A bimetallic helical heptapeptide as a transphosphorylation catalyst in water [7]

Journal of the American Chemical Society

Volumn 121, Issue 29, 1999, Pages 6948-6949

  Rossi, Paola ^a   Felluga, Fulvia ^a   Tecilla, Paolo ^a   Formaggio, Fernando ^b   Crisma, Marco ^b   Toniolo, Claudio ^b   Scrimin, Paolo ^b  

^a UNIVERSITY OF TRIESTE   (Italy)

^b UNIVERSITY OF PADOVA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

HEPTAPEPTIDE; WATER;

CATALYSIS; CATALYST; COMPLEX FORMATION; LETTER; MOLECULAR INTERACTION; PH; PHOSPHORYLATION; REACTION ANALYSIS;

EID: 0033612765     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9908164     Document Type: Letter

References (43)

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31. For dinuclear metal complexes in the cleavage of phosphate esters see: (a) Williams, N. H.; Chin, J. Chem. Commun. 1996, 131; (b) Wahnon, D.; Lebuis, A.-M.; Chin, I. Angew. Chem., Int. Ed. Engl. 1995, 34, 2412. (c) Vance, D. H.; Czarnik, A. W. J. Am. Chem. Soc. 1993, 115, 12165. (d) Chung, Y.; Akkaya, E. U.; Vankatachalam, T. K.; Czarnik, A. W. Tetrahedron Lett. 1990, 31, 5413. (e) Young, M. J.; Chin, J. J. Am. Chem. Soc. 1995, 117, 10577. (f) Wall, M.; Hynes, R. C.; Chin, J. Angew. Chem., Int. Ed. Engl. 1993, 32, 1633. (g) Koike, T.; Inoue, M.; Kimura, E.; Shiro, M. J. Am. Chem. Soc. 1996, 118, 3091. (h) Yashiro, M.; Ishikubo, A.; Komiyama, M. J. Chem. Soc., Chem. Commun. 1995, 1793. (i) Ragunathan, K. G.; Schneider, H.-J. Angew. Chem., Int. Ed. Engl. 1996, 35, 1219. (j) Chapman, W. H. Jr.; Breslow, R. J. Am. Chem. Soc. 1995, 117, 5462.
32. For dinuclear metal complexes in the cleavage of phosphate esters see: (a) Williams, N. H.; Chin, J. Chem. Commun. 1996, 131; (b) Wahnon, D.; Lebuis, A.-M.; Chin, I. Angew. Chem., Int. Ed. Engl. 1995, 34, 2412. (c) Vance, D. H.; Czarnik, A. W. J. Am. Chem. Soc. 1993, 115, 12165. (d) Chung, Y.; Akkaya, E. U.; Vankatachalam, T. K.; Czarnik, A. W. Tetrahedron Lett. 1990, 31, 5413. (e) Young, M. J.; Chin, J. J. Am. Chem. Soc. 1995, 117, 10577. (f) Wall, M.; Hynes, R. C.; Chin, J. Angew. Chem., Int. Ed. Engl. 1993, 32, 1633. (g) Koike, T.; Inoue, M.; Kimura, E.; Shiro, M. J. Am. Chem. Soc. 1996, 118, 3091. (h) Yashiro, M.; Ishikubo, A.; Komiyama, M. J. Chem. Soc., Chem. Commun. 1995, 1793. (i) Ragunathan, K. G.; Schneider, H.-J. Angew. Chem., Int. Ed. Engl. 1996, 35, 1219. (j) Chapman, W. H. Jr.; Breslow, R. J. Am. Chem. Soc. 1995, 117, 5462.
33. For dinuclear metal complexes in the cleavage of phosphate esters see: (a) Williams, N. H.; Chin, J. Chem. Commun. 1996, 131; (b) Wahnon, D.; Lebuis, A.-M.; Chin, I. Angew. Chem., Int. Ed. Engl. 1995, 34, 2412. (c) Vance, D. H.; Czarnik, A. W. J. Am. Chem. Soc. 1993, 115, 12165. (d) Chung, Y.; Akkaya, E. U.; Vankatachalam, T. K.; Czarnik, A. W. Tetrahedron Lett. 1990, 31, 5413. (e) Young, M. J.; Chin, J. J. Am. Chem. Soc. 1995, 117, 10577. (f) Wall, M.; Hynes, R. C.; Chin, J. Angew. Chem., Int. Ed. Engl. 1993, 32, 1633. (g) Koike, T.; Inoue, M.; Kimura, E.; Shiro, M. J. Am. Chem. Soc. 1996, 118, 3091. (h) Yashiro, M.; Ishikubo, A.; Komiyama, M. J. Chem. Soc., Chem. Commun. 1995, 1793. (i) Ragunathan, K. G.; Schneider, H.-J. Angew. Chem., Int. Ed. Engl. 1996, 35, 1219. (j) Chapman, W. H. Jr.; Breslow, R. J. Am. Chem. Soc. 1995, 117, 5462.
