuermann M., Sprenger G.A., Fessner W.D., and Reymond J.L. Chem. Eur. J. 9 (2003) 893-899
17. Bolte J., Demuynck C., Hecquet L., and Samaki H. Carbohydr. Res. 206 (1990) 79-85
18. Ziegler T., Straub A., and Effenberger F. Angew. Chem., Int. Ed. Engl. 27 (1988) 716-721
19. Kobori Y., Myles D.C., and Withesides G.M. J. Org. Chem. 22 (1991) 5899-5907
20. Morris K.G., Smith M.E.B., and Turner N.J. Tetrahedron: Asymmetry 7 (1996) 2185-2188
21. Zimmermann F.T., Schneider A., Schörken Y., Sprenger G.A., and Fessner W.D. Tetrahedron: Asymmetry 10 (1999) 1643-1646
22. Wikner C., Meshalkina L., Nilsson U., Nikkola M., Lindqvist Y., and Schneider G. J. Biol. Chem. 269 (1994) 32144-32150
23. Nilsson U., Hecquet L., Gefflaut T., Guérard C., and Schneider G. FEBS Lett. 424 (1998) 49-52
24. André C., Guérard C., Hecquet L., Demuynck C., and Bolte J. J. Mol. Catal. B: Enzym. 5 (1998) 459-466
25. Guérard C., Alphand V., Archelas A., Demuynck C., Hecquet L., Furstoss R., and Bolte J. Eur. J. Org. Chem. 1 (1999) 3399-3402
26. Crestia D., Guérard C., Veschambre H., Hecquet L., Demuynck C., and Bolte J. Tetrahedron: Asymmetry 12 (2001) 869-876
27. Sevestre A., Hélaine V., Guyot G., Martin C., and Hecquet L. Tetrahedron Lett. 44 (2003) 827-830
28. Clarke D.J., and Robinson R.S. Tetrahedron 58 (2002) 2831-2838
29. Smith A.B., and Jerris P.J. Tetrahedron Lett. 21 (1980) 711-714
30. Machajewski T.D., and Wong C.H. Angew. Chem., Int. Ed. 39 (2000) 1352-1375
31. Kobori Y., Myles D.C., and Whitesides G.M. J. Org. Chem. 57 (1992) 5899-5907
32. Wymer N., and Toone E.J. Curr. Opin. Chem. Biol. 4 (2000) 110-119
33. Wong C.H., and Whitesides G.M. J. Org. Chem. 48 (1983) 3199-3205
34. Effenberger F., and Null V. Liebigs Ann. Chem. (1992) 1211-1212
35. Ziegler T., Straub A., and Effenberger F. Angew. Chem., Int. Ed. Engl. 27 (1988) 716-717
36. Bolte J., Demuynck C., and Samaki H. Tetrahedron Lett. 28 (1987) 5525-5528
37. Charmantray F., El Blidi L., Gefflaut T., Hecquet L., Bolte J., and Lemaire M. J. Org. Chem. 69 (2004) 9310-9312
38. Musich J.A., and Rapoport H. J. Am. Chem. Soc. 100 (1978) 4865-4872
39. Batsanov A.S., Begley M.J., Fletcher J.A., and Murphy J.A. J. Chem. Soc., Perkin Trans. 1 (1995) 1281-1294
40. Valverde S., Herradon B., Rabanal R.M., and Martin-Lomas M. Can. J. Chem. 65 (1987) 332
41. Baumberger F., Vasella A., and Schauer R. Helv. Chim. Acta 69 (1986) 1927-1935
42. Friestad K.G., and Massari E.S. J. Org. Chem. 69 (2004) 863-875
43. Kaskar B., Haise G.L., Michalak R.S., and Vishnuvajjala B.R. Synthesis 11 (1990) 1031-1032
44. Sivets G.G., Klennitskaya T.V., Zhernosek E.V., and Mikhailopulo I.A. Synthesis 2 (2002) 253-259
45. Clauss R., and Hunter R. J. Chem. Soc., Perkin Trans. 1 (1997) 71-76
46. Kane P.D., and Mann J. J. Chem. Soc., Perkin Trans. 1 (1984) 657-660
47. Kim D.K., Kim G., and Kim Y.W. J. Chem. Soc., Perkin Trans. 1 8 (1996) 803-808
48. Valverde S., Herradon B., Rabanal R.M., and Martin-Lomas M. Can. J. Chem. 65 (1987) 332
49. Paterson I., Norcross R.D., Ward R.A., Romea P., and Lister M.A. J. Am. Chem. Soc. 116 (1994) 11287-11314
50. Taylor S.L., Lee D.Y., and Martin J.C. J. Org. Chem. 48 (1983) 4156-4158
51. Szarek W.A., Zamojski A., Tiwari K.N., and Ison E.R. Tetrahedron Lett. 27 (1986) 3827-3830
52. Hecquet L., Demuynck C., and Bolte J. J. Mol. Catal. B: Enzym. 6 (2001) 797-802