Teaching old indicators new tricks: A colorimetric chemosensing ensemble for tartrate/malate in beverages

Angewandte Chemie - International Edition

Volumn 38, Issue 24, 1999, Pages 3666-3669

  Lavigne, John J ^a   Anslyn, Eric V ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

Analytical methods; Boron; Molecular recognition; Sensors; Tartrate

Indexed keywords

MALIC ACID; TARTARIC ACID;

ABSORPTION SPECTROPHOTOMETRY; ARTICLE; BEVERAGE; CALIBRATION; CHEMICAL BINDING; COLORIMETRY; FLUORESCENCE; MOLECULAR RECOGNITION; SIGNAL TRANSDUCTION; STRUCTURE ANALYSIS;

EID: 0033576731     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19991216)38:24<3666::AID-ANIE3666>3.0.CO;2-E     Document Type: Article

References (49)

1. a) S. Miltsov, C. Encinas, J. Alonso, Tetrahedron Lett. 1998, 39, 9253-9254;
2. b) F. J. Green, The Sigma-Aldrich Handbook of Stains, Dyes and Indicators, Aldrich Chemical Company, Milwaukee, 1991.
3. a) R. Pribil, Analyst 1958, 83, 188-195;
4. b) K. Kimura, M. Sumida, M. Yokoyama, Chem. Commun. 1997, 1417-1418;
5. c) T. H. Schrader, Tetrahedron Lett. 1998, 39, 517-520.
6. a) J. L. Lambert, O. T. Fina, E. F. Dikeman, Anal. Chem. 1982, 54, 828-830, and references therein;
7. b) F. P. Schmidtchen, M. Berger, Chem. Rev. 1997, 97, 1609-1646.
8. D. A. Becker, J. Am. Chem. Soc. 1996, 118, 905-906.
9. a) L. B. Bangs, Pure Appl. Chem. 1996, 68, 1873-1879;
10. b) A. Dzgoev, M. Mecklenburg, P.-O. Larsson, B. Danielsson, Anal. Chem. 1996, 68, 3364-3369;
11. c) O. A. Sadik, J. M. Van Emon, CHEMTECH 1997, 27, 38-46.
12. a) O. X. Li, M. S. Zhao, S. J. Gee, M. J. Kurth, J. N. Seiber, B. D. Hammock, J. Agric. Food Chem. 1991, 39, 1685-1692;
13. b) M. A. Roberts, R. A. Durst, Anal. Chem. 1995, 67, 482-491;
14. c) C. Beyer, I. H. Alting, Clin. Chem. 1996, 42, 313-318.
15. a) A. Metzger, E. V. Anslyn, Angew. Chem. 1998, 110, 682-684; Angew. Chem. Int. Ed. 1998, 37, 649-652;
16. a) A. Metzger, E. V. Anslyn, Angew. Chem. 1998, 110, 682-684; Angew. Chem. Int. Ed. 1998, 37, 649-652;
17. b) K. Niikura, A. Metzger, E. V. Anslyn, J. Am. Chem. Soc. 1998, 120, 8533-8534;
18. c) K. N. Koh, K. Araki, A. Ikeda, H. Otsuka, S. Shinkai, J. Am. Chem. Soc. 1996, 118, 755-758.
19. J. P. Lorand, J. O. Edwards, J. Org. Chem. 1959, 24, 769-774.
20. a) R. P. Dixon, S. J. Geib, A. D. Hamilton, J. Am. Chem. Soc. 1992, 114, 365-366;
21. b) A. Metzger, V. M. Lynch, E. V. Anslyn, Angew. Chem. 1997, 109, 911-914; Angew. Chem. Int. Ed. Engl. 1997, 36, 862-865.
22. b) A. Metzger, V. M. Lynch, E. V. Anslyn, Angew. Chem. 1997, 109, 911-914; Angew. Chem. Int. Ed. Engl. 1997, 36, 862-865.
