Chiral spaces: Dissymmetric capsules through self-assembly

Science

Volumn 279, Issue 5353, 1998, Pages 1021-1023

  Rivera, José M ^a,b   Martín, Tomás ^b   Rebek Jr , Julius ^b  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

^b SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

TERPENE;

ARTICLE; CHEMICAL REACTION; CHIRALITY; HYDROGEN BOND; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

BICYCLO COMPOUNDS, HETEROCYCLIC; CHEMISTRY, PHYSICAL; DIMERIZATION; HYDROGEN BONDING; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, CHEMICAL; MODELS, MOLECULAR; STEREOISOMERISM; SUCCINIMIDES; THERMODYNAMICS;

EID: 0032512839     PISSN: 00368075     EISSN: None     Source Type: Journal    
DOI: 10.1126/science.279.5353.1021     Document Type: Article

References (25)

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10. For additional examples of chirality through self-assembly, see: M. J. Brienne et al., Tetrahedron Lett. 35, 8157 (1994); A. Bilyk and M. M. Harding, J. Chem. Soc. Chem. Commun. 1995, 1697 (1995); J. Sánchez-Quesada, C. Seel, P. Prados, J. de Mendoza, J. Am. Chem. Soc. 118, 277 (1996); S. B. Lee and J.-I. Hong, Tetrahedron Lett. 37, 8501 (1996); T. Mizutani, S. Yagi, A. Honmaru, H. Ogoshi, J. Am. Chem. Soc. 118, 5318 (1996); E. E. Simanek, S. Qiao, I. S. Choi, G. M. Whitesides, J. Org. Chem. 62, 2619 (1997); L. R. MacGillivray and J. L. Atwood, Nature 389, 469 (1997).
11. For additional examples of chirality through self-assembly, see: M. J. Brienne et al., Tetrahedron Lett. 35, 8157 (1994); A. Bilyk and M. M. Harding, J. Chem. Soc. Chem. Commun. 1995, 1697 (1995); J. Sánchez-Quesada, C. Seel, P. Prados, J. de Mendoza, J. Am. Chem. Soc. 118, 277 (1996); S. B. Lee and J.-I. Hong, Tetrahedron Lett. 37, 8501 (1996); T. Mizutani, S. Yagi, A. Honmaru, H. Ogoshi, J. Am. Chem. Soc. 118, 5318 (1996); E. E. Simanek, S. Qiao, I. S. Choi, G. M. Whitesides, J. Org. Chem. 62, 2619 (1997); L. R. MacGillivray and J. L. Atwood, Nature 389, 469 (1997).
12. For additional examples of chirality through self-assembly, see: M. J. Brienne et al., Tetrahedron Lett. 35, 8157 (1994); A. Bilyk and M. M. Harding, J. Chem. Soc. Chem. Commun. 1995, 1697 (1995); J. Sánchez-Quesada, C. Seel, P. Prados, J. de Mendoza, J. Am. Chem. Soc. 118, 277 (1996); S. B. Lee and J.-I. Hong, Tetrahedron Lett. 37, 8501 (1996); T. Mizutani, S. Yagi, A. Honmaru, H. Ogoshi, J. Am. Chem. Soc. 118, 5318 (1996); E. E. Simanek, S. Qiao, I. S. Choi, G. M. Whitesides, J. Org. Chem. 62, 2619 (1997); L. R. MacGillivray and J. L. Atwood, Nature 389, 469 (1997).
13. For additional examples of chirality through self-assembly, see: M. J. Brienne et al., Tetrahedron Lett. 35, 8157 (1994); A. Bilyk and M. M. Harding, J. Chem. Soc. Chem. Commun. 1995, 1697 (1995); J. Sánchez-Quesada, C. Seel, P. Prados, J. de Mendoza, J. Am. Chem. Soc. 118, 277 (1996); S. B. Lee and J.-I. Hong, Tetrahedron Lett. 37, 8501 (1996); T. Mizutani, S. Yagi, A. Honmaru, H. Ogoshi, J. Am. Chem. Soc. 118, 5318 (1996); E. E. Simanek, S. Qiao, I. S. Choi, G. M. Whitesides, J. Org. Chem. 62, 2619 (1997); L. R. MacGillivray and J. L. Atwood, Nature 389, 469 (1997).
