Polyethylene imine derivatives ('synzymes') accelerate phosphate transfer in the absence of metal

Journal of the American Chemical Society

Volumn 129, Issue 24, 2007, Pages 7611-7619

  Avenier, Frédéric ^a   Domingos, Josiel B ^a,b   Van Vliet, Liisa D ^a   Hollfelder, Florian ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

^b FEDERAL UNIVERSITY OF SANTA CATARINA   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

INTRAMOLECULAR TRANSESTERIFICATION; PHOSPHATE TRANSFER; POLYETHYLENE IMINE (PEI); SYNZYMES;

AMINES; CATALYSIS; DERIVATIVES; GROUND STATE; MOLECULAR RECOGNITION; SUBSTRATES;

POLYETHYLENES;

2 HYDROXYPROPYL 3 NITROPHENYL PHOSPHATE; ALKYL GROUP; BENZYL DERIVATIVE; GUANIDINE; HYDROXIDE; PHOSPHATE; POLYETHYLENEIMINE; POLYMER; SMALL MOLECULE TRANSPORT AGENT; UNCLASSIFIED DRUG;

ACCELERATION; ARTICLE; CATALYSIS; CHEMICAL BINDING; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; DERIVATIZATION; HYDROPHOBICITY; MOLECULAR RECOGNITION; PH; PHOSPHATE TRANSPORT; PROTON TRANSPORT; TRANSESTERIFICATION;

CATALYSIS; ENZYMES; HYDROGEN-ION CONCENTRATION; IMINES; METALS; MODELS, CHEMICAL; MOLECULAR STRUCTURE; PHOSPHATES; POLYETHYLENES;

EID: 34250832691     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja069095g     Document Type: Article

References (62)

