Synthesis and reactivity of a C3-symmetric trinuclear zinc(ii) hydroxide catalyst efficient at phosphate diester transesterification

Dalton Transactions

Volumn , Issue 35, 2007, Pages 3924-3935

  Mitra, Ranjan ^a   Peters, Matthew W ^a   Scott, Michael J ^a  

^a University of Florida ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON INORGANIC COMPOUNDS; CATALYSTS; CYCLIZATION; ENZYMES; HYDROLYSIS; LIGANDS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHOSPHATES; POTENTIOMETERS (ELECTRIC MEASURING INSTRUMENTS); RNA; SYNTHESIS (CHEMICAL); X RAY CRYSTALLOGRAPHY;

HYDROXIDE; INTRAMOLECULAR INTERACTION; MOIETIES; MONONUCLEAR ANALOGUE; PHOSPHATE DIESTER TRANSESTERIFICATION; TRINUCLEAR ZN;

ZINC COMPOUNDS;

2 (HYDROXYPROPYL) 4 NITROPHENYL PHOSPHATE; 2-(HYDROXYPROPYL)-4-NITROPHENYL PHOSPHATE; ESTER; HYDROXIDE; LIGAND; ORGANOMETALLIC COMPOUND; ORGANOPHOSPHORUS COMPOUND; PHOSPHATE; PROTON; RNA; WATER; ZINC;

ARTICLE; CATALYSIS; CHEMISTRY; ESTERIFICATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PH; SOLUTION AND SOLUBILITY; SYNTHESIS; TEMPERATURE;

CATALYSIS; ESTERIFICATION; ESTERS; HYDROGEN-ION CONCENTRATION; HYDROXIDES; LIGANDS; MAGNETIC RESONANCE SPECTROSCOPY; ORGANOMETALLIC COMPOUNDS; ORGANOPHOSPHORUS COMPOUNDS; PHOSPHATES; PROTONS; RNA; SOLUTIONS; TEMPERATURE; WATER; ZINC;

EID: 34648829855     PISSN: 14779226     EISSN: 14779234     Source Type: Journal    
DOI: 10.1039/b706386e     Document Type: Article

References (86)