23. For further references that combine boronic acids with other molecular recognition motifs, see a) M.-F. Paugam, L. S. Valencia, B. Boggess, B. D. Smith, J. Am. Chem. Soc. 1994, 116, 11203-11204;
24. b) C. R. Cooper, T. D. James, Chem. Commun. 1997, 1419-1420;
25. c) S. Patterson, B. D. Smith, R. E. Taylor, Tetrahedron Lett. 1997, 38, 6323-6236;
26. d) M. Yamamoto, M. Takeuchi, S. Shinkai, Tetrahedron 1998, 54, 3125-3140.
27. a) K. V. Kilway, J. S. Siegel, J. Am. Chem. Soc. 1992, 114, 255-261;
28. b) D. J. Iverson, G. Hunter, J. F. Blount, J. R. Damewood, K. Mislow, J. Am. Chem. Soc. 1981, 103, 6073-6083;
29. c) H.-W. Marx, F. Moulines, T. Wagner, D. Astruc, Angew. Chem. 1996, 108, 1842-1845; Angew. Chem. Int. Ed. Engl. 1996, 35, 1701-1704.
30. c) H.-W. Marx, F. Moulines, T. Wagner, D. Astruc, Angew. Chem. 1996, 108, 1842-1845; Angew. Chem. Int. Ed. Engl. 1996, 35, 1701-1704.
31. a) T. D. James, K. R. A. S. Sandanayake, S. Shinkai, J. Chem. Soc. Chem. Commun. 1994, 477-478;
32. b) T. D. James, K. R. A. S. Sandanayake, R. Iguchi, S. Shinkai, J. Am. Chem. Soc. 1995, 117, 8982-8987;
33. K. R. A. S. Sandanayake, T. D. James, S. Shinkai, Chem. Lett. 1995, 503-504.
34. K. R. A. S. Sandanayake, S. Shinkai, J. Chem. Soc. Chem. Commun. 1994, 1083-1084.
35. a) R. T. Hawkins, H. R. Snyder, J. Am. Chem. Soc. 1960, 82, 3863-3866;
36. b) R. T. Hawkins, A. U. Blackham, J. Org. Chem. 1967, 32, 597-600;
37. c) V. S. Bogdanov, V. G. Kiselev, A. D. Naumov, L. S. Vasil'ev, V. P. Dmitrikov, V. A. Dorokhov, B. M. Mikhailov, J. Gen. Chem. USSR 1973, 43, 1539-1544;
38. d) T. Burgemeister, R. Grobe-Einsler, R. Grotstollen, A. Mannschreck, G. Wulff, Chem. Ber. 1981, 114, 3403-3411.
39. a) R. Contreras, C. Garcia, T. Mancilla, J Organomet. Chem. 1983, 246, 213-217;
40. b) P. M. Gallop, M. A. Paz, E. Henson, Science 1982, 217, 166-169;
41. c) R. Csuk, H. Honig, C. Romanin, Monatsh. Chem. 1982, 113, 1025-1035. For more interesting examples, see
42. d) L. K. Mohler, A. W. Czarnik, J. Am. Chem. Soc. 1993, 115, 7037-7038;
43. e) T. Mancilla, R. Contreras, B. Wrackmeyer, J. Organomet. Chem. 1986, 307, 1-6;
44. f) T. Mancilla, R. Contreras, J. Organomet. Chem. 1987, 321, 191-198.
45. H. Noth, B. Wrackmeyer in Nuclear Magnetic Resonance Spectroscopy of Boron Compounds, Vol. 14 (Eds.: P. Diehl, E. Fluck, R. Kosfeld), Springer, Berlin, 1978.
46. M. A. Leonard, T. S. West, J. Chem. Soc. 1960, 4477-4485.
47. R. Belcher, M. A. Leonard, T. S. West, J. Chem. Soc. 1958, 2390-2393.
48. K. A. Connors, Binding Constants. The Measurement of Molecular Complex Stability, Wiley, New York, 1987.
49. D. M. Perreault, Ph.D. thesis, University of Texas, Austin, TX (USA), 1997.