DNA-based hydrolytic kinetic resolution of epoxides

Tetrahedron Asymmetry

Volumn 19, Issue 20, 2008, Pages 2374-2377

  Dijk, Ewold W ^a   Feringa, Ben L ^a   Roelfes, Gerard ^a  

^a UNIVERSITY OF GRONINGEN   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

2 PYRIDYLOXIRANE DERIVATIVE; DNA; EPOXIDE; ETHYLENE OXIDE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; DNA TRANSFER; HYDROLYSIS KINETICS; PRIORITY JOURNAL; SYNTHESIS;

EID: 56949101335     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2008.10.004     Document Type: Article

References (41)

1. In: Grieco P.A. (Ed). Organic Synthesis in Water. 1st ed. (1998), Blackie, London
2. In: Lindström U.M. (Ed). Organic Reactions in Water: Principles, Strategies and Applications. 1st ed. (2007), Blackwell, Oxford
3. Reviews:. Pan C., and Wang Z. Coord. Chem. Rev. 252 (2008) 736-750
4. Lindström U.M. Chem. Rev. 102 (2002) 2751-2772
5. Kobayashi S., and Manabe K. Acc. Chem. Res. 35 (2002) 209-217
6. Selected examples include:. Wilson M.E., and Whitesides G.M. J. Am. Chem. Soc. 100 (1978) 306-307
7. Ohashi M., Koshiyama T., Ueno T., Yanase M., Fujii H., and Watanabe Y. Angew. Chem., Int. Ed. 42 (2003) 1005-1008
8. Collot J., Gradinaru J., Humbert N., Skander M., Zocchi A., and Ward T.R. J. Am. Chem. Soc. 125 (2003) 9030-9031
9. Carey J.R., Ma S.K., Pfister T.D., Garner D.K., Kim H.K., Abramite J.A., Wang Z., Guo Z., and Lu Y. J. Am. Chem. Soc. 126 (2004) 10812-10813
10. Reetz M.T., and Jiao N. Angew. Chem., Int. Ed. 45 (2006) 2416-2419
11. Pierron J., Malan C., Creus M., Gradinaru J., Hafner I., Ivanova A., Sardo A., and Ward T.R. Angew. Chem., Int. Ed. 47 (2008) 701-705
12. For a review see. Steinreiber J., and Ward T.R. Coord. Chem. Rev. 252 (2008) 751-766
13. Ropartz L., Meeuwenoord N.J., Van der Marel J.A., Van Leeuwen P.W.N.M., Slawin A.M.Z., and Kamer P.C.J. Chem. Commun. (2007) 1556-1558
14. For a review, see:. Roelfes G. Mol. Biosyst. 3 (2007) 126-135
15. Roelfes G., and Feringa B.L. Angew. Chem., Int. Ed. 44 (2005) 3230-3232
16. Roelfes G., Boersma A.J., and Feringa B.L. Chem. Commun. (2006) 635-637
17. Boersma A.J., Feringa B.L., and Roelfes G. Org. Lett. 9 (2007) 3647-3650
18. Coquière D., Feringa B.L., and Roelfes G. Angew. Chem., Int. Ed. 46 (2007) 9308-9311
19. Shibata N., Yasui H., Nakamura S., and Toru T. Synlett (2007) 1153-1157
20. Kagan H.B., and Fiaud J.C. Kinetic Resolution. In: Eliel E.L., and Fiaud J.C. (Eds). Topics in Stereochemistry Vol. 18 (1988), John Wiley, New York 249-330
21. Ghanem A. Tetrahedron 63 (2007) 1721-1754
22. Vedejs E., and Jure M. Angew. Chem., Int. Ed. 44 (2005) 3974-4001
23. Faber K. Biotransformations in Organic Chemistry: A Textbook. 4th ed. (2000), Springer, Berlin
24. Tokunaga M., Larrow J.F., Kakiuchi F., and Jacobsen E.N. Science 277 (1997) 936-938
25. Schaus S.E., Brandes B.D., Larrow J.F., Tokunaga M., Hansen K.B., Gould A.E., Furrow M.E., and Jacobsen E.N. J. Am. Chem. Soc. 124 (2002) 1307-1315
26. Jacobsen E.N. Acc. Chem. Res. 33 (2000) 421-431
27. Lutje Spelberg J.H., Rink R., Kellogg R.M., and Janssen D.B. Tetrahedron: Asymmetry 9 (1998) 459-466
28. Chen X.-J., Archelas A., and Furstoss R. J. Org. Chem. 58 (1993) 5528-5532
29. Genzel Y., Archelas A., Broxterman Q.B., Schulze B., and Furstoss R. J. Org. Chem. 66 (2001) 538-543
30. For reviews, see:. Archelas A., and Furstoss R. Curr. Opin. Chem. Biol. 5 (2001) 112-119
31. De Vries E.J., and Janssen D.B. Curr. Opin. Biotechnol. 14 (2003) 414-420
32. Monodentate epoxide substrates, such as styrene oxide, could not be resolved using our approach. Enantiomeric enrichment of styrene oxide was not observed upon submission to the reaction conditions. Presumably, styrene oxide can not successfully compete with water in the coordination to the DNA-bound metal ion. See also Ref. 5c.
33. Hanzlik R.P., and Hamburg A. J. Am. Chem. Soc. 100 (1978) 1745-1749
34. Hanzlik R.P., Edelman M., Michaely W.J., and Scott G. J. Am. Chem. Soc. 98 (1976) 1952-1955
35. Solladié-Cavallo A., Lupattelli P., Marsol C., Isarno T., Bonini C., Caruso L., and Maiorella A. Eur. J. Org. Chem. (2002) 1439-1444
36. Copper was shown not to bind MOPS; see:. Mash H.E., Chin Y.-P., Sigg L., Hari R., and Xue H. Anal. Chem. 75 (2003) 671-677
37. 22 = + 285 (c 1, EtOH)
38. Berti G., Bottari F., Macchia B., and Nuti V. Ann. Chim. (Rome) 54 (1964) 1253-1265
39. Forrester J., Jones R.V.H., Newton L., and Preston P.N. Tetrahedron 57 (2001) 2871-2884
40. Berti G., Bottari F., Lippi G., and Macchia B. Tetrahedron 24 (1968) 1959-1971
41. Xiao L., and Johnson K.E. Can. J. Chem. 82 (2004) 491-498