The role of dynamically correlated conformational equilibria in the folding of macromolecular structures. A model for the design of folded dendrimers

Progress in Polymer Science (Oxford)

Volumn 30, Issue 3-4, 2005, Pages 423-452

  Lockman, Jeffrey W ^a   Paul, Noel M ^a   Parquette, Jon R ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

Correlated conformational fluctuations; Dendrimers; Folding; Macromolecules; Proteins; Supramolecular assemblies

Indexed keywords

CONFORMATIONS; ENTROPY; MACROMOLECULES; MATHEMATICAL MODELS; PERTURBATION TECHNIQUES; THERMODYNAMIC STABILITY;

CORRELATED CONFORMATIONAL FLUCTUATIONS; FOLDING; LIGAND BINDING; SUPRAMOLECULAR ASSEMBLIES;

DENDRIMERS;

EID: 18444369978     PISSN: 00796700     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.progpolymsci.2005.01.012     Document Type: Review

References (183)

1. T.E. Creighton Proteins: structures and molecular properties 2nd ed 1993 W.H. Freeman New York
2. For excellent reviews, see: (a) D.J. Hill, M.J. Mio, R.B. Prince, T.S. Hughes, and J.S. Moore A field guide to foldamers Chem Rev 101 2001 3893
3. R.P. Cheng, S.H. Gellman, and W.F. DeGrado β-Peptides: from structure to function Chem Rev 101 2001 3219
4. S.H. Gellman Foldamers: a manifesto Acc Chem Res 31 1998 173 180
5. J.R. Parquette The intramolecular self-organization of dendrimers Comptes Rendus Chimie 6 2003 779 789
6. C.L. Brooks III, M. Gruebele, J.N. Onuchic, and P.G. Wolynes Chemical physics of protein folding Proc Natl Acad Sci USA 95 1998 11037 11038
7. O. Jardetzky Protein dynamics and conformational transitions in allosteric proteins Prog Biophys Mol Biol 65 1997 171 219
8. D. Kern, and E.R.P. Zuiderweg The role of dynamics in allosteric regulation Curr Opin Struct Biol 13 2003 748 757
9. J.M. Yon, D. Perahia, and C. Ghelis Conformational dynamics and enzyme activity Biochimie 80 1998 33 42
10. M.J. Stone NMR relaxation studies of the role of conformational entropy in protein stability and ligand binding Acc Chem Res 34 2001 379 388
11. K.L. Mayer, M.R. Earley, S. Gupta, K. Pichumani, L. Regan, and M.J. Stone Covariation of backbone motion throughout a small protein domain Nat Struct Biol 10 2003 962 965
12. R.V. Pappu, R. Srinivasan, and G.D. Rose The Flory isolated-pair hypothesis is not valid for polypeptide chains: implications for protein folding Proc Natl Acad Sci USA 97 2000 12565
13. A.J. Wand Dynamic activation of protein function: a view emerging from NMR spectroscopy Nat Struct Biol 8 2001 926 931
14. M.J. Stone, S. Gupta, N. Snyder, and L. Regan Comparison of protein backbone entropy and β-sheet stability: NMR-derived dynamics of protein G B1 domain mutants J Am Chem Soc 123 2001 185 186
15. M.J. Seewald, K. Pichumani, C. Stowell, B.V. Tibbals, L. Regan, and M.J. Stone The role of backbone conformational heat capacity in protein stability: temperature dependent dynamics of the B1 domain of streptococcal protein G Protein Sci 9 6 2000 1177 1193
16. I. Luque, S.A. Leavitt, and E. Freire The linkage between protein folding and functional cooperativity: two sides of the same coin? Annu Rev Biophys Biomol Struct 31 2002 235 256
17. H. Pan, J.C. Lee, and V.J. Hilser Binding sites in Escherichia coli dihydrofolate reductase communicate by modulating the conformational ensemble Proc Natl Acad Sci USA 97 2000 12020 12025
18. 2+-binding protein calbindin D9k Nat Struct Biol 7 2000 245 250
19. T. Nakano, and Y. Okamoto Synthetic helical polymers: conformation and function Chem Rev 101 2001 4013 4038
20. Y. Okamoto, and T. Nakano Asymmetric polymerization Chem Rev 94 1994 349 372
21. L.S. Corley, and O. Vogl Haloaldehyde polymers XXI. Optically active polychloral Polym Bull 3 1980 211 217
22. K. Ute, K. Hirose, H. Kashimoto, H. Nakayama, K. Hatada, and O. Vogl Helix-inversion equilibrium of isotactic chloral oligomers in solution Polym Bull 25 1993 1175 1186