34. For dinuclear metal complexes in the cleavage of phosphate esters see: (a) Williams, N. H.; Chin, J. Chem. Commun. 1996, 131; (b) Wahnon, D.; Lebuis, A.-M.; Chin, I. Angew. Chem., Int. Ed. Engl. 1995, 34, 2412. (c) Vance, D. H.; Czarnik, A. W. J. Am. Chem. Soc. 1993, 115, 12165. (d) Chung, Y.; Akkaya, E. U.; Vankatachalam, T. K.; Czarnik, A. W. Tetrahedron Lett. 1990, 31, 5413. (e) Young, M. J.; Chin, J. J. Am. Chem. Soc. 1995, 117, 10577. (f) Wall, M.; Hynes, R. C.; Chin, J. Angew. Chem., Int. Ed. Engl. 1993, 32, 1633. (g) Koike, T.; Inoue, M.; Kimura, E.; Shiro, M. J. Am. Chem. Soc. 1996, 118, 3091. (h) Yashiro, M.; Ishikubo, A.; Komiyama, M. J. Chem. Soc., Chem. Commun. 1995, 1793. (i) Ragunathan, K. G.; Schneider, H.-J. Angew. Chem., Int. Ed. Engl. 1996, 35, 1219. (j) Chapman, W. H. Jr.; Breslow, R. J. Am. Chem. Soc. 1995, 117, 5462.
35. For dinuclear metal complexes in the cleavage of phosphate esters see: (a) Williams, N. H.; Chin, J. Chem. Commun. 1996, 131; (b) Wahnon, D.; Lebuis, A.-M.; Chin, I. Angew. Chem., Int. Ed. Engl. 1995, 34, 2412. (c) Vance, D. H.; Czarnik, A. W. J. Am. Chem. Soc. 1993, 115, 12165. (d) Chung, Y.; Akkaya, E. U.; Vankatachalam, T. K.; Czarnik, A. W. Tetrahedron Lett. 1990, 31, 5413. (e) Young, M. J.; Chin, J. J. Am. Chem. Soc. 1995, 117, 10577. (f) Wall, M.; Hynes, R. C.; Chin, J. Angew. Chem., Int. Ed. Engl. 1993, 32, 1633. (g) Koike, T.; Inoue, M.; Kimura, E.; Shiro, M. J. Am. Chem. Soc. 1996, 118, 3091. (h) Yashiro, M.; Ishikubo, A.; Komiyama, M. J. Chem. Soc., Chem. Commun. 1995, 1793. (i) Ragunathan, K. G.; Schneider, H.-J. Angew. Chem., Int. Ed. Engl. 1996, 35, 1219. (j) Chapman, W. H. Jr.; Breslow, R. J. Am. Chem. Soc. 1995, 117, 5462.
36. For dinuclear metal complexes in the cleavage of phosphate esters see: (a) Williams, N. H.; Chin, J. Chem. Commun. 1996, 131; (b) Wahnon, D.; Lebuis, A.-M.; Chin, I. Angew. Chem., Int. Ed. Engl. 1995, 34, 2412. (c) Vance, D. H.; Czarnik, A. W. J. Am. Chem. Soc. 1993, 115, 12165. (d) Chung, Y.; Akkaya, E. U.; Vankatachalam, T. K.; Czarnik, A. W. Tetrahedron Lett. 1990, 31, 5413. (e) Young, M. J.; Chin, J. J. Am. Chem. Soc. 1995, 117, 10577. (f) Wall, M.; Hynes, R. C.; Chin, J. Angew. Chem., Int. Ed. Engl. 1993, 32, 1633. (g) Koike, T.; Inoue, M.; Kimura, E.; Shiro, M. J. Am. Chem. Soc. 1996, 118, 3091. (h) Yashiro, M.; Ishikubo, A.; Komiyama, M. J. Chem. Soc., Chem. Commun. 1995, 1793. (i) Ragunathan, K. G.; Schneider, H.-J. Angew. Chem., Int. Ed. Engl. 1996, 35, 1219. (j) Chapman, W. H. Jr.; Breslow, R. J. Am. Chem. Soc. 1995, 117, 5462.