1. Cleland, W. W.; Hengge, A. C. Chem. Rev. 2006, 106, 3252-78.
2. Cowan, J. A. Chem. Rev. 1998, 98 (3), 1067-1088.
3. Steitz, T. A.; Steitz, J. A. Proc. Natl. Acad. Sci. U.S.A 1993, 90 (14), 6498-502.
4. Wilcox, D. E. Chem. Rev. 1996, 96 (7), 2435-2458.
5. Raines, R. T. Chem. Rev. 1998, 98 (3), 1045-1066.
6. Morrow, J. R.; Iranzo, O. Curr. Opin. Chem. Biol. 2004, 8 (2), 192-200.
7. Molenveld, P.; Engbersen, J. F. J.; Reinhoudt, D. N. Chem. Soc. Rev. 2000, 29, 75-86.
8. Williams, N. H.; Takasaki, B.; Wall, M.; Chin, J. Acc. Chem. Res. 1999, 32, 485-493.
9. Anslyn, E.; Breslow, R. J. Am. Chem. Soc. 1989, 111, 5972-5973.
10. Jubian, V.; Veronese, A.; Dixon, R. P.; Hamilton, A. D. Angew. Chem., Int. Ed. Engl. 1995, 34 (11), 1237-1239.
11. Krai, V.; Lang, K.; Kralova, J.; Dvorak, M.; Martasek, P.; Chin, A. O.; Andrievsky, A.; Lynch, V.; Sessler, J. L. J. Am. Chem. Soc. 2006, 128 (2), 432-437.
12. Scheffer, U.; Strick, A.; Ludwig, V.; Peter, S.; Kalden, E.; Göbel, M. W. J. Am. Chem. Soc. 2005, 127 (7), 2211-7.
13. Piatek, A. M.; Gray, M.; Anslyn, E. V. J. Am. Chem. Soc. 2004, 126 (32), 9878-9.
14. Kofoed, J.; Reymond, J. L. Curr. Opin. Chem. Biol. 2005, 9 (6), 656-64.
15. Klotz, I. In Enzyme Mechanisms; Page, M. I., Williams, A., Eds.; The Royal Society of Chemistry: London, 1987; pp 14-34.
16. Klotz, I. M.; Suh, J. In Artificial Enzymes; Breslow, R., Ed.; Wiley-VCH: Weinheim, 2005; pp 63-88.
17. Suh, J. Synlett 2001, 9, 1343-1363.
18. Liu, L.; Zhou, W.; Chruma, J.; Breslow, R. J. Am. Chem. Soc. 2004, 126 (26), 8136-7.
19. Liu, L.; Breslow, R. J. Am. Chem. Soc. 2002, 124 (18), 4978-9.
20. Liu, L.; Breslow, R. Bioorg. Med. Chem. 2004, 12 (12), 3277-87.
21. Liu, L.; Rozenman, M.; Breslow, R. J. Am. Chem. Soc. 2002, 124 (43), 12660-1.
22. Breslow, R.; Bandyopadhyay, S.; Levine, M.; Zhou, W. Chembiochem 2006, 7 (10), 1491-6.
23. Haimov, A.; Cohen, H.; Neumann, R. J. Am. Chem. Soc. 2004, 126 (38), 11762-3.
24. Casey, L. M.; Kemp, D. S.; Paul, K. G.; Cox, D. D. J. Org. Chem. 1973, 38 (13), 2294-2301.
25. Kemp, D. S.; Casey, M. L. J. Am. Chem. Soc. 1973, 95, 6670-6680.
26. Kemp, D. S.; Cox, D. D.; Paul, K. G. J. Am. Chem. Soc. 1975, 7312-7318.
27. Kemp, D. S.; Paul, K. G. J. Am. Chem. Soc. 1975, 7305-7312.
28. Hollfelder, F.; Kirby, A. J.; Tawfik, D. S. J. Am. Chem. Soc. 1997, 119, 9578-9579.
29. Hollfelder, F.; Kirby, A. J.; Tawfik, D. S. J. Org. Chem. 2001, 66 (17), 5866-74.
30. Brown, D. M.; Usher, D. A. J. Chem. Soc. 1965, 6558-6564.
31. Perreault, D. M.; Cabell, L. A.; Anslyn, E. V. Bioorg. Med. Chem. 1997, 5 (6), 1209-20.
32. Schug, K. A.; Lindner, W. Chem. Rev. 2005, 105 (1), 67-114.
33. Bernatowicz, M. S.; Wu, Y.; Matsueda, G. R. J. Org. Chem. 1992, 57, 2497-2502.
34. Yakovlev, G. I.; Mitkevich, V. A.; Shaw, K. L.; Trevino, S.; Newsom, S.; Pace, C. N.; Makarov, A. A. Protein Sci. 2003, 12 (10), 2367-73.
35. Yakovlev, G. I.; Struminskaya, N. K.; Znamenskaya, L. V.; Kipenskaya, L. V.; Leschinskaya, I. B.; Hartley, R. W. FEBS Lett. 1998, 428 (1-2), 57-8.
36. Cotton, F. A.; Hazen, E. E., Jr.; Legg, M. J. Proc. Natl. Acad. Sci. U.S.A. 1979, 76 (6), 2551-5.
37. Serpersu, E. H.; Shortle, D.; Mildvan, A. S. Biochemistry 1987, 26 (5), 1289-300.
38. Coleman, J. E. Annu. Rev. Biophys. Biomol. Struct. 1992, 21, 441-83.
39. Neverov, A. A.; Lu, Z. L.; Maxwell, C. I.; Mohamed, M. F.; White, C. J.; Tsang, J. S.; Brown, R. S. J. Am. Chem. Soc. 2006, 128 (50), 16398-405.
40. Avenier, F.; Hollfelder, F. Unpublished observations.
41. Spetnagel, W. J.; Klotz, I. M. J. Am. Chem. Soc. 1976, 98 8199-8204.
42. Suh, J.; Scarpa, I. S.; Klotz, I. M. J. Am. Chem. Soc. 1976, 98, 7060-7064.
43. Molenveld, P.; Stikvoort, W. M. G.; Kooijman, H.; Spek, A. L.; Engbersen, J. F. J.; Reinhoudt, D. N. J. Org. Chem. 1999, 64, 3896-3906.
44. Manea, F.; Houillon, F. B.; Pasquato, L.; Scrimin, P. Angew. Chem., Int. Ed. Engl. 2004, 43 (45), 6165-9.
45. Suh, J.; Hong, S. H. J. Am. Chem. Soc. 1998, 120, 12545-12552.
46. Iranzo, O.; Kovalevsky, A. Y.; Morrow, J. R.; Richard, J. P. J. Am. Chem. Soc. 2003, 125 (7), 1988-93.
47. Feng, G.; Natale, D.; Prabaharan, R.; Mareque-Rivas, J. C.; Williams, N. H. Angew. Chem., Int. Ed. Engl. 2006, 45 (42), 7056-9.
48. Kovari, E.; Kramer, R. J. Am. Chem. Soc. 1996, 118, 12704-12709.
49. Breslow, R.; Schmuck, C. J. Am. Chem. Soc. 1996, 118, 6601-6605.
50. Wolfenden, R. Chem. Rev. 2006, 106, (8), 3379-96.
51. Feng, G.; Mareque-Rivas, J. C.; Torres Martin de Rosales, R.; Williams, N. H. J. Am. Chem. Soc. 2005, 127 (39), 13470-1.
52. 50 increase from 0.15 μM at pH 7 to 0.25 μM at pH 8 (see Supporting Information, Figure S3) reflecting the decreasing positive charge of the polymer. However, inhibition by naphthyl phosphate is independent of pH, highlighting that for this inhibitor pH-independent hydrophobic effects predominate over ionic effects.
53. Sarpal, R. S.; Dogra, S. K. J. Chem. Soc., Faraday Trans. 1992, 88 (18), 2725-2731.
54. Hauser, S. L.; Johanson, E. W.; Green, H. P.; Smith, P. J. Org. Lett. 2000, 2 (23), 3575-8.
55. Cox, J. R.; Ramsey, O. B. Chem. Rev. 1964, 64, 317-351.
56. Abell, K. W. Y.; Kirby, A. J. Tetrahedron Lett. 1986, 27 (9), 1085-1088.
57. Kirby, A. J. Angew. Chem., Int. Ed. Engl. 1996, 35, 707-724.
58. Hunter, C. A. Angew. Chem., Int. Ed. Engl. 2004, 43 (40), 5310-24.
59. -1).
60. uncat.
61. uncat/1 M (assuming 1 M catalyst).
62. Oost, T.; Filippazzi, A.; Kalesse, M. Liebigs Ann. Chem. 1997, 1005-1011.