23. M. Ishikawa, K. Maeda, Y. Mitsutsuji, and E. Yashima An unprecedented memory of macromolecular helicity induced in an achiral polyisocyanide in water J Am Chem Soc 126 2004 732 733
24. Y. Ito, T. Miyake, S. Hatano, R. Shima, T. Ohara, and M. Suginome Asymmetric synthesis of helical poly(quinoxaline-2,3-diyl)s by palladium-mediated polymerization of 1,2-diisocyanobenzenes: effective control of the screw-sense by a binaphthyl group at the chain-end J Am Chem Soc 120 1998 11880 11893
25. E. Yashima, K. Maeda, and T. Nishimura Detection and amplification of chirality by helical polymers Chem Eur J 10 2004 42 51
26. M.M. Green, J.-W. Park, T. Sato, A. Teramoto, S. Lifson, and R.L.B. Selinger The macromolecular route to chiral amplification Angew Chem Int Ed Eng 38 1999 3139 3154
27. S. Mayer, and R. Zentel Chiral polyisocyanates, a special class of helical polymers Prog Polym Sci 26 2001 1973 2013
28. M.M. Green, N.C. Peterson, T. Sato, A. Teramoto, R. Cook, and S. Lifson A helical polymer with a cooperative response to chiral information Science 268 1995 1860 1866
29. S. Lifson, C.E. Felder, and M.M. Green Helical conformations, internal motion, and helix sense reversal in polyisocyanates and the preferred helix sense of an optically active polyisocyanate Macromolecules 25 1992 4142 4148
30. K. Ute, Y. Fukunishi, S.K. Jha, K.-S. Cheon, B. Munoz, and K. Hatada Dynamic NMR determination of the barrier for interconversion of the left- and right-handed helical conformations in a polyisocyanate Macromolecules 32 1999 1304 1307
31. M.M. Green, B.A. Garetz, B. Munoz, H. Chang, S. Hoke, and R.G. Cooks Majority rules in the copolymerization of mirror image isomers J Am Chem Soc 117 1995 4181 4182
32. H. Gu, Y. Nakamura, T. Sato, A. Teramoto, M.M. Green, and C. Andreola Molecular-weight dependence of the optical rotation of poly((R)-2-deuterio-n- hexyl isocyanate) Macromolecules 28 1995 1016 1024
33. M.M. Green, C. Andreola, B. Munoz, M.P. Reidy, and K. Zero Macromolecular stereochemistry: a cooperative deuterium isotope effect leading to a large optical rotation J Am Chem Soc 110 1988 4063 4065
34. For a review, see: (a) A. Teramoto Cooperative conformational transitions in linear macromolecules undergoing chiral perturbations Prog Polym Sci 26 2001 667 720
35. H. Gu, Y. Nakamura, T. Sato, A. Teramoto, M.M. Green, and C. Andreola Molecular-weight dependence of the optical rotation of poly((R)-2-deuterio-n- hexyl isocyanate) Macromolecules 28 1995 1016 1024
36. M.M. Green, M.P. Reidy, R.J. Johnson, G. Darling, D.J. Oleary, and G. Willson Macromolecular stereochemistry - the out-of-proportion influence of optically-active co-monomers on the conformational characteristics of polyisocyanates - the sergeants and soldiers experiment J Am Chem Soc 111 1989 6452 6454
37. M.M. Green, B.A. Garetz, B. Munoz, H. Chang, S. Hoke, and R.G. Cooks Majority rules in the copolymerization of mirror image isomers J Am Chem Soc 117 1995 4181 4182
38. For some examples of cooperativity in polyisocyanate polymers, see: M.M. Green, B.A. Garetz, B. Munoz, H. Chang, S. Hoke, and R.G. Cooks Majority rules in the copolymerization of mirror image isomers J Am Chem Soc 117 1995 4181 4182
39. M.M. Green, N.C. Peterson, T. Sato, A. Teramoto, R. Cook, and S. Lifson A helical polymer with a cooperative response to chiral information Science 268 1995 1860 1866
40. M.M. Green, M.P. Reidy, R.D. Johnson, G. Darling, D.J. O'Leary, and G. Willson Macromolecular stereochemistry: the out-of-proportion influence of optically active comonomers on the conformational characteristics of polyisocyanates. The sergeants and soldiers experiment J Am Chem Soc 111 1989 6452 6454
