Specific autocatalysis in diastereoisomeric replicators

Organic Letters

Volumn 7, Issue 18, 2005, Pages 3833-3836

  Kassianidis, Eleftherios ^a   Pearson, Russell J ^a   Philp, Douglas ^a  

^a UNIVERSITY OF ST ANDREWS   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 24944498176     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol051179r     Document Type: Article

References (22)

1. (a) von Kiedrowski, G.; Eckardt, L.-H.; Naumann, K.; Pankau, W. M.; Reimold, M.; Rein, M. Pure Appl. Chem. 2003, 75, 609-619.
2. (b) Schrader, T.; Hamilton, A. D., Eds. Functional Synthetic Receptors; Wiley-VCH: Weinheim, 2005.
3. For examples of complex replicable entities, see: (a) Zykov, V.; Mytilinaios, E.; Adams, B.; Lipson, H. Nature 2005, 435, 163-164.
4. (b) Eckardt, L.-H.; Naumann, K.; Pankau, W. M.; Rein, M.; Schweitzer, M.; Windhab, N.; von Kiedrowski, G. Nature 2002, 420, 286-288.
5. (c) Szostak, J. W.; Bartel, D. P.; Luisi, P. L. Nature 2001, 409, 387-390.
6. For reviews, see: (a) Robertson, A.; Sinclair, A. J.; Philp, D. Chem. Soc. Rev. 2000, 29, 141-152.
7. (b) Wintner, E. A.; Rebek, J., Jr. Acta Chem. Scand. 1996, 50, 469-485.
8. (c) Li, X.; Chmielewski, J. Org. Biomol. Chem. 2003, 1, 901-904.
9. (d) Isaac, R.; Ham, Y.-W.; Chmielewski, J. Curr. Opin. Struct. Biol. 2001, 11, 458-463.
10. (e) Lee, D. H.; Severin, K.; Ghadiri, M. R. Curr. Opin. Chem. Biol. 1997, 1, 491-496.
11. (f) Bag, B. G.; von Kiedrowski, G. Pure Appl. Chem. 1996, 68, 2145-2152.
12. von Kiedrowski, G. Angew. Chem., Int. Ed. Engl. 1986, 25, 932-935.
13. (a) Bennes, R. M.; Sapro-Babiloni, M.; Hayes W. C.; Philp, D. Tetrahedron Lett. 2001, 42, 2377-2380.
14. (b) Howell, S. J.; Philp, D.; Spencer, N. Tetrahedron 2001, 57, 4945-4954.
15. (c) Pearson, R. J.; Kassianidis, E.; Philp, D. Tetrahedron Lett. 2004, 45, 4777-4780.
16. (a) Quayle, J. M.; Slawin, A. M. Z.; Philp, D. Tetrahedron Lett. 2002, 43, 7229-7233.
17. (b) Allen, V. C.; Philp, D.; Spencer, N. Org. Lett. 2001, 3, 777-780;
18. Pearson, R. J.; Kassianidis E.; Slawin A. M. Z.; Philp, D. Org. Biomol. Chem. 2004, 2, 3434-3441.
19. Sinclair, A. J., Ph.D. Thesis, University of Birmingham, Birmingham, UK, 2000.
20. All of the experiments reported here were performed using racemic mixtures of exo-5 and endo-5. We recognize that a more complex hypercyclic network involving individual enantiomers could exist in this system. However, since we have been unable to resolve the cycloadducts, we prefer to base our analysis on a model we can test experimentally.
21. Molecular mechanics calculations were carried out using the AMBER* force field as implemented in Macromodel (version 7.1; Schrödinger, Inc.: Portland, OR, 2000) running on a Linux workstation.
22. Cacciapaglia, R.; Di Stefano, S.; Mandolini, L. Acc. Chem. Res. 2004, 37, 113-122.