1. F. H. Westheimer Science 1987 235 1173
2. N. H. Williams B. Takasaki M. Wall J. Chin Acc. Chem. Res. 1999 32 485
3. N. Strater W. N. Lipscomb T. Klabunde B. Krebs Angew. Chem., Int. Ed. Engl. 1996 35 2024
4. D. E. Wilcox Chem. Rev. 1996 96 2435
5. J. A. Cowan Chem. Rev. 1998 98 1067
6. M. J. Jedrzejas P. Setlow Chem. Rev. 2001 101 607
7. M. M. Benning H. Shim F. M. Raushel H. M. Holden Biochemistry 2001 40 2712
8. H. Shim F. M. Raushel Biochemistry 2000 39 7357
9. E. E. Kim H. W. Wyckoff J. Mol. Biol. 1991 218 449
10. B. Stec K. M. Holtz E. R. Kantrowitz J. Mol. Biol. 2000 299 1303
11. S. Hansen L. K. Hansen E. Hough J. Mol. Biol. 1993 231 870
12. S. Hansen L. Kristian H. Hough E. Hough J. Mol. Biol. 1992 225 543
13. E. Hough L. K. Hansen B. Birknes K. Jynge S. Hansen A. Hordvik C. Little E. Dodson Z. Derewenda Nature 1989 338 357
14. C. Romier R. Dominguez A. Lahm O. Dahl D. Suck Proteins 1998 32 414
15. A. Volbeda A. Lahm F. Sakiyama D. Suck EMBO J. 1991 10 1607
16. C. G. Zhan F. Zheng J. Am. Chem. Soc. 2001 123 2835
17. Z. G. Wang W. Fast S. J. Benkovic Biochemistry 1999 38 10013
18. E. L. Hegg J. N. Burstyn Coord. Chem. Rev. 1998 173 133
19. J. Weston Chem. Rev. 2005 105 2151
20. G. Parkin Chem. Rev. 2004 104 699
21. J. R. Morrow O. Iranzo Curr. Opin. Chem. Biol. 2004 8 192
22. E. Kimura Curr. Opin. Chem. Biol. 2000 4 207
23. P. Molenveld J. F. J. Engbersen D. N. Reinhoudt Chem. Soc. Rev. 2000 29 75
24. M. Komiyama J. Sumaoka Curr. Opin. Chem. Biol. 1998 2 751
25. R. Breslow Acc. Chem. Res. 1995 28 146
26. P. Molenveld W. M. G. Stikvoort H. Kooijman A. L. Spek J. F. J. Engbersen D. N. Reinhoudt J. Org. Chem. 1999 64 3896
27. P. Molenveld S. Kapsabelis J. F. J. Engbersen D. N. Reinhoudt J. Am. Chem. Soc. 1997 119 2948
28. P. Molenveld J. F. J. Engbersen D. N. Reinhoudt Eur. J. Org. Chem. 1999 3269
29. O. Iranzo A. Y. Kovalevsky J. R. Morrow J. P. Richard J. Am. Chem. Soc. 2003 125 1988
30. K. P. McCue J. R. Morrow Inorg. Chem. 1999 38 6136
31. T. Gajda R. Kramer A. Jancso Eur. J. Inorg. Chem. 2000 1635
32. M. Yashiro A. Ishikubo M. Komiyama J. Chem. Soc., Chem. Commun. 1995 1793
33. P. Rossi F. Felluga P. Tecilla F. Formaggio M. Crisma C. Toniolo P. Scrimin J. Am. Chem. Soc. 1999 121 6948
34. P. Rossi F. Felluga P. Tecilla F. Formaggio M. Crisma C. Toniolo P. Scrimin Biopolymers 2000 55 496
35. C. Sissi P. Rossi F. Felluga F. Formaggio M. Palumbo P. Tecilla C. Toniolo P. Scrimin J. Am. Chem. Soc. 2001 123 3169
36. A. Scarso U. Scheffer M. Gobel Q. B. Broxterman B. Kaptein F. Formaggio C. Toniolo P. Scrimin Proc. Natl. Acad. Sci. USA 2002 99 5144
37. N. V. Kaminskaia C. He S. J. Lippard Inorg. Chem. 2000 39 3365
38. C. He S. J. Lippard J. Am. Chem. Soc. 2000 122 184
39. A. M. Barrios S. J. Lippard Inorg. Chem. 2001 40 1060
40. B. Bauer-Siebenlist F. Meyer E. Farkas D. Vidovic J. A. Cuesta-Seijo R. Herbst-Irmer H. Pritzkow Inorg. Chem. 2004 43 4189
41. F. Meyer P. Rutsch Chem. Commun. 1998 1037
42. C. Bazzicalupi A. Bencini A. Bianchi V. Fusi L. Mazzanti P. Paoletti B. Valtancoli Inorg. Chem. 1995 34 3003
43. C. Bazzicalupi A. Bencini A. Bianchi V. Fusi P. Paoletti B. Valtancoli J. Chem. Soc., Chem. Commun. 1994 881
44. C. Bazzicalupi A. Bencini A. Bianchi F. Corana V. Fusi C. Giorgi P. Paoli P. Paoletti B. Valtancoli C. Zanchini Inorg. Chem. 1996 35 5540
45. C. Bazzicalupi A. Bencini A. Bianchi V. Fusi P. Paoletti B. Valtancoli J. Chem. Soc., Chem. Commun. 1995 1555