41. H. Gu, Y. Nakamura, T. Sato, A. Teramoto, M.M. Green, and S.K. Jha Optical rotation of random copolyisocyanates of chiral and achiral monomers: sergeant and soldier copolymers Macromolecules 31 1998 6362 6368
42. S. Mayer, G. Maxein, and R. Zentel Correlation between the isomerization of side groups and the helical main chain in chiral polyisocyanates Macromolecules 31 1998 8522 8525
43. A. Saxena, G. Guo, M. Fujiki, Y. Yang, A. Ohira, and K. Okoshi Helical polymer command surface: thermodriven chiroptical transfer and amplification in binary polysilane film system Macromolecules 37 9 2004 3081 3083
44. M. Fujiki, H. Nakashima, S. Toyoda, and J.R. Koe Chirality in the polysilanes Top Stereochem 24 2003 209 280
45. G. Gao, F. Sanda, and T. Masuda Copolymerization of chiral amino acid-based acetylenes and helical conformation of the copolymers Macromolecules 36 2003 3938 3943
46. R. Nonokawa, and E. Yashima Detection and amplification of a small enantiomeric imbalance in a-amino acids by a helical poly(phenylacetylene) with crown ether pendants J Am Chem Soc 125 2003 1278 1283
47. H. Nakako, R. Nomura, and T. Masuda Helix inversion of poly(propiolic esters) Macromolecules 34 2001 1496 1502
48. B.M.W. Langeveld-Voss, R.J.M. Waterval, R.A.J. Janssen, and E.W. Meijer Principles of 'majority rules' and 'sergeants and soldiers' applied to the aggregation of optically active polythiophenes: evidence for a multichain phenomenon Macromolecules 32 1999 227 230
49. A.P.H.J. Schenning, A.F.M. Kilbinger, F. Biscarini, M. Cavallini, H.J. Cooper, and P.J. Derrick Supramolecular organization of α,α′- disubstituted sexithiophenes J Am Chem Soc 124 2002 1269 1275
50. E. Yashima, K. Maeda, and T. Yamanaka Helicity induction and conformational dynamics of poly(bis(4-carboxyphenoxy)phosphazene) with optically active amines J Am Chem Soc 122 2000 7813 7814
51. M.R. Majidi, L.A.P. Kane-Maguire, and G.G. Wallace Chemical generation of optically active polyaniline via the doping of emeraldine base with (+)- or (-)-camphorsulfonic acid Polymer 36 1995 3597 3599
52. Y. Zhou, B. Yu, and G. Zhu Electropolymeric generation of optically active polypyrrole Polymer 38 1997 5493 5495
53. R.B. Prince, J.S. Moore, L. Brunsveld, and E.W. Meijer Cooperativity in the folding of helical m-phenylene ethynylene oligomers based upon the 'sergeants-and-soldiers' principle Chem Eur J 7 2001 4150 4154
54. M.S. Gin, T. Yokozawa, R.B. Prince, and J.S. Moore Helical bias in solvophobically folded oligo(phenylene ethynylene)s J Am Chem Soc 121 1999 2643 2644
55. J.H.K.K. Hirschberg, R.A. Koevoets, R.P. Sijbesma, and E.W. Meijer Helical supramolecular aggregates based on ureidopyrimidinone quadruple hydrogen bonding Chem Eur J 9 2003 4222 4231
56. A. Natansohn, and P. Rochon Photoinduced motions in azo-containing polymers Chem Rev 102 2002 4139 4175
57. H.-Z. Tang, Y. Lu, G. Tian, M.D. Capracotta, and B.M. Novak Stable helical polyguanidines: poly{N-(1-anthryl)-N′-[(R)- and/or (S)-3,7-dimethyloctyl]guanidines} J Am Chem Soc 126 2004 3722 3723
58. G. Tian, Y. Lu, and B.M. Novak Helix-sense selective polymerization of carbodiimides: building permanently optically active polymers from achiral monomers J Am Chem Soc 126 2004 4082 4083
59. D.S. Schlitzer, and B.M. Novak Trapped kinetic states, chiral amplification and molecular chaperoning in synthetic polymers: chiral induction in polyguanidines through ion pair interactions J Am Chem Soc 120 1998 2196 2197
60. E. Yashima, K. Maeda, and Y. Okamoto Memory of macromolecular helicity assisted by interaction with achiral small molecules Nature 399 1999 449 451
61. (b) Onouchi H, Kashiwagi D, Hayashi K, Maeda K, Yashima E. Helicity induction on poly(phenylacetylene)s bearing phosphonic acid pendants with chiral amines and memory of the macromolecular helicity assisted by interaction with achiral amines in dimethyl sulfoxide. Macromolecules, 2004;37:5495-503.
