Applying key concepts from nature: Transition state stabilization, pre-concentration and cooperativity effects in dendritic biomimetics

Progress in Polymer Science (Oxford)

Volumn 30, Issue 3-4, 2005, Pages 385-402

  Liang, Catherine ^a   Fréchet, Jean M J ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Catalyst; Cooperativity; Dendrimer; Enzyme mimic; Molecular pre concentration

Indexed keywords

BIOMIMETIC MATERIALS; CATALYSTS; ENZYMES; MOLECULAR STRUCTURE; MOLECULAR WEIGHT; PH EFFECTS;

COOPERATIVITY; ENZYME MIMIC; MOLECULAR PRE-CONCENTRATION; PLURIMOLECULAR MICELLES;

DENDRIMERS;

EID: 18444373274     PISSN: 00796700     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.progpolymsci.2005.01.004     Document Type: Review

References (75)

1. D. Voet, and G. Voet Judith Biochemistry 1995 Wiley New York p. 332-334
2. J.K.M. Sanders Supramolecular catalysis in transition Chem Eur J 4 8 1998 1378 1383
3. R. Breslow Biomimetic chemistry and artificial enzymes: catalysis by design Acc Chem Res 28 3 1995 146 153
4. V.T. D'Souza Modification of cyclodextrins for use as artificial enzymes Supramol Chem 15 3 2003 221 229
5. T. Habicher, F. Diederich, and V. Gramlich Catalytic dendrophanes as enzyme mimics. Synthesis, binding properties, micropolarity effect, and catalytic activity of dendritic thiazolio-cyclophanes Helv Chim Acta 82 7 1999 1066 1095
6. M. Benaglia, A. Puglisi, and F. Cozzi Polymer-supported organic catalysts Chem Rev 103 9 2003 3401 3429
7. C.W. Wharton Synthetic polymers as models for enzyme catalysis - a review Int J Biol Macromol 1 1 1979 3 16
8. J. Suh Synthesis of polymeric enzyme-like catalysts Synlett 9 2001 1343 1363
9. J. Suh Synthetic artificial peptidases and nucleases using macromolecular catalytic systems Acc Chem Res 36 7 2003 562 570
10. A.S.H. King, and L.J. Twyman Heterogeneous and solid supported dendrimer catalysts J Chem Soc Perkin Trans 1 20 2002 2209 2218
11. C.G. Overberger, and J.C. Salamone Esterolytic action of synthetic macromolecules Acc Chem Res 2 7 1969 217 224
12. C.G. Overberger, T.W. Smith, and K.W. Dixon Catalysis by polymers J Polym Sci Polym Symp 50 1975 1 15
13. C.G. Overberger, A.C. Guterl Jr, Y. Kawakami, L.J. Mathias, A. Meenakshi, and T. Tomono Recent developments in the use of polymers as reactants in organic reactions Pure Appl Chem 50 4 1978 309 313
14. C.G. Overberger, and S. Mitra Catalysis of esterolytic reactions by water-soluble imidazole-containing polymers Pure Appl Chem 51 7 1979 1391 1404
15. J.R. Knowles, and W.J. Albery Perfection in enzyme catalysis: the energetics of triosephosphate isomerase Acc Chem Res 10 4 1977 105 111
16. J.R. Knowles Enzyme catalysis: not different, just better Nature 350 6314 1991 121 124
17. D.A. Tomalia, A.M. Naylor, and W.A. Goddard III Starburst dendrimers: control of size, shape, surface chemistry, topology and flexibility in the conversion of atoms to macroscopic materials Angew Chem 102 2 1990 119 157
18. R. Yin, Y. Zhu, and D.A. Tomalia Architectural copolymers: rod-shaped, cylindrical dendrimers J Am Chem Soc 120 1998 2678 2679
19. D.A. Tomalia, H.M. Brothers II, L.T. Piehler, H.D. Durst, and D.R. Swanson Partial shell-filled core-shell tecto(dendrimers): a strategy to surface differentiated nano-clefts and cusps Proc Natl Acad Sci USA 99 8 2002 5081 5087
20. L.J. Twyman, A.S.H. King, and I.K. Martin Catalysis inside dendrimers Chem Soc Rev 31 2 2002 69 82
21. D. Astruc, and F. Chardac Dendritic catalysts and dendrimers in catalysis Chem Rev 101 9 2001 2991 3023
22. S. Hecht, and J.M.J. Fréchet Dendritic encapsulation of function: applying nature's site isolation principle from biomimetics to materials science Angew Chem Int Ed 40 1 2001 74 91
23. S. Hecht, N. Vladimirov, and J.M.J. Fréchet Encapsulation of functional moieties within branched star polymers: effect of chain length and solvent on site isolation J Am Chem Soc 123 1 2001 18 25
24. E.M. Harth, S. Hecht, B. Helms, E.E. Malmstrom, J.M.J. Fréchet, and C.J. Hawker The effect of macromolecular architecture in nanomaterials: a comparison of site isolation in porphyrin core dendrimers and their isomeric linear analogues J Am Chem Soc 124 15 2002 3926 3938
