High-affinity pyrophosphate receptor by a synergistic effect between metal coordination and hydrogen bonding in water

Organic Letters

Volumn 9, Issue 19, 2007, Pages 3729-3731

  Lee, Jae Han ^a   Park, Jaejoon ^b   Lah, Myoung Soo ^b   Chin, Jik ^c   Hong, Jong In ^a  

^a Seoul National University   (South Korea)

^b Hanyang University   (South Korea)

^c UNIVERSITY OF TORONTO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

PHOSPHATE; WATER; ZINC;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; HYDROGEN BOND; METABOLISM; SOLUTION AND SOLUBILITY; SPECTROPHOTOMETRY; X RAY CRYSTALLOGRAPHY;

CRYSTALLOGRAPHY, X-RAY; HYDROGEN BONDING; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PHOSPHATES; SOLUTIONS; SPECTROPHOTOMETRY; WATER; ZINC;

EID: 34848817693     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol071306e     Document Type: Article

References (35)

1. (a) Limpcombe, W. N.; Sträter, N. Chem. Rev. 1996, 96, 2375.
2. (b) Nyrén, P. Anal. Biochem. 1987, 167, 235-238.
3. (c) Tabary, T.; Ju, L. J. Immunol. Methods 1992, 156, 55-60.
4. (a) Doherty, M.; Belcher, C.; Regan, M.; Jones, A.; Ledingham, J. Ann. Rheum. Dis. 1996, 55, 432-436.
5. (b) Timms, A. E.; Zhang, Y.; Russell R. G.; Brown, M. A. Rheumatology 2002, 41, 725-729.
6. PPi sensors in aqueous solution: (a) Vance, D. H.; Czarnik, A. W. J. Am. Chem. Soc. 1994, 116, 9397-9398.
7. (b) Czarnik, A. W. Acc. Chem. Res. 1994, 27, 302-308.
8. (c) Mizukami, S.; Nagano, T.; Urano, Y.; Odani, A.; Kikuchi, K. J. Am. Chem. Soc. 2002, 124, 3920-3925.
9. (d) Fabbrizzi, L.; Marcotte, N.; Stomeo, F.; Taglietti, A. Angew. Chem., Int. Ed. 2002, 41, 3811-3814.
10. (e) Lee, D. H.; Im, J. H.; Son, S. U.; Chung, Y. K.; Hong, J.-I. J. Am. Chem. Soc. 2003, 125, 7752-7753.
11. (f) Lee, D. H.; Kim, S. Y.; Hong, J.-I. Angew. Chem., Int. Ed. 2004, 43, 4777-4780.
12. (g) Cho, H. K.; Lee. D. H.; Hong, J.-I. Chem. Commun. 2005, 1690-1692.
13. (h) Jang, Y. J.; Jun, E. J.; Lee, Y. J.; Kim, Y. S.; Kim, J. S.; Yoon, J. J. Org. Chem. 2005, 70, 9603-9606.
14. (i) Lee, H. N.; Xu, Z.; Kim, S. K.; Swamy, K. M. K.; Kim, Y.; Kim, S.-J.; Yoon, J. J. Am. Chem. Soc. 2007, 129, 3828-3829.
15. (j) Lee, H. N.; Swamy, K. M. K.; Kim, S. K.; Kwon, J.-Y.; Kim, Y.; Kim, S.-J.; Yoon, Y. J.; Yoon, J. Org. Lett. 2007, 9, 243-246.
16. (k) Aldakov, D.; Anzenbacher, P., Jr. J. Am. Chem. Soc. 2004, 126, 4752-4753.
17. 3CN: (a) Nishizawa, S.; Kato, Y.; Teramae, N. J. Am. Chem. Soc. 1999, 121, 9463-9464.
18. (b) Anzenbacher, P., Jr.; Jursíková, K.; Sessler, J. L. J. Am. Chem. Soc. 2000, 122, 9350-9351.
19. (a) Mancin, F.; Chin, J. J. Am. Chem. Soc. 2002, 124, 10946-10947.
20. (b) Chin, J.; Chung, S.; Kim, D. H. J. Am. Chem. Soc. 2002, 124, 10948-10949.
21. (c) Wall, M.; Linkletter, B.; Williams, D.; Lebuis, A.; Hynes, R. C.; Chin, J. J. Am. Chem. Soc. 1999, 121, 4710-4711.
22. (a) Suzuki, M.; Kanatomi, H.; Murase, I. Chem. Lett. 1981, 1745-1748.
23. (b) Munch, B. P.; Bradley, F. C.; Boyle, P. D.; Papaefthymiou, V.; Que, L., Jr. J. Am. Chem. Soc. 1987, 109, 7993-8003.
24. (c) Jin, S. S.; Sung, N. D.; Hynes, R. C.; Chin, J. Inorg. Chem. 1996, 35, 7472-7473.
25. (d) Torelli, S.; Belle, C.; Gautier-Luneau, I.; Pierre, J. L.; Saint-Aman, E.; Latour, J. M.; Le Pape, L.; Luneau, D. Inorg. Chem. 2000, 39, 3526-3536.
26. (e) Han, M. S.; Kim, D. H. Angew. Chem., Int. Ed. 2002, 41, 3809-3811.
27. (f) Molenveld, P.; Engbersen, J. F. J.; Reinhoudt, D. N. Chem. Soc. Rev. 2000, 29, 75-86.
28. Karlin, K. D.; Gultneh, Y.; Nicholson, T.; Zubieta, J. Inorg. Chem. 1985, 24, 3725-3727,
29. Harris, D. C. Quantitative Chemical Analysis, 4th ed.; W. H. Freeman and Co.: New York, 1995; p 352.
30. (a) Metzger, A.; Llynch, V. M.; Anslyn, E. V. Angew. Chem., Int. Ed. 1997, 109, 911-914.
31. (b) Niikura, K.; Metzger, A.; Anslyn, E. V. J. Am. Chem. Soc. 1998, 120, 8533-8534.
32. (c) Wisker, S. L.; Ait-Haddou, H.; Lavigne, J. J.; Anslyn, E. V. Acc. Chem. Res. 2001, 34, 963-972.
33. See the Supporting Information.
34. Perrin, C. L.; Nielson, J. B. Annu. Rev. Phys. Chem. 1997, 48, 511-544.
35. - moieties that we are interested in. The data set obtained was considered of sufficient quality for the purpose of this study. Details are given in the Supporting Information.