62. K. Maeda, K. Morino, Y. Okamoto, T. Sato, and E. Yashima Mechanism of helix induction on a stereoregular poly((4-carboxyphenyl)acetylene) with chiral amines and memory of the macromolecular helicity assisted by interaction with achiral amines J Am Chem Soc 126 2004 4329 4342
63. F. Tanaka Theoretical study of helix induction on a polymer chain by hydrogen-bonding chiral molecules Macromolecules 37 2004 605 613
64. F. Tanaka Theoretical study of helix induction on a polymer chain by hydrogen-bonding chiral molecules Macromolecules 37 2004 605 613
65. L. Brunsveld, J.A.J.M. Vekemans, J.H.K.K. Hirschberg, R.P. Sijbesma, and E.W. Meijer Hierarchical formation of helical supramolecular polymers via stacking of hydrogen-bonded pairs in water Proc Natl Acad Sci USA 99 2002 4977 4982
66. L. Brunsveld, A. Schenning, M.A.C. Broeren, H.M. Janssen, J. Vekemans, and E.W. Meijer Chiral amplification in columns of self-assembled N,N′,N″-tris((S)-3,7-dimethyloctyl)benzene-1,3,5-tricarboxamide in dilute solution Chem Lett 2000 292 293
67. L. Brunsfeld, B.G.G. Lohmeijer, J. Vekemans, and E.W. Meijer Amplification of chirality in helical supramolecular columns J Inclusion Phenom Macrocyclic Chem 41 2001 61 64
68. A.R.A. Palmans, J. Vekemans, E.E. Havinga, and E.W. Meijer Sergeants-and-soldiers principle in chiral columnar stacks of disc-shaped molecules with C-3 symmetry Angew Chem Int Ed 36 1997 2648 2651
69. J.J. van Gorp, J. Vekemans, and E.W. Meijer C-3-symmetrical supramolecular architectures: fibers and organic gels from discotic trisamides and trisureas J Am Chem Soc 124 2002 14759 14769
70. B.M.W. Langeveld-Voss, R.J.M. Waterval, R.A.J. Janssen, and E.W. Meijer Principles of 'majority rules' and 'sergeants and soldiers' applied to the aggregation of optically active polythiophenes: evidence for a multichain phenomenon Macromolecules 32 1999 227 230
71. A. Schenning, A.F.M. Kilbinger, F. Biscarini, M. Cavallini, H.J. Cooper, and P.J. Derrick Supramolecular organization of α,α′- disubstituted sexithiophenes J Am Chem Soc 124 2002 1269 1275
72. J. van Gestel Amplification of chirality in helical supramolecular polymers: the majority-rules principle Macromolecules 37 2004 3894 3898
73. J. Van Gestel, P. Van der Schoot, and M.A.J. Michels Amplification of chirality in helical supramolecular polymers beyond the long-chain limit J Chem Phys 120 2004 8253 8261
74. J. van Gestel, P. van der Schoot, and M.A.J. Michels Amplification of chirality in helical supramolecular polymers Macromolecules 36 2003 6668 6673
75. J. van Gestel, P. van der Schoot, and M.A.J. Michels Role of end effects in helical aggregation Langmuir 19 2003 1375 1383
76. L. Brunsveld, J.A.J.M. Vekemans, J.H.K.K. Hirschberg, R.P. Sijbesma, and E.W. Meijer Hierarchical formation of helical supramolecular polymers via stacking of hydrogen-bonded pairs in water Proc Natl Acad Sci USA 99 2002 4977 4982
77. H. Fenniri, P. Mathivanan, K.L. Vidale, D.M. Sherman, K. Hallenga, and K.V. Wood Helical rosette nanotubes: design self-assembly, and characterization J Am Chem Soc 123 2001 3854 3855
78. H. Fenniri, B.L. Deng, and A.E. Ribbe Helical rosette nanotubes with tunable chiroptical properties J Am Chem Soc 124 2002 11064 11072
79. L. Brunsveld, E.W. Meijer, R.B. Prince, and J.S. Moore Self-assembly of folded m-phenylene ethynylene oligomers into helical columns J Am Chem Soc 123 2001 7978 7984
80. R.B. Prince, J.S. Moore, L. Brunsveld, and E.W. Meijer Cooperativity in the folding of helical m-phenylene ethynylene oligomers based upon the 'sergeants-and-soldiers' principle Chem Eur J 7 2001 4150 4154
81. M.S. Gin, T. Yokozawa, R.B. Prince, and J.S. Moore Helical bias in solvophobically folded oligo(phenylene ethynylene)s J Am Chem Soc 121 1999 2643 2644