25. R.M. Crooks, M. Zhao, L. Sun, V. Chechik, and L.K. Yeung Dendrimer-encapsulated metal nanoparticles: synthesis, characterization, and applications to catalysis Acc Chem Res 34 3 2001 181 190
26. H. Brunner Dendrizymes: expanded ligands for enantioselective catalysis J Organomet Chem 500 1-2 1995 39 46
27. B. Ramagnoli, and W. Hayes Chiral dendrimers - from architecturally interesting hyperbranched macromolecules to functional materials J Mater Chem 12 4 2002 767 799
28. H.F. Chow, T.K.K. Mong, C.W. Wan, and Z.Y. Wang Chiral dendrimers Adv Dendr Macromol 4 1999 107 133
29. M.A. Hearshaw, and J.R. Moss Organometallic and related metal-containing dendrimers Chem Commun 1 1999 1 8
30. M.A. Hearshaw, A.T. Hutton, J.R. Moss, and K.J. Naidoo Organometallic dendrimers: synthesis, structural aspects, and applications in catalysis Adv Dendr Macromol 4 1999 1 60
31. R. Kreiter, A.W. Kleij, R.J.M.K. Gebbink, and G. van Koten Dendritic catalysts Top Curr Chem 217 2001 163 199
32. G.E. Oosterom, J.N.H. Reek, P.C.J. Kamer, and P.W.N.M. Van Leeuwen Transition metal catalysis using functionalized dendrimers Angew Chem Int Ed 40 10 2001 1828 1849
33. G. van Koten, and J.T.B.H. Jastrzebski Periphery-functionalized organometallic dendrimers for homogeneous catalysis J Mol Catal A Chem 146 1-2 1999 317 323
34. D. Astruc Organometallic chemistry at the nanoscale. Dendrimers for redox processes and catalysis Pure Appl Chem 75 4 2003 461 481
35. D. Astruc, J.C. Blais, E. Cloutet, L. Djakovitch, S. Rigaut, and J. Ruiz The first organometallic dendrimers: design and redox functions Top Curr Chem 210 2000 229 259
36. J.N.H. Reek, D. De Groot, G.E. Oosterom, P.C.J. Kamer, and P.W.N.M. Van Leeuwen Core and periphery functionalized dendrimers for transition metal catalysis; a covalent and a non-covalent approach Rev Mol Biotech 90 3-4 2002 159 181
37. R. Van Heerbeek, P.C.J. Kamer, P.W.N.M. Van Leeuwen, and J.N.H. Reek Dendrimers as support for recoverable catalysts and reagents Chem Rev 102 10 2002 3717 3756
38. D.K. Smith, and F. Diederich Functional dendrimers: unique biological mimics Chem Eur J 4 8 1998 1353 1361
39. D.K. Smith, and F. Diederich Supramolecular dendrimer chemistry: a journey through the branched architecture Top Curr Chem 210 2000 183 227
40. S. Thayumanavan, P. Bharathi, K. Sivanandan, and D. Rao Vutukuri Towards dendrimers as biomimetic macromolecules CR Chim 6 8-10 2003 767 778
41. Y. Kim, and S.C. Zimmerman Applications of dendrimers in bio-organic chemistry Curr Opin Chem Bio 2 6 1998 733 742
42. A. Zubia, F.P. Cossio, I. Morao, M. Rieumont, and X. Lopez Quantitative evaluation of the catalytic activity of dendrimers with only one active center at the core: application to the nitroaldol (Henry) reaction J Am Chem Soc 126 16 2004 5243 5252
43. M.E. Piotti, F. Rivera, R. Bond, C.J. Hawker, and J.M.J. Fréchet Synthesis and catalytic activity of unimolecular dendritic reverse micelles with 'internal' functional groups J Am Chem Soc 121 40 1999 9471 9472
44. S. Hecht, and J.M.J. Fréchet Light-driven catalysis within dendrimers: designing amphiphilic singlet oxygen sensitizers J Am Chem Soc 123 28 2001 6959 6960
45. I. Morao, and F.P. Cossio Dendritic catalysts for the nitroaldol (Henry) reaction Tetrahedron Lett 38 36 1997 6461 6464
46. A.V. Davis, M. Driffield, and D.K. Smith A dendritic active site: catalysis of the Henry reaction Org Lett 3 20 2001 3075 3078
47. I.K. Martin, and L.J. Twyman Acceleration of an aminolysis reaction using a PAMAM dendrimer with 64 terminal amine groups Tetrahedron Lett 42 6 2001 1123 1126
48. J.L. Burnett, A.S.H. King, I.K. Martin, and L.J. Twyman The effect of size on the rate of an aminolysis reaction using a series of amine terminated PAMAM dendrimers Tetrahedron Lett 43 2002 2431 2433
49. L. Liu, and R. Breslow Dendrimeric pyridoxamine enzyme mimics J Am Chem Soc 125 40 2003 12110 12111
50. W. Zhou, L. Liu, and R. Breslow Transamination by polymeric enzyme mimics Helv Chim Acta 86 11 2003 3560 3567
51. L. Liu, M. Rozenman, and R. Breslow Hydrophobic effects on rates and substrate selectivities in polymeric transaminase mimics J Am Chem Soc 124 43 2002 12660 12661
