NMR spectral enantioresolution of spirobrassinin and 1-methoxyspirobrassinin enantiomers using (S)-(-)-ethyl lactate and modeling of spirobrassinin self-association for rationalization of its self-induced diastereomeric anisochromism (SIDA) and enantiomer self-disproportionation on achiral-phase chromatography (ESDAC) phenomena

Journal of Fluorine Chemistry

Volumn 131, Issue 4, 2010, Pages 467-476

  Klika, Karel D ^a   Budovská, Mariana ^a,b   Kutschy, Peter ^b  

^a UNIVERSITY OF TURKU   (Finland)

^b P J AFÁRIK UNIVERSITY   (Slovakia)

Author keywords

DFT calculations; Enantiodifferentiation; NMR; Self disproportionation of enantiomers; Spirobrassinin

Indexed keywords

EID: 77949492203     PISSN: 00221139     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jfluchem.2009.10.018     Document Type: Article

References (56)

1. Dixon R.A., and Lamb C. J. Ann. Rev. Plant Physiol. Plant Mol. Biol. 41 (1990) 339-367
2. Rouxel T., Kollman A., and Belesdent M.H. In: Daniel M., and Purkayastha R.P. (Eds). Handbook of Phytoalexin Metabolism and Action (1995), Marcel Dekker, New York 229-261
3. Pedras M.S.C., Okanga F.I., Zaharia I.L., and Khan A.Q. Phytochemistry 53 (2000) 161-176
4. Mehta R.G., Liu J., Constantinou A., Hawthorne M., Pezzuto J.M., Moon R.C., and Moriarty R.M. Anticancer Res. 14 (1994) 1209-1214
5. Mehta R.G., Liu J., Constantinou A., Thomas C.F., Hawthorne M., You M., Gerhauser C., Pezzuto J.M., Moon R.C., and Moriarty R.M. Carcinogenesis 16 (1995) 399-404
6. Sabol M., Kutschy P., Siegfried L., Miroššay A., Suchý M., Hrbková H., Dzurilla M., Marušková R., Starková J., and Paulíková E. Biologia 55 (2000) 701-707
7. Moody C.J., Roffey J.R.A., Stephens M.A., and Stradford I.J. Anti-Cancer Drugs 8 (1997) 489-499
8. Pilátová M., Sariššký M., Kutschy P., Miroššay A., Mezencev R., Čurillová Z., Suchý M., Monde K., Miroššay L., and Mojžiš J. Leuk. Res. 29 (2005) 415-421
9. Mezencev R., Mojžiš J., Pilátová M., and Kutschy P. Neoplasma 50 (2003) 239-245
10. Crossley R. Chirality and the Biological Activity of Drugs (1995), CRC Press, Boca Raton, FL
11. The recommendation of R.E. Gawley, J. Org. Chem. 71 (2006) 2411-2416 is followed with regards to the preferential use of enantiomer % over enantiomeric excess (e.e.).
12. Aboul-Enein H.Y., and Ali I. Chiral Separations by Liquid Chromatography and Related Technologies (2003), Marcel Dekker, New York
13. In: Subramanian G. (Ed). Chiral Separation Techniques: A Practical Approach. third ed. (2007), Wiley-VCH, Weinheim
14. Pirkle W.H., and Hoover D.J. Top. Stereochem. 13 (1982) 263-331
15. Wenzel T.J., and Wilcox J.D. Chirality 15 (2003) 256-270
16. Parker D. Chem. Rev. 91 (1991) 1441-1457
17. Wenzel T.J. Discrimination of Chiral Compounds Using NMR Spectroscopy (2007), Wiley-VCH, Weinheim
18. Nieminen V., Murzin D.Yu., and Klika K.D. Org. Biomol. Chem. 7 (2009) 537-542
19. K.D. Klika, unpublished results.
20. Soloshonok V.A. Angew. Chem. Int. Ed. 45 (2006) 766-769 and 13 other original references cited therein concerning the ESDAC phenomenon
21. Stephani R., and Cesare V.J. J. Chromatogr. A 813 (1998) 79-84
22. Carman R.M., and Klika K.D. Aust. J. Chem. 44 (1991) 895-896
23. Soloshonok V.A., and Berbasov D.O. J. Fluor. Chem. 127 (2006) 597-603
24. A review of the phenomenon is given by J. Martens, R. Bhushan, J. Liq. Chromatogr. Relat. Technol. 15 (1992) 1-27.
25. Reference [14] provides a listing of 8 references treating the topic.
26. Soloshonok V.A., and Berbasov D.O. Chim. Oggi-Chem. Today 24 (2006) 44-47
27. Takasugi M., Monde K., Katsui N., and Shirata A. Chem. Lett. (1987) 1631-1632
28. Suchý M., Kutschy P., Monde K., Goto H., Harada N., Takasugi M., Dzurilla M., and Balentová E. J. Org. Chem. 66 (2001) 3940-3947
29. Gross D., Porzel A., and Schmidt J. Z. Naturforsch. (C) 49 (1994) 281-285
30. Kutschy P., Suchý M., Monde K., Harada N., Marušková R., Čurillová Z., Dzurilla M., Miklošová M., Mezencev R., and Mojžiš J. Tetrahedron Lett. 43 (2002) 9489-9492