82. L.J. Prins, P. Timmerman, and D.N. Reinhoudt Amplification of chirality: the 'sergeants and soldiers' principle applied to dynamic hydrogen-bonded assemblies J Am Chem Soc 123 2001 10153 10163
83. L.J. Prins, E.E. Neuteboom, V. Paraschiv, M. Crego-Calama, P. Timmerman, and D.N. Reinhoudt Kinetic stabilities of double, tetra-, and hexarosette hydrogen-bonded assemblies J Org Chem 67 2002 4808 4820
84. T. Ishi-i, M. Crego-Calama, P. Timmerman, D.N. Reinhoudt, and S. Shinkai Enantioselective formation of a dynamic hydrogen-bonded assembly based on the chiral memory concept J Am Chem Soc 124 2002 14631 14641
85. G.R. Newkome, C.N. Moorefield, and F. Vogtle G.R. Newkome C.N. Moorefield F. Vogtle Dendritic molecules: concepts, syntheses, perspectives 1996 VCH, Weinheim New York
86. For a review, see: A.W. Bosman, H.M. Janssen, and E.W. Meijer About dendrimers: structure, physical properties, and applications Chem Rev 99 1999 1665
87. D.A. Tomalia, H. Baker, J. Dewald, M. Hall, G. Kallos, and S. Martin Dendritic macromolecules: synthesis of starburst dendrimers Macromolecules 19 1986 2466 2468
88. 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 1990 119 157
89. For some reviews of chiral dendrimers, see: (a) H.W.I. Peerlings, and E.W. Meijer Chirality in dendritic architectures Chem Eur J 3 1997 1563 1570
90. D. Seebach, P.B. Rheiner, G. Greiveldinger, T. Butz, and H. Sellner Chiral dendrimers Top Curr Chem 197 1998 125 164
91. C.W. Thomas, and Y. Tor Dendrimers and chirality Chirality 10 1998 53 59
92. B. Ramagnoli, and W. Hayes Chiral dendrimers - from architecturally interesting hyperbranched macromolecules to functional materials J Mater Chem 12 2002 767 799
93. H.-F. Chow, T.K.K. Mong, C.-W. Wan, and Z.Y. Wang Chiral dendrimers Adv Dendritic Macromol 4 1999 107 133
94. S. Rosenfeldt, N. Dingenouts, D. Potschke, M. Ballauff, A.J. Berresheim, and K. Muellen Analysis of the spatial dimensions of fully aromatic dendrimers Angew Chem Int Ed Eng 43 2004 109 112
95. M. Ballauff, and C.N. Likos Dendrimers in solution: insight from theory and simulation Angew Chem Int Ed Eng 43 2004 2998 3020
96. H.M. Harreis, C.N. Likos, and M. Ballauff Can dendrimers be viewed as compact colloids? A simulation study of the fluctuations in a dendrimer of fourth generation J Chem Phys 118 2003 1979 1988
97. K. Karatasos, D.B. Adolf, and G.R. Davies Statics and dynamics of model dendrimers as studied by molecular dynamics simulations J Chem Phys 115 2001 5310 5318
98. M.L. Mansfield Monte carlo studies of dendrimers. Additional results for the diamond lattice model Macromolecules 33 2000 8043 8049
99. Z.Y. Chen, and S.-M. Cui Monte carlo simulations of star-burst dendrimers Macromolecules 29 1996 7943 7952
100. D. Boris, and M. Rubinstein A self-consistent mean field model of a starburst dendrimer: dense core vs dense shell Macromolecules 29 1996 7251 7260
101. M. Murat, and G.S. Grest Molecular dynamics study of dendrimer molecules in solvents of varying quality Macromolecules 29 1996 1278 1285
102. M.L. Mansfield Dendron segregation in model dendrimers Polymer 35 1994 1827 1830
103. M.L. Mansfield, and L.I. Klushin Monte Carlo studies of dendrimer macromolecules Macromolecules 26 1993 4262 4268
104. S. Rosenfeldt, N. Dingenouts, M. Ballauff, N. Werner, F. Voegtle, and P. Lindner Distribution of end groups within a dendritic structure: a sans study including contrast variation Macromolecules 35 2002 8098 8105
105. M. Ballauff Structure of dendrimers in dilute solution Top Curr Chem 212 2001 177 194
106. R.L. Lescanec, and M. Muthukumar Configurational characteristics and scaling behavior of starburst molecules: a computational study Macromolecules 23 1990 2280 2288
107. H.-M. Kao, A.D. Stefanescu, K.L. Wooley, and J. Schaefer Location of terminal groups of dendrimers in the solid state by rotational-echo double-resonance NMR Macromolecules 33 2000 6214 6216