14. For additional examples of chirality through self-assembly, see: M. J. Brienne et al., Tetrahedron Lett. 35, 8157 (1994); A. Bilyk and M. M. Harding, J. Chem. Soc. Chem. Commun. 1995, 1697 (1995); J. Sánchez-Quesada, C. Seel, P. Prados, J. de Mendoza, J. Am. Chem. Soc. 118, 277 (1996); S. B. Lee and J.-I. Hong, Tetrahedron Lett. 37, 8501 (1996); T. Mizutani, S. Yagi, A. Honmaru, H. Ogoshi, J. Am. Chem. Soc. 118, 5318 (1996); E. E. Simanek, S. Qiao, I. S. Choi, G. M. Whitesides, J. Org. Chem. 62, 2619 (1997); L. R. MacGillivray and J. L. Atwood, Nature 389, 469 (1997).
15. For additional examples of chirality through self-assembly, see: M. J. Brienne et al., Tetrahedron Lett. 35, 8157 (1994); A. Bilyk and M. M. Harding, J. Chem. Soc. Chem. Commun. 1995, 1697 (1995); J. Sánchez-Quesada, C. Seel, P. Prados, J. de Mendoza, J. Am. Chem. Soc. 118, 277 (1996); S. B. Lee and J.-I. Hong, Tetrahedron Lett. 37, 8501 (1996); T. Mizutani, S. Yagi, A. Honmaru, H. Ogoshi, J. Am. Chem. Soc. 118, 5318 (1996); E. E. Simanek, S. Qiao, I. S. Choi, G. M. Whitesides, J. Org. Chem. 62, 2619 (1997); L. R. MacGillivray and J. L. Atwood, Nature 389, 469 (1997).
16. For additional examples of chirality through self-assembly, see: M. J. Brienne et al., Tetrahedron Lett. 35, 8157 (1994); A. Bilyk and M. M. Harding, J. Chem. Soc. Chem. Commun. 1995, 1697 (1995); J. Sánchez-Quesada, C. Seel, P. Prados, J. de Mendoza, J. Am. Chem. Soc. 118, 277 (1996); S. B. Lee and J.-I. Hong, Tetrahedron Lett. 37, 8501 (1996); T. Mizutani, S. Yagi, A. Honmaru, H. Ogoshi, J. Am. Chem. Soc. 118, 5318 (1996); E. E. Simanek, S. Qiao, I. S. Choi, G. M. Whitesides, J. Org. Chem. 62, 2619 (1997); L. R. MacGillivray and J. L. Atwood, Nature 389, 469 (1997).
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18. J. M. Rivera-Ortiz, T. Martín, J. Rebek Jr., J. Am. Chem. Soc., in press.
19. Y. Tokunaga and J. Rebek Jr., ibid., J. Am. Chem. Soc. 120, 66 (1998).
20. We performed molecular modeling using MACRO-MODEL 5.5 (Amber* force field): F. Mohamadi et al., J. Comput. Chem. 11, 440 (1990). The volumes for the guests and the cavities were obtained from the GRASP program [A. Nicholls, K. A. Sharp, B. Honig, Proteins 11, 281 (1991)].
21. We performed molecular modeling using MACRO-MODEL 5.5 (Amber* force field): F. Mohamadi et al., J. Comput. Chem. 11, 440 (1990). The volumes for the guests and the cavities were obtained from the GRASP program [A. Nicholls, K. A. Sharp, B. Honig, Proteins 11, 281 (1991)].
22. S. Mecozzi and J. Rebek Jr., Chem. Eur J., in press.
23. gB is the integral for the signal of the guest in complex B; h is the initial amount of monomer (in millimoles); g is the amount (in millimoles) of guest added to the solution; a is the amount of guest (in millimoles) in complex A; b is the amount of guest (in millimoles) in complex B; and V is the total volume (in milliliters).
24. R. K. Castellano, B. H. Kim, J. Rebek Jr., J. Am. Chem. Soc. 119, 12671 (1997).
25. This research was supported by the Skaggs Research Foundation and NIH. We thank U. Obst for advice on molecular dynamics studies. Administración de Fomento Económico of Puerto Rico provided fellowship support to J.M.R. The Ministerio de Educación y Cultura of Spain provided fellowship support to T. M.