31. Čurillová Z., Kutschy P., Budovská M., Nakahashi A., and Monde K. Tetrahedron Lett. 48 (2007) 8200-8204
32. Monde K., Taniguchi T., Miura N., Kutschy P., Čurillová Z., Pilátová M., and Mojžiš J. Bioorg. Med. Chem. 13 (2005) 5206-5212
33. Pedras M.S.C., Hossain M., Sarwar M.G., and Montaut S. Bioorg. Med. Chem. Lett. 14 (2004) 5469-5471
34. Klika K.D., Kramer M., and Kleinpeter E. Theochem. J. Mol. Struct. 913 (2009) 247-253
35. Stonehouse J., Adell P., Keeler J., and Shaka A.J. J. Am. Chem. Soc. 116 (1994) 6037-6038
36. Stott K., Stonehouse J., Keeler J., Hwang T.L., and Shaka A.J. J. Am. Chem. Soc. 117 (1995) 4199-4200
37. Virta P., Koch A., Roslund M.U., Mattjus P., Kleinpeter E., Kronberg L., Sjöholm R., and Klika K.D. Org. Biomol. Chem. 3 (2005) 2924-2929
38. Balentová E., Imrich J., Bernát J., Suchá L., Vilková M., Prónayová N., Kristian P., Pihlaja K., and Klika K.D. J. Heterocycl. Chem. 43 (2006) 645-656
39. Fröhlichová Z., Imrich J., Danihel I., Kristian P., Böhm S., Sabolová D., Kožurková M., Hritzová O., Horváth B., Bušová T., and Klika K.D. Spectroc. Acta Pt. A 73 (2009) 238-248
40. Mäki J., Tähtinen P., Kronberg L., and Klika K.D. J. Phys. Org. Chem. 18 (2005) 240-249
41. See for example: R. Laatikainen, M. Niemitz, U. Weber, J. Sundelin, T. Hassinen, J. Vepsäläinen, J. Magn. Reson. Ser. A 120 (1996) 1-10; see also: Peak Research NMR Software, Perch Solutions Ltd., Kuopio, Finland, 2003 (http://www.perchsolutions.com).
42. Becke A.D. J. Chem. Phys. 98 (1993) 5648-5652
43. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Montgomery Jr. J.A., Vreven T., Kudin K.N., Burant J.C., Millam J.M., Iyengar S.S., Tomasi J., Barone V., Mennucci B., Cossi M., Scalmani G., Rega N., Petersson G.A., Nakatsuji H., Hada M., Ehara M., Toyota K., Fukuda R., Hasegawa J., Ishida M., Nakajima T., Honda Y., Kitao O., Nakai H., Klene M., Li X., Knox J.E., Hratchian H.P., Cross J.B., Bakken V., Adamo C., Jaramillo J., Gomperts R., Stratmann R.E., Yazyev O., Austin A.J., Cammi R., Pomelli C., Ochterski J.W., Ayala P.Y., Morokuma K., Voth G.A., Salvador P., Dannenberg J.J., Zakrzewski V.G., Dapprich S., Daniels A.D., Strain M.C., Farkas O., Malick D.K., Rabuck A.D., Raghavachari K., Foresman J.B., Ortiz J.V., Cui Q., Baboul A.G., Clifford S., Cioslowski J., Stefanov B.B., Liu G., Liashenko A., Piskorz P., Komaromi I., Martin R.L., Fox D.J., Keith T., Al-Laham M.A., Peng C.Y., Nanayakkara A., Challacombe M., Gill P.M.W., Johnson B., Chen W., Wong M.W., Gonzalez C., and Pople J.A. Gaussian03, Revision D. 02 (2003), Gaussian, Inc., Wallingford, CT
44. Becke A.D. Phys. Rev. A 38 (1988) 3098-3100
45. Lee C., Yang W., and Parr R.G. Phys. Rev. B 37 (1988) 785-789
46. Miehlich B., Savin A., Stoll H., and Preuss H. Chem. Phys. Lett. 157 (1989) 200-206
47. Scott A.P., and Radom L. J. Phys. Chem. 100 (1996) 16502-16513
48. Wolinski K., Hinton J.F., and Pulay P. J. Am. Chem. Soc. 112 (1990) 8251-8260
49. And also accepting that the slight splitting observed on a few signals would not be evident with typical acquisition conditions and parameters with regards to field homogeneity ("shim"), acquired resolution and processing.
50. Mäki J., Klika K.D., Sjöholm R., and Kronberg L. J. Chem. Soc., Perkin Trans. 1 (2001) 1216-1219
51. Alei M., Morgan L.O., Wagerman W.E., and Whaley T.M. J. Am. Chem. Soc. 102 (1980) 2881-2887
52. Bagno A., and Scorrano G. Acc. Chem. Res. 33 (2000) 609-616
53. Klika K.D., Balentová E., Bernát J., Imrich J., Vavrušová M., Kleinpeter E., Pihlaja K., and Koch A. J. Heterocycl. Chem. 43 (2006) 633-643
54. Klika K.D., Balentová E., Bernát J., Imrich J., Vavrušová M., Pihlaja K., Koch A., Kleinpeter E., Kelling A., and Schilde U. ARKIVOC xvi (2006) 93-108
55. Böhm S., Tomaščiková J., Imrich J., Danihel I., Kristian P., Koch A., Kleinpeter E., and Klika K.D. Theochem. J. Mol. Struct. 916 (2009) 105-118
56. Klika K.D. Tetrahedron Asym. 20 (2009) 1099-1102