Molecular description of the propagation of chirality from molecules to complex systems: Different mechanisms controlled by hydrophobic interactions

Chemistry - A European Journal

Volumn 18, Issue 46, 2012, Pages 14680-14688

  Marinelli, Fabrizio ^a   Sorrenti, Alessandro ^b,c   Corvaglia, Valentina ^b   Leone, Vanessa ^a   Mancini, Giovanna ^b,c  

^a MAX PLANCK INSTITUTE OF BIOPHYSICS   (Germany)

^b SAPIENZA UNIVERSITY OF ROME   (Italy)

^c Ctro di Eccellenza Materiali Innovativi Nanostrutturati per Applicazioni Chim Fisiche e Biomed   (Italy)

Author keywords

chirality transfer; circular dichroism; hydrophobic interactions; metadynamics; self assembly

Indexed keywords

CHIRAL CONFORMERS; CHIRAL INFORMATION; CHIRALITY TRANSFER; DIFFERENT MECHANISMS; DYE MOLECULE; EXPERIMENTAL APPROACHES; HELICAL HANDEDNESS; HETERO-AGGREGATES; HYDROPHOBIC CHAINS; HYDROPHOBIC INTERACTIONS; HYDROPHOBIC MOIETIES; METADYNAMICS; MOLECULAR DESCRIPTIONS; MOLECULAR LEVELS; RELATIVE CONCENTRATION; SURFACTANT MOLECULES; TOPOLOGICAL ARRANGEMENT;

CHIRALITY; DICHROISM; ENANTIOMERS; HYDROPHOBICITY; MOLECULES; SELF ASSEMBLY; SURFACE ACTIVE AGENTS;

STEREOCHEMISTRY;

SURFACTANT;

ARTICLE; CHEMICAL PHENOMENA; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; STEREOISOMERISM; SURFACE PROPERTY; THEORETICAL MODEL;

HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; MODELS, THEORETICAL; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; STEREOISOMERISM; SURFACE PROPERTIES; SURFACE-ACTIVE AGENTS;

EID: 84868688876     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201202342     Document Type: Article

References (52)