52. L. Liu, and R. Breslow A potent polymer/pyridoxamine enzyme mimic J Am Chem Soc 124 18 2002 4978 4979
53. C.O. Liang, B. Helms, C.J. Hawker, and J.M.J. Fréchet Dendronized cyclocopolymers with a radial gradient of polarity and their use to catalyze a difficult esterification Chem Commun 20 2003 2524 2525
54. R. Yin, Y. Zhu, and D.A. Tomalia Architectural copolymers: rod-shaped, cylindrical dendrimers J Am Chem Soc 120 1998 2678 2679
55. A.D. Schluter, and J.P. Rabe Dendronized polymers: synthesis, characterization, assembly at interfaces, and manipulation Angew Chem Int Ed Engl 39 5 2000 864 883
56. L. Shu, A.D. Schluter, N. Severin, and J.P. Rabe Extremely long dendronized polymers: synthesis, quantification of structure perfection, individualization, and SFM manipulation Angew Chem Int Ed Engl 40 24 2001 4666 4669
57. H. Ihre, O.L. Padilla de Jesus, and J.M.J. Fréchet Fast and convenient divergent synthesis of aliphatic ester dendrimers by anhydride coupling J Am Chem Soc 123 25 2001 5908 5917
58. S.M. Grayson, and J.M.J. Fréchet Divergent synthesis of dendronized poly(p-hydroxystyrene) Macromolecules 34 19 2001 6542 6544
59. A.W. Bosman, R. Vestberg, A. Heumann, M.J. Fréchet Jean, and C.J. Hawker A modular approach toward functionalized three-dimensional macromolecules: from synthetic concepts to practical applications J Am Chem Soc 125 3 2003 715 728
60. K.Y. Baek, W.R. Dichtel, and J.M.J. Fréchet Synthesis of amphiphilic diblock star polymers with palladium porphyrin cores Polym Prepr 45 1 2004 1008 1009
61. B. Alberts, D. Bray, J. Lewis, M. Raff, K. Roberts, and J.D. Watson Molecular biology of the cell 1994
62. L.A. Baker, and R.M. Crooks Photophysical properties of pyrene-functionalized poly(propylene imine) dendrimers Macromolecules 33 24 2000 9034 9039
63. L.A. Baker, L. Sun, and R.M. Crooks Synthesis and catalytic properties of imidazole-functionalized poly(propylene imine) dendrimers Bull Korean Chem Soc 23 5 2002 647 654
64. C. Francavilla, F.V. Bright, and M.R. Detty Dendrimeric catalysts for the activation of hydrogen peroxide. Increasing activity per catalytic phenylseleno group in successive generations Org Lett 1 7 1999 1043 1046
65. M.R. Detty, C. Francavilla, M.D. Drake, F.V. Bright, and D. Higgs Dendrimeric catalysts for the activation of hydrogen peroxide: improved catalytic activity through statistical effects and cooperativity Polym Mater Sci Eng 84 2001 160 165
66. C. Francavilla, M.D. Drake, F.V. Bright, and M.R. Detty Dendrimeric organochalcogen catalysts for the activation of hydrogen peroxide: improved catalytic activity through statistical effects and cooperativity in successive generations J Am Chem Soc 123 1 2001 57 67
67. R. Breinbauer, and E.N. Jacobsen Cooperative asymmetric catalysis with dendrimeric [Co(salen)] complexes Angew Chem Int Ed 39 20 2000 3604 3607
68. K. Sadler, and J.P. Tam Peptide dendrimers: applications and synthesis Rev Mol Biotech 90 3-4 2002 195 229
69. D. Lagnoux, E. Delort, C. Douat-Casassus, A. Esposito, and J.L. Reymond Synthesis and esterolytic activity of catalytic peptide dendrimers Chem Eur J 10 5 2004 1215 1226
70. A. Esposito, E. Delort, D. Lagnoux, F. Djojo, and J.L. Reymond Catalytic peptide dendrimers Angew Chem Int Ed 42 12 2003 1381 1383
71. A.W. Kleij, R.A. Gossage, J.T.B.H. Jastrzebski, J. Boersma, and G. van Koten The 'dendritic effect' in homogeneous catalysis with carbosilane-supported arylnickel(II) catalysts: observation of active-site proximity effects in atom-transfer radical addition Angew Chem Int Ed 39 1 2000 176 178
72. S.C. Zimmerman, and L.J. Lawless Supramolecular chemistry of dendrimers Top Curr Chem 217 2001 95 120
73. S.C. Zimmerman, M.S. Wendland, N.A. Rakow, I. Zharov, and K.S. Suslick Synthetic hosts by monomolecular imprinting inside dendrimers Nature 418 6896 2002 399 403
74. S.C. Zimmerman, I. Zharov, M.S. Wendland, N.A. Rakow, and K.S. Suslick Molecular imprinting inside dendrimers J Am Chem Soc 125 44 2003 13504 13518
75. E. Mertz, and S.C. Zimmerman Cross-linked dendrimer hosts containing reporter groups for amine guests J Am Chem Soc 125 12 2003 3424 3425