Synthesis and Hydrolysis Monitoring of Sasrin-like Resin Bound Imines by Fluorescence Spectroscopy

Authors

  • Domingo Madrigal Instituto Tecnológico de Tijuana
  • Georgina Pina-Luis Instituto Tecnológico de Tijuana
  • Ignacio A. Rivero Instituto Tecnológico de Tijuana

Keywords:

Fluorescence spectroscopy, monitoring reaction, solid phase

Abstract

Abstract. Merrifield resin was converted to various dialkyl-trihydroxybenzaldehyde resins and then to different bound imine resins. Fluorescence spectroscopy was used to continuously monitor the intermediates performed on the resins. Using fluorescent label (dansyl chloride) information on the kinetics of the amine cleavage was obtained. This study demonstrated that direct measures of fluorescence intensity on single-resin beads can be an effective method of monitoring solid phase organic reactions.

Resumen. Se empleó resina de Merrifield para obtener varias resinas con grupos de trihidroxibenzaldehido dialquilados y posteriormente se obtuvieron las correspondientes iminas. Los intermediarios formados sobre las resinas fueron monitoreados usando espectroscopia de fluorescencia. Se obtuvo la cinética de liberación de la amina usando un indicador fluorescente (cloruro de dansilo). Este estudio sugiere que la intensidad de fluorescencia obtenida por medida directa desde una muestra de resina puede ser un método eficiente para monitorear reacciones en fase sólida.

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Author Biographies

Domingo Madrigal, Instituto Tecnológico de Tijuana

Centro de Graduados e Investigación

Georgina Pina-Luis, Instituto Tecnológico de Tijuana

Centro de Graduados e Investigación

Ignacio A. Rivero, Instituto Tecnológico de Tijuana

Centro de Graduados e Investigación

References

1. Yan, B.; Gstach, H. Tetrahedron Lett. 1996, 37, 8325-8328
2. Gosselin, F.; Di Renzo, M.; Ellis, T.H.; Lubell, W.D. J. Org. Chem. 1996, 61, 7980-7981
3. Shapiro, M.J.; Gounarides, J.S. Prog. Nucl. Magn. Reson. Spect. 1999, 35, 153-200
4. Stöver, H.D.; Fréchet, J.M. Macromolecules, 1989, 22, 1574-1576
5. Taylor, E.V.; Qian, M.G.; Dollinger, G.D. Anal. Chem. 1998, 70, 3339-3347
6. Yan, B.; Li, W. J. Org. Chem. 1997, 62, 9354-9357
7. Yan, B.; Martin, P.C.; Lee, J. J. Comb. Chem. 1999, 1, 78-81
8. Chu, S. S.; Reich, S. H. Bioorg. Med. Lett. 1995, 5, 1053. Shapiro, M. J.: Kumaravel, G.; Setter, R. C.; Beveridge, R. Tetrahedron Lett. 1996, 37, 4671-4674
9. Kaldor, S.W.; Seigel, M.G.; Fritz, J.E.; Dressman, B.A.; Hahn, P.J. Tetrahedron Lett. 1996, 37, 7193-7196
10. Frechet, J.M.; Schuerch, C. J. Am. Chem. Soc. 1971, 93, 492-496
11. Mergler, M.; Taner, R; Gosteli, J.; Grogg, P. Tetrahedron Lett. 1988, 29, 4005-4008. Larsson, E.; Lüning, B. Tetrahedron Lett. 1994, 35, 2737-2738
12. Guiles, J. W.; Johnson, S. G.; Murria, W. V. J. Org. Chem. 1996, 61, 5169-5171
13. Pina-Luis, G.; Badía, R.; Díaz-García, M.E.; Rivero, I.A. J. Comb. Chem. 2004, 6, 391-397
14. Rivero, I. A.; González, T.; Pina-Luis, G. J. Comb. Chem. 2005, 6, 46-53
15. Rivero, I. A.; Peralta, M.; Heredia. S.; Madrigal, D.; Pina-Luis, G. Arkivoc, 2003, (xi), 27-36
16. Castillo, M.; Pina-Luis, G.; Diaz-Garcia, M. E.; Rivero, I. A. J. Braz. Chem. Soc. 2005, 16 (3A), 412-417
17. Rivero I.A.; González T.; Díaz-García M.E. Comb. Chem.& High Throughput Screening, 2006, 9(7), 535-544
18. Stewart, J. M.; Young, J. D. Solid Phase Peptide Synthesis, 1969, W. H. Freeman, San Francisco
19. Reaction of 1 with the model compound benzylchloride instead of the Merrifield resin, in THF resulted in a 8:2 para:ortho ratio mixture of substituted benzyl, which was characterized as follows. 1H-NMR (DMSO, 200 MHz): d 10.02 (20%) and 10.09 (80 %) ppm, CHO. Laibinis [17], found an 9:1 ratio of para- to ortho-substituted products.
20. Chávez, D.; Ochoa, A.; Madrigal, D.; Castillo, M.; Espinoza, K.; González, T.; Vélez, E.; Meléndez, J.; García, J. D.; Rivero, I. A. J. Comb. Chem. 2003, 5, 149-154
21. Yan B.; Fell J. B.; Kumaravel, G. J. Org. Chem. 1996, 61, 7467- 7472.
22. Kress, J.; Zanaletti, R.; Rose, A; Frey, G. J.; Brocklesby, W. S.; Ladlow, M; Bradley, M. J. Comb. Chem. 2003, 5, 28-32.

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Published

2020-08-05

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