1. L. Addadi, S. Weiner, Nature 2001, 411, 753-755.
2. J. R. Young, S. A. Davis, P. R. Bown, S. Mann, J. Struct. Biol. 1999, 126, 195-215.
3. C. A. Orme, A. Noy, A. Wierzbicki, M. T. McBride, M. Grantham, H. H. Teng, P. M. Dove, J. J. DeYoreo, Nature 2001, 411, 775-779.
4. N. Bouropoulos, S. Weiner, L. Addadi, Chem. Eur. J. 2001, 7, 1881-1888.
5. H. Zepik, E. Shavit, M. Tang, T. R. Jensen, K. Kjaer, G. Bolbach, L. Leiserowitz, I. Weissbuch, M. Lahav, Science 2002, 295, 1266-1269.
6. R. A. Illos, F. R. Bisogno, G. Clodic, G. Bolbach, I. Weissbucht, M. Lahav, J. Am. Chem. Soc. 2008, 130, 8651-8659.
7. I. Weissbuch, M. Lahav, Chem. Rev. 2011, 111, 3236-3267.
8. I. Danila, F. Riobe, F. Piron, J. Puigmarti-Luis, J. D. Wallis, M. Linares, H. Agren, D. Beljonne, D. B. Amabilino, N. Avarvari, J. Am. Chem. Soc. 2011, 133, 8344-8353.
9. F. J. M. Hoeben, P. Jonkheijm, E. W. Meijer, A. P. H. J. Schenning, Chem. Rev. 2005, 105, 1491-1546.
10. N. Ousaka, Y. Takeyama, H. Iida, E. Yashima, Nat. Chem. 2011, 3, 856-861.
11. P. Walde, E. Blochliger, K. Morigaki, Langmuir 1999, 15, 2346-2350.
12. C. Bombelli, S. Borocci, F. Lupi, G. Mancini, L. Mannina, A. L. Segre, S. Viel, J. Am. Chem. Soc. 2004, 126, 13354-13362.
13. F. Ceccacci, G. Mancini, A. Sferrazza, C. Villani, J. Am. Chem. Soc. 2005, 127, 13762-13763.
14. F. Ceccacci, L. Giansanti, G. Mancini, P. Mencarelli, A. Sorrenti, New J. Chem. 2007, 31, 86-92.
15. H. Nakagawa, Y. Kobori, M. Yoshida, K. Yamada, Chem. Commun. 2001, 2692-2693.
16. S. Lalitha, A. S. Kumar, K. J. Stine, D. F. Covey, Chem. Commun. 2001, 1192-1193.
17. S. Pathirana, W. C. Neely, L. J. Myers, V. Vodyanoy, J. Am. Chem. Soc. 1992, 114, 1404-1405.
18. C. Bombelli, C. Bernardini, G. Elemento, G. Mancini, A. Sorrenti, C. Villani, J. Am. Chem. Soc. 2008, 130, 2732.
19. Z. El-Hachemi, G. Mancini, J. M. Ribo, A. Sorrenti, J. Am. Chem. Soc. 2008, 130, 15176-15184.
20. R. Andreani, C. Bombelli, S. Borocci, J. Lah, G. Mancini, P. Mencarelli, G. Vesnaver, C. Villani, Tetrahedron: Asymmetry 2004, 15, 987-994.
21. P. Job, Annales De Chimie France 1928, 9, 113-203.
22. F. J. C. Rossotti, H. Rossotti, The Determination of Stability Constants, McGraw-Hill, New York, 1961.
23. P. Forte-Tavčer, Dyes Pigm. 2004, 63, 181-189.
24. B. Kahr, W. Kaminsky, K. Claborn, J. Phys. Org. Chem. 2004, 17, 735-739.
25. N. Harada, K. Nakanishi, Circular Dichroic Spectroscopy: Exciton Coupling in Organic Chemistry, Oxford University Press, Oxford 1983.
26. T. M. Cooper, M. O. Stone, Langmuir 1998, 14, 6662-6668.
27. A. Laio, M. Parrinello, Proc. Natl. Acad. Sci. USA 2002, 99, 12562-12566.
28. Y. Crespo, F. Marinelli, F. Pietrucci, A. Laio, Phys. Rev. E 2010, 81, 055701.
29. A. Laio, F. L. Gervasio, Rep. Prog. Phys. 2008, 71, 126601.
30. N. Harada, K. Nakanishi, Acc. Chem. Res. 1972, 5, 257.
31. X. Daura, K. Gademann, B. Jaun, D. Seebach, W. F. van Gunsteren, A. E. Mark, Angew. Chem. 1999, 111, 249-253
32. Angew. Chem. Int. Ed. 1999, 38, 236-240.
33. R. T. Buwalda, J. M. Jonker, J. B. F. N. Engberts, Langmuir 1999, 15, 1083-1089.
34. R. T. Buwalda, J. B. F. N. Engberts, Langmuir 2001, 17, 1054-1059.
35. B. Simončič, J. Åpan, Dyes Pigm. 1998, 36, 1-14.
36. B. Simončič, J. Åpan, Dyes Pigm. 2000, 46, 1-8.
37. A. R. Tehrani Bagha, H. Bahrami, B. Movassagh, M. Arami, F. M. Menger, Dyes Pigm. 2007, 72, 331-338.
38. E. G. Mcrae, M. Kasha, J. Chem. Phys. 1958, 28, 721-722.
39. Z. El-Hachemi, G. Mancini, J. M. Ribo, A. Sorrenti, New J. Chem. 2010, 34, 260-266.
40. M. Crego-Calama, D. N. Reinhoudt, Supramolecular Chirality, Springer, Heidelberg, 2006.
41. F. Marinelli, F. Pietrucci, A. Laio, S. Piana, PLoS Comput. Biol. 2009, 5, e 1000452.
42. S. Piana, A. Laio, J. Phys. Chem. B 2007, 111, 4553-4559.
43. P. Cossio, F. Marinelli, A. Laio, F. Pietrucci, J. Phys. Chem. B 2010, 114, 3259-3265.
44. F. Marinelli, S. I. Kuhlmann, E. Grell, H. J. Kunte, C. Ziegler, J. D. Faraldo-Gomez, Proc. Natl. Acad. Sci. USA 2011, 108, E 1285 -E 1292.
45. V. Leone, G. Lattanzi, C. Molteni, P. Carloni, PLoS Comput. Biol. 2009, 5, e 1000309.
46. X. Biarnés, F. Pietrucci, F. Marinelli, A. Laio, Comput. Phys. Commun. 2012, 183, 203-211.
47. S. Woodcock, B. Henrissat, J. Sugiyama, Biopolymers 1995, 36, 201-210.
48. C. T. Lee, W. T. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785-789.
49. A. D. Becke, J. Chem. Phys. 1993, 98, 5648-5652.
50. S. H. Vosko, L. Wilk, Phys. Rev. B 1980, 22, 3812-3815.
51. P. J. Stephens, F. J. Devlin, C. F. Chabalowski, M. J. Frisch, J. Phys. Chem. 1994, 98, 11623-11627.
52. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. Montgomery, J. A., J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, N. J. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, Ã. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, D. J. Fox in Gaussian, Vol. (Ed. A1), Wallingford CT, 2009.