108. T.L. Chasse, R. Sachdeva, Q. Li, Z. Li, R.J. Petrie, and C.B. Gorman Structural effects on encapsulation as probed in redox-active core dendrimer isomers J Am Chem Soc 125 2003 8250 8254
109. I. Bodnar, A.S. Silva, R.W. Deitcher, N.E. Weisman, Y.H. Kim, and N.J. Wagner Structure and rheology of hyperbranched and dendritic polymers. I. Modification and characterization of poly(propyleneimine) dendrimers with acetyl groups J Poly Sci Part B: Poly Phys 38 2000 857 873
110. C. Rosini, S. Superchi, H.W.I. Peerlings, and E.W. Meijer Enantiopure dendrimers derived from the 1,1′-binaphthyl moiety: a correlation between chiroptical properties and conformation of the 1,1′-binaphthyl template Eur J Org Chem 2000 61 71
111. K.J. Naidoo, S.J. Hughes, and J.R. Moss Computational investigations into the potential use of poly(benzyl phenyl ether) dendrimers as supports for organometallic catalysts Macromolecules 32 1999 331 341
112. H.W.I. Peerlings, D.C. Trimbach, and E.W. Meijer Chiral dendrimers with backfolding wedges Chem Commun 1998 497 498
113. K.L. Wooley, C.A. Klug, K. Tasaki, and J. Schaefer Shapes of dendrimers from rotational-echo double-resonance NMR J Am Chem Soc 119 1997 53 58
114. P.G. De Gennes, and H. Hervet Statistics of 'starburst' polymers J Phys Lett 44 1983 351 360
115. S. Rosenfeldt, N. Dingenouts, D. Potschke, M. Ballauff, A.J. Berresheim, and K. Muellen Analysis of the spatial dimensions of fully aromatic dendrimers Angew Chem Int Ed Eng 43 2004 109 112
116. P.K. Maiti, T. Cagin, G. Wang, and W.A. Goddard III Structure of PAMAM dendrimers: generations 1 through 11 Macromolecules 37 2004 6236 6254
117. A. Adhiya, and C. Wesdemiotis Poly(propylene imine) dendrimer conformations in the gas phase: a tandem mass spectrometry study Int J Mass Spectrosc 214 2002 75 88
118. C.S. Cameron, and C.B. Gorman Effects of site encapsulation on electrochemical behavior of redox-active core dendrimers Adv Funct Mater 12 2002 17 20
119. For a discussion of the relationship of optical activity to conformation in linear polymers, see: (a) M. Farina The stereochemistry of linear macromolecules Top Stereochem 1987 111 171
120. P. Pino, P. Salvadori, E. Chiellini, and P.L. Luisi Optical activity and optical rotatory dispersion in synthetic polymers Pure Appl Chem 16 1968 469 490
121. Dendrimers with chiral branch segments: (a) J.R. McElhanon, and D.V. McGrath Toward chiral polyhydroxylated dendrimers. Preparation and chiroptical properties J Org Chem 65 2000 3525 3529
122. J.R. McElhanon, and D.V. McGrath Constitution, configuration, and the optical activity of chiral dendrimers J Am Chem Soc 120 1998 1647 1656
123. D.M. Junge, and D.V. McGrath Synthesis of optically active chiral shell dendrons Tetrahedron Lett 39 1998 1701 1704
124. D.V. McGrath, M.-J. Wu, and U. Chaudhry An approach to highly functionalized dendrimers from chiral, non-racemic synthetic monomers Tetrahedron Lett 37 1996 6077 6080
125. J.R. McElhanon, M.-J. Wu, M. Escobar, and D.V. McGrath Toward chiral dendrimers with highly functionalized interiors. Dendrons from synthetic AB2 monomers Macromolecules 29 1996 8979 8982
126. H.-T. Chang, C.-T. Chen, T. Kondo, G. Siuzdak, and K.B. Sharpless Asymmetric dihydroxylation enables rapid construction of chiral dendrimers based on 1,2-diols Angew Chem, Int Ed Engl 35 1996 182 186
127. R. Balasubramanian, P. Rao, and U. Maitra First bile acid-derived chiral dendritic species with nanometric dimensions Chem Commun 1999 2353 2354
128. J. Kress, A. Rosner, and A. Hirsch Depsipeptide dendrimers Chem Eur J 6 2000 247 257
129. H.-F. Chow, and C.C. Mak Preparation and structure-chiroptical relationships of tartaric acid-based layer-block chiral dendrimers J Chem Soc, Perkin Trans 1 1997 91 95
130. H.-F. Chow, and C.C. Mak Synthesis and chiroptical properties of layer-block dendrimers Pure Appl Chem 69 1997 483 488