37. For dinuclear metal complexes in the cleavage of phosphate esters see: (a) Williams, N. H.; Chin, J. Chem. Commun. 1996, 131; (b) Wahnon, D.; Lebuis, A.-M.; Chin, I. Angew. Chem., Int. Ed. Engl. 1995, 34, 2412. (c) Vance, D. H.; Czarnik, A. W. J. Am. Chem. Soc. 1993, 115, 12165. (d) Chung, Y.; Akkaya, E. U.; Vankatachalam, T. K.; Czarnik, A. W. Tetrahedron Lett. 1990, 31, 5413. (e) Young, M. J.; Chin, J. J. Am. Chem. Soc. 1995, 117, 10577. (f) Wall, M.; Hynes, R. C.; Chin, J. Angew. Chem., Int. Ed. Engl. 1993, 32, 1633. (g) Koike, T.; Inoue, M.; Kimura, E.; Shiro, M. J. Am. Chem. Soc. 1996, 118, 3091. (h) Yashiro, M.; Ishikubo, A.; Komiyama, M. J. Chem. Soc., Chem. Commun. 1995, 1793. (i) Ragunathan, K. G.; Schneider, H.-J. Angew. Chem., Int. Ed. Engl. 1996, 35, 1219. (j) Chapman, W. H. Jr.; Breslow, R. J. Am. Chem. Soc. 1995, 117, 5462.
38. For dinuclear metal complexes in the cleavage of phosphate esters see: (a) Williams, N. H.; Chin, J. Chem. Commun. 1996, 131; (b) Wahnon, D.; Lebuis, A.-M.; Chin, I. Angew. Chem., Int. Ed. Engl. 1995, 34, 2412. (c) Vance, D. H.; Czarnik, A. W. J. Am. Chem. Soc. 1993, 115, 12165. (d) Chung, Y.; Akkaya, E. U.; Vankatachalam, T. K.; Czarnik, A. W. Tetrahedron Lett. 1990, 31, 5413. (e) Young, M. J.; Chin, J. J. Am. Chem. Soc. 1995, 117, 10577. (f) Wall, M.; Hynes, R. C.; Chin, J. Angew. Chem., Int. Ed. Engl. 1993, 32, 1633. (g) Koike, T.; Inoue, M.; Kimura, E.; Shiro, M. J. Am. Chem. Soc. 1996, 118, 3091. (h) Yashiro, M.; Ishikubo, A.; Komiyama, M. J. Chem. Soc., Chem. Commun. 1995, 1793. (i) Ragunathan, K. G.; Schneider, H.-J. Angew. Chem., Int. Ed. Engl. 1996, 35, 1219. (j) Chapman, W. H. Jr.; Breslow, R. J. Am. Chem. Soc. 1995, 117, 5462.
39. For dinuclear metal complexes in the cleavage of phosphate esters see: (a) Williams, N. H.; Chin, J. Chem. Commun. 1996, 131; (b) Wahnon, D.; Lebuis, A.-M.; Chin, I. Angew. Chem., Int. Ed. Engl. 1995, 34, 2412. (c) Vance, D. H.; Czarnik, A. W. J. Am. Chem. Soc. 1993, 115, 12165. (d) Chung, Y.; Akkaya, E. U.; Vankatachalam, T. K.; Czarnik, A. W. Tetrahedron Lett. 1990, 31, 5413. (e) Young, M. J.; Chin, J. J. Am. Chem. Soc. 1995, 117, 10577. (f) Wall, M.; Hynes, R. C.; Chin, J. Angew. Chem., Int. Ed. Engl. 1993, 32, 1633. (g) Koike, T.; Inoue, M.; Kimura, E.; Shiro, M. J. Am. Chem. Soc. 1996, 118, 3091. (h) Yashiro, M.; Ishikubo, A.; Komiyama, M. J. Chem. Soc., Chem. Commun. 1995, 1793. (i) Ragunathan, K. G.; Schneider, H.-J. Angew. Chem., Int. Ed. Engl. 1996, 35, 1219. (j) Chapman, W. H. Jr.; Breslow, R. J. Am. Chem. Soc. 1995, 117, 5462.
40. For a calixarene-based Zn(II) dinuclear catalyst with high binding constant for HPNP, see: Molenveld, P.; Kapsabelis, S.; Engbersen, J. F. J.; Reinhoudt, D. N. J. Am. Chem. Soc. 1997, 119, 2948.
41. For relevant acceleration effects on intramolecular phosphate cleavage by diammonium catalysts see: Dalby, K. N.; Kirby, J. A.; Hollfelder, F. J. Chem. Soc., Perkin Trans. 2 1993, 1269.
42. These experiments also demonstrate that complex 2·2Zn(II) is a real catalyst of the process studied.
43. 16