46. C. Bazzicalupi A. Bencini A. Bianchi V. Fusi P. Paoletti G. Piccardi B. Valtancoli Inorg. Chem. 1995 34 5622
47. C. Bazzicalupi A. Bencini A. Bianchi V. Fusi C. Giorgi P. Paoletti B. Valtancoli D. Zanchi Inorg. Chem. 1997 36 2784
48. A. Bencini E. Berni A. Bianchi C. Giorgi B. Valtancoli Supramol. Chem. 2001 13 489
49. A. Bencini E. Berni A. Bianchi V. Fedi C. Giorgi P. Paoletti B. Valtancoli Inorg. Chem. 1999 38 6323
50. C. Bazzicalupi A. Bencini E. Berni A. Bianchi V. Fedi V. Fusi C. Giorgi P. Paoletti B. Valtancoli Inorg. Chem. 1999 38 4115
51. M. Yashiro A. Ishikubo M. Komiyama Chem. Commun. 1997 83
52. C. Bazzicalupi A. Bencini E. Berni C. Giorgi S. Maoggi B. Valtancoli Dalton Trans. 2003 3574
53. S. R. Korupoju N. Mangayarkarasi P. S. Zacharias J. Mizuthani H. Nishihara Inorg. Chem. 2002 41 4099
54. M. B. Dinger M. J. Scott Eur. J. Org. Chem. 2000 2467
55. M. J. Plater M. R. S. Foreman T. Gelbrich M. B. Hursthouse J. Chem. Soc., Dalton Trans. 2000 1995
56. S. Uhlenbrock R. Wegner B. Krebs J. Chem. Soc., Dalton Trans. 1996 3731
57. A. Looney R. Han I. B. Gorrell M. Cornebise K. Yoon G. Parkin A. L. Rheingold Organometallics 1995 14 274
58. J. C. M. Rivas E. Salvagni R. T. M. de Rosales S. Parsons Dalton Trans. 2003 3339
59. E. Kinoshita M. Takahashi H. Takeda M. Shiro T. Koike Dalton Trans. 2004 1189
60. H. B. Collier Clin. Chem. 1979 25 495
61. J. E. Huheey, in Inorganic Chemistry, Harper, Cambridge, 1983, 3rd edn, p. 150
62. C. Bleiholder H. Borzel P. Comba R. Ferrari M. Heydt M. Kerscher S. Kuwata G. Laurenczy G. A. Lawrance A. Lienke B. Martin M. Merz B. Nuber H. Pritzkow Inorg. Chem. 2005 44 8145
63. A. E. Martell and R. J. Motekaitis, Determination and Use of Stability Constants, VCH, New York, 1992, 2nd edn
64. A. E. Martell and R. M. Smith, Critical Stability Constants, Plenum Press, New York, 1982
65. S. H. Gellman R. Petter R. Breslow J. Am. Chem. Soc. 1986 108 2388
66. P. Molenveld J. F. J. Engbersen D. N. Reinhoudt Angew. Chem., Int. Ed. 1999 38 3189
67. W. N. Lipscomb N. Strater Chem. Rev. 1996 96 2375
68. B. Bennett R. C. Holz J. Am. Chem. Soc. 1997 119 1923
69. X. D. Wang R. Y. N. Ho A. K. Whiting L. Que J. Am. Chem. Soc. 1999 121 9235
70. T. Gajda A. Jancso S. Mikkola H. Lonnberg H. Sirges J. Chem. Soc., Dalton Trans. 2002 1757
71. C. Bazzicalupi A. Bencini E. Berni A. Bianchi P. Fornasari C. Giorgi B. Valtancoli Inorg. Chem. 2004 43 6255
72. P. Gettins J. E. Coleman J. Biol. Chem. 1984 259 4991
73. L. Ma T. T. Tibbitts E. R. Kantrowitz Protein Sci. 1995 4 1498
74. F. Hollfelder D. Herschlag Biochemistry 1995 34 12255
75. J. E. Murphy T. T. Tibbitts E. R. Kantrowitz J. Mol. Biol. 1995 253 604
76. S. Hansen E. Hough L. A. Svensson Y. L. Wong S. F. Martin J. Mol. Biol. 1993 234 179
77. S. F. Martin Y. L. Wong A. S. Wagman J. Org. Chem. 1994 59 4821
78. L. Bonfa M. Gatos F. Mancin P. Tecilla U. Toneliato Inorg. Chem. 2003 42 3943
79. D. M. Brown D. A. Usher J. Chem. Soc. 1965 6558
80. E. Carceller M. Merlos M. Giral C. Almansa J. Bartroli J. Garciarafanell J. Forn J. Med. Chem. 1993 36 2984
81. M. B. Dinger M. J. Scott Inorg. Chem. 2001 40 856
82. R. H. Blessing Acta Crystallogr., Sect. A 1995 A51 33
83. J. Bassett, R. C. Denney, G. H. Jeffery and J. Mendham, in Titrimetric Analysis, John Wiley & Sons, New York, 1978
84. C. F. Bernasconi W. T. Sun J. Am. Chem. Soc. 1993 115 12526
85. G. Gran Analyst 1952 77 661
86. F. J. Rossotti H. Rossotti J. Chem. Educ. 1965 42 375