131. C.C. Mak, and H.-F. Chow Synthesis and chiroptical properties of optically active layer-block dendrimers Chem Commun 1996 1185 1186
132. H.-F. Chow, and C.C. Mak Facile preparation of optically active dendritic fragments containing multiple tartrate-derived chiral units Tetrahedron Lett 37 1996 5935 5938
133. H.-F. Chow, L.F. Fok, and C.C. Mak Synthesis and characterization of optically active, homochiral dendrimers Tetrahedron Lett 35 1994 3547 3550
134. H.-F. Chow, and C.C. Mak Synthesis and structure-optical rotation relationships of homochiral, monodisperse, tartaric acid-based dendrimers J Chem Soc, Perkin Trans 1 1994 2223 2228
135. Dendrimers with chiral termini: (a) M.-L. Lartigue, A.-M. Caminade, and J.P. Majoral Chiroptical properties of dendrimers with stereogenic end groups Tetrahedron: Asymm 8 1997 2697 2708
136. J. Issberner, M. Boehme, S. Grimme, M. Nieger, W. Paulus, and F. Voegtle Poly(amine/imine) dendrimers bearing planar chiral terminal groups - synthesis and chiroptical properties Tetrahedron: Asymm 7 1996 2223 2232
137. J. Issberner, M. Boehme, S. Grimme, M. Nieger, W. Paulus, and F. Voegtle Poly(amine/imine) dendrimers bearing planar chiral terminal groups - synthesis and chiroptical properties Tetrahedron: Asymm 7 1996 2223 2232
138. G.R. Newkome, X. Lin, and C.D. Weis Chemistry of micelle series. 23. Polytryptophan terminated dendritic macromolecules Tetrahedron: Asymm 2 1991 957 960
139. J.F.G.A. Jansen, H.W.I. Peerlings, E.M.M. de Brabander-Van den Berg, and E.W. Meijer Optical activity of chiral dendritic surfaces Angew Chem Int Ed Engl 34 1995 1206 1209
140. J.F.G.A. Jansen, E.M.M. de Brabander-van den Berg, and E.W. Meijer Induced chirality of guest molecules encapsulated into a dendritic box Recl Trav Chim Pays-Bas 114 1995 225 230
141. Dendrimers with a chiral central core: (a) D. Seebach, J.M. Lapierre, K. Skobridis, and G. Greiveldinger Chiral tris(hydroxymethyl)methane derivatives as syn-thons for chiral dendrimers Angew Chem 106 1994 457 458
142. D. Seebach, J.-M. Lapierre, G. Greiveldinger, and K. Skobridis Synthesis of chiral starburst dendrimers from PHB-derived triols as central cores Helv Chim Acta 77 1994 1673 1688
143. Q.-S. Hu, V. Pugh, M. Sabat, and L. Pu Structurally rigid and optically active dendrimers J Org Chem 64 1999 7528 7536
144. J.-L. Chaumette, M.J. Laufersweiler, and J.R. Parquette Synthesis and chiroptical properties of dendrimers elaborated from a chiral, nonracemic central core J Org Chem 63 1998 9399 9405
145. J.M. Rohde, and J.R. Parquette Synthesis of dendrimers containing 2,5-anhydro-d-mannitol as a chiral, tetrafunctional central core with C2 symmetry Tetrahedron Lett 39 1998 9161 9164
146. Y.-M. Chen, C.-F. Chen, and F. Xi Chiral dendrimers with axial chirality Chirality 10 1998 661 666
147. M. Dubber, and T.K. Lindhorst Synthesis of chiral carbohydrate-centered dendrimers Chem Commun 1998 1265 1266
148. H.W.I. Peerlings, and E.W. Meijer Synthesis and characterization of axially chiral molecules containing dendritic substituents Eur J Org Chem 1998 573 577
149. Q.-S. Hu, V. Pugh, M. Sabat, and L. Pu Structurally rigid and optically active dendrimers J Org Chem 64 1999 7528 7536
150. E. Diez-Barra, J.C. Garcia-Martinez, R. del Rey, J. Rodriguez-Lopez, F. Giacalone, and J.L. Segura Synthesis and photoluminescent properties of 1,1′-binaphthyl-based chiral phenylenevinylene dendrimers J Org Chem 68 2003 3178 3183
151. Mamdouh W, Ujii H, Dulcey AE, Percec V, De Feyter S, De Schryver FC. Expression of molecular chirality and two-dimensional supramolecular self-assembly of chiral, racemic, and achiral monodendrons at the liquid-solid interface. Langmuir 2004;20:7678-85.
152. B. Huang, and J.R. Parquette Synthesis and structure of intramolecularly hydrogen-bonded dendrons Org Lett 3 2000 239
