A colorimetric ligand for mercuric ion

Organic Letters

Volumn 1, Issue 3, 1999, Pages 415-418

  Brümmer, Oliver ^a   La Clair, James J ^a   Janda, Kim D ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0038004382     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990730f     Document Type: Article

References (38)

1. (a) Shotyk, W.; Weiss, D.; Appleby, P. G.; Cheburkin, A. K.; Frei, R.; Gloor, J. D.; Kramers, M.; Reese, S.; Vanderknaap, W. O. Science 1998, 281, 1635.
2. (b) Benoit, J. M.; Fitzgerald, W. F.; Damman, A. W. Environ. Res. 1998, 78, 118.
3. McKeown-Eyssen, G. E.; Ruedy, J. Am. J. Epidemiol. 1983, 118, 461.
4. Harada, M. Crit. Rev. Toxicol. 1995, 25, 1.
5. (e) Renzoni, A.; Zino, F.; Franchi, E. Environ. Res. 1998, 77, 68.
6. (a) Nendza, M.; Herbst, T.; Kussatz, C.; Gies, A. Chemosphere 1997, 35, 1875.
7. (b) Boudou, A.; Ribeyre, F. Metal Ions Biol. Systems 1997, 34, 289.
8. Clarkson, T. W. Am. J. Clin. Nutrit. 1995, 61, 682S.
9. For mercuric ion sensitive fluorescent probes, see: (a) Sasaki, D. Y.; Padilla, B. E. Chem. Commun. 1998, 1581.
10. (b) Hennrich, G.; Sonnenschein, H.; Resch-Genger, U. J. Am. Chem. Soc. 1999, 121, 5073 and references therein.
11. For other methods to detect mercury, see: (a) Uria, J. E. S.; Sanzmedel, A. Talanta 1998, 47, 509.
12. (b) Krenkel, P. A. in Heavy metals in the aquatic environment; Pergamon Press: Oxford, 1997.
13. Wagemann, R.; Trebacz, E.; Boila, G.; Lockhart, W. L. Science Total Environ. 1998, 218, 19.
14. Moreton, J. A.; Delves, H. T. J. Anal. At. Spectrom. 1998, 13, 659.
15. (e) Hardy, S.; Jones, P. J. Chrom. A. 1997, 791, 333.
16. (f) Flamini, A.; Panusam, A. Sens. Actuators 1997, B42, 39.
17. For fluorescent sensors that monitor metal binding in general, see: (a) Walkup, G. K.; Imperiali, B. J. Org. Chem. 1998, 63, 6727.
18. (b) Walkup, G. K.; Imperiali, B. J. Am. Chem. Soc. 1997, 119, 3443.
19. Yoon, J. Y.; Ohler, N. E.; Vance, D. H.; Aumiller, W. D.; Czarnik, A. W. Tetrahedron Lett. 1997, 38, 3845.
20. Kimura, M.; Horai, T.; Hanabusa, K.; Shirai, H. Adv. Mater. 1998, 10, 459.
21. (e) Corradini, R.; Dossena, A.; Galaverna, G.; Marchelli, R.; Panagia, A.; Sartor, G. J. Org. Chem. 1997, 62, 6283.
22. (g) Desantis, G.; Fabbrizzi, L.; Licchelli, M.; Mangano, C.; Sacchi, D.; Sardone, N. Inorg. Chim. Acta 1997, 257, 69.
23. Hauze, D.; Joullié, M. M. Tetrahedron 1997, 53, 4239.
24. (a) Bastian, L. A.; Piscitelli, J. T. JAMA 1998, 279, 1264.
25. (b) Bose, R. J. Assist. Reproduct. Gen. 1997, 14, 497.
26. Alfthan, H.; Stenman, U. H. Cell. Endocrinol. 1996, 125, 107.
27. Woidich, H.; Pfannhauser, W. Z. Lebensm. Unters. Forsch. 1972, 149, 1.
28. For metal binding to phosphorodithioates, see: Hayashi, K.; Sasaki, Y.; Tagashira, S.; Yanagidani, T. Bull. Chem. Soc. Jpn. 1986, 59, 1255.
29. Reichardt, C. Chem. Rev. 1994, 94, 2319.
30. Brümmer, O.; Gao, C.; Mao, S.; Weiner, D. P.; Janda, K. D. Lett. Pept. Sci. 1999, in press. For the synthesis of phosphorodithioates, see also: Martin, S. F.; Wagman, A. S. J. Org. Chem. 1996, 61, 8016.
31. Brümmer, O.; Gao, C.; Mao, S.; Weiner, D. P.; Janda, K. D. Lett. Pept. Sci. 1999, in press. For the synthesis of phosphorodithioates, see also: Martin, S. F.; Wagman, A. S. J. Org. Chem. 1996, 61, 8016.
32. For general metal ligand interactions, see: O'Sullivan, W. J.; Smithers, G. W. In Methods in Enzymology; Purich, D. L., Ed.; Academic Press: New York, 1979; pp 294-336.
33. (a) La Clair, J. J. J. Am. Chem. Soc. 1997, 119, 7676.
34. (b) La Clair, J. J. Angew. Chem., Int. Ed. Engl. 1998, 37, 325.
35. (a) Lawton, S. L. Inorg. Chem. 1971, 10, 328.
36. (b) Burn, A. J.; Dewan, S. K.; Gosney, I.; McKendrick, K. G.; Warrens, C. P.; Wastle, J. P.; Watson, C. W. J. Chem. Soc., Perkin Trans. 2 1994, 373.
37. Metal ions also form a variety of higher order complexes in both metal and ligand with phosphorodithiolates. While spectroscopic and mass determinations indicate that the precipitation under the given conditions resulted in a 2:1 dye to metal complex, complete precipitation also occurs with far more metal per ligand. For reports describing the formation and precipitation of such complexes, see: (a) Drew, M. G. B.; Hobson, R. J.; Mumba, P. P. E. M.; Rice, D. A. J. Chem. Soc., Dalton Trans. 1987, 1569.
38. (b) Dakternieks, D. R.; Graddon, D. P. Aust. J. Chem. 1971, 24, 2077.