153. DeMatteo MP, Parquette JR, Hadad CM. Unpublished results.
154. Y. Hamuro, S.J. Geib, and A.D. Hamilton Novel folding patterns in a family of oligoanthranilamides: non-peptide oligomers that form extended helical secondary structures J Am Chem Soc 119 1997 10587
155. Y. Hamuro, S.J. Geib, and A.D. Hamilton Oligoanthranilamides. Non-peptide subunits that show formation of specific secondary structure J Am Chem Soc 118 1996 7529
156. J. Recker, D. Tomcik, and J.R. Parquette Folding dendrons. Development of a solvent, temperature and generation dependent chiral conformational order J Am Chem Soc 122 2000 10298
157. A.J. Preston, G. Fraenkel, A. Chow, J.C. Gallucci, and J.R. Parquette Dynamic helical chirality of an intramolecularly hydrogen-bonded bisoxazoline J Org Chem 68 2003 22
158. For a discussion of the correlated rotation in molecular propellers, see: K. Mislow Stereochemical consequences of correlated rotations in molecular propellers Acc Chem Res 9 1976 26
159. J. Recker, and J.R. Parquette Folding dendrons. The development of solvent, temperature and generation dependent chiral conformational order in intramolecularly hydrogen bonded dendrons J Am Chem Soc 122 2000 10298 10307
160. R. Jaenicke, and G. Bohm The stability of proteins in extreme environments Curr Opin Struct Biol 8 1998 738
161. M. Levitt, M. Gerstein, E. Huang, S. Subbiah, and J. Tsai Protein folding: the endgame Annu Rev Biochem 66 1997 549
162. B. Huang, and J.R. Parquette Effect of an internal anthranilamide turn unit on the structure and conformational stability of helically biased intramolecularly hydrogen-bonded dendrons J Am Chem Soc 123 2001 2689
163. B. Huang, M.A. Prantil, T.L. Gustufson, and J.R. Parquette The effect of global compaction on the local secondary structure of folded dendrimers J Am Chem Soc 125 2003 14518 14530
164. T.V. Chalikian, M. Totrov, R. Abagyan, and K.J. Breslauer The hydration of globular proteins as derived from volume and compressibility measurements: cross correlating thermodynamic and structural data J Mol Biol 260 1996 588
165. M.R. Rauckhorst, P.J. Wilson, S.A. Hatcher, C.M. Hadad, and J.R. Parquette 'Locking' dendrimer conformation through metal coordination Tetrahedron 59 2003 3917
166. A. Chakrabartty, and R.L. Baldwin Stability of alpha-helices Adv Protein Chem 1995 4614
167. A. Chakrabartty, T. Kortemme, and R.L. Baldwin Helix propensities of the amino acids measured in alanine-based peptides without helix-stabilizing side-chain interactions Protein Sci 3 1994 843
168. A. Chakrabartty, J.A. Schellman, and R.L. Baldwin Large differences in the helix propensities of alanine and glycine Nature 351 1991 586
169. C.A. Rohl, A. Chakrabartty, and R.L. Baldwin Helix propagation and N-cap propensities of the amino acids measured in alanine-based peptides in 40 volume percent trifluoroethanol Protein Sci 5 1996 2623
170. C.C. Hyde, S.A. Ahmed, E.A. Padlan, E.W. Miles, and D.R. Davies Three-dimensional structure of the tryptophan synthase α2,β2 multienzyme complex from salmonella typhimurium J Biol Chem 263 1988 17857
171. For some reviews of templated assembled synthetic proteins (TASP), see: (a) M. Mutter, P. Dumy, P. Garrouste, C. Lehmann, M. Mathieu, and C. Peggion Template assembled synthetic proteins (TASP) as functional mimetics of proteins Angew Chem, Int Ed Engl 35 1996 1482
172. G. Tuchscherer, and M. Mutter Template assisted protein de novo design Pure Appl Chem 68 1996 2153
173. G. Tuchscherer, D. Grell, M. Mathieu, and M. Mutter Extending the concept of template-assembled synthetic proteins J Pept Res 54 1999 185
174. J. Aerts Prediction of intrinsic viscosities of dendritic, hyperbranched and branched polymers Comput Theor Polym Sci 8 1998 49 54
175. C. Cai, and Z.Y. Chen Intrinsic viscosity of starburst dendrimers Macromolecules 31 1998 6393 6396
176. T.H. Mourey, S.R. Turner, M. Rubinstein, J.M.J. Frechet, C.J. Hawker, and K.L. Wooley Unique behavior of dendritic macromolecules: intrinsic viscosity of polyether dendrimers Macromolecules 25 1992 2401 2406
177. R. Scherrenberg, B. Coussens, P. van Vliet, G. Edouard, J. Brackman, and E. de Brabander The molecular characteristics of poly(propyleneimine) dendrimers as studied with small-angle neutron scattering, viscosimetry, and molecular dynamics Macromolecules 31 1998 456 461
178. D.M. Junge, and D.V. McGrath J Am Chem Soc 121 1999 4912
179. S. Li, and D.V. McGrath J Am Chem Soc 122 2000 6795
180. L.-X. Liao, D.M. Junge, and D.V. McGrath Macromolecules 35 2002 319
181. L.-X. Liao, F. Stellacci, and D.V. McGrath Photoswitchable flexible and shape-persistent dendrimers: comparison of the interplay between a photochromic azobenzene core and dendrimer structure J Am Chem Soc 126 2004 2181 2185
182. D. Grebel-Koehler, D. Liu, S. De Feyter, V. Enkelmann, T. Weil, and C. Engels Synthesis and photomodulation of rigid polyphenylene dendrimers with an azobenzene core Macromolecules 36 2003 578 590
183. G.S. Kumar, and D.C. Neckers Photochemistry of azobenzene-containing polymers Chem Rev 89 1989 1915 1925