Oligomers of enantiopure bicyclic γ/δ-amino acids (BTAa). 1. Synthesis and conformational analysis of 3-Aza-6,8-dioxabicyclo[3.2.1]octane-7-carboxylic acid oligomers (PolyBTG)

Organic Letters

Volumn 2, Issue 25, 2000, Pages 3987-3990

  Machetti, Fabrizio ^a   Ferrali, Alessandro ^a   Menchi, Gloria ^a   Occhiato, Ernesto G ^a   Guarna, Antonio ^a  

^a UNIVERSITY OF FLORENCE   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000914974     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006548s     Document Type: Article

References (31)

1. For example: Yang, D.; Qu, J.; Li, B.; Ng, F.-F.; Wang, X.-C.; Cheung, K.-K.; Wang, D.-P.; Wu, Y.-D. J. Am. Chem. Soc. 1999, 121, 589-590.
2. (a) Seebach, D.; Abele, S.; Gademann, K.; Guichard, G.; Hintermann, T.; Jaun, B.; Matthews, J. L.; Schreiber, J. Helv. Chim. Acta 1998, 81, 932-976 and references therein.
3. (b) Appella, D. H.; Christianson, L. A.; Klein, D. A.; Richards, M. R.; Powell, D. R.; Gellman, S. H. J. Am. Chem. Soc. 1999, 121, 7574-7581 and references therein.
4. (a) Hintermann, T.; Gademann, K.; Jaun, B.; Seebach, D. Helv. Chim. Acta 1998, 81, 983-1002.
5. (b) Hanessian, S.; Luo, X.; Schaum, R.; Michnick, S. J. Am. Chem. Soc. 1998, 120, 8569-8570.
6. (c) Hanessian, S.; Luo, X.; Schaum, R. Tetrahedron Lett. 1999, 40, 4925-4929.
7. (a) Szabo, L.; Smith, B. L.; McReynolds, K. D.; Parril, A. L.; Morris, E. R.; Gervay, J. J. Org. Chem. 1998, 63, 1074-1078.
8. (b) Smith, M. D.; Claridge, T. D. Tranter, G. E.; Sansom, M. S. P.; W.; Fleet, G. W. J. J. Chem. Soc., Chem. Commun. 1998, 2041-2042.
9. (c) Long, D. D.; Hungerford, N. L.; Smith, M. D.; Brittain, D. E. A.; Marquess, D. G.; Claridge, T. D. W.; Fleet, G. W. J. Tetrahedron Lett. 1999, 40, 2195-2198.
10. (d) Claridge, T. D. W.; Long, D. D.; Hungerford, N. L.; Aplin, R. T.; Smith, M. D.; Marquess, D. G.; Fleet, G. W. J. Tetrahedron Lett. 1999, 40, 2199-2202.
11. (e) Schwalbe, H.; Wermuth, J.; Richter, C.; Szalma, S.; Eschenmoser, A.; Quinkert, G. Helv. Chim. Acta 2000, 83, 1079-1107.
12. Gellman, S. H. Acc. Chem. Res. 1998, 31, 173-180.
13. Appella, D. H.; Christianson, L. A.; Karle, L. I.; Powell, D. R.; Gellman, S. H. J. Am. Chem. Soc. 1999, 121, 6206-6212.
14. Rossi, P.; Felluga, F.; Tecilla, P.; Formaggio, F.; Crisma, M.; Toniolo, C.; Scrimin, P. J. Am. Chem. Soc. 1999, 121, 6948-6948 and references therein.
15. Guarna, A.; Guidi, A.; Machetti, F.; Menchi, G.; Occhiato, E. G.; Scarpi, D.; Sisi, S.; Trabocchi, A. J. Org. Chem. 1999, 64, 7347-7364.
16. We named these compounds BTAa (i.e., Bicycles from Tartaric Acid and Amino acid) using the single letter code of the α-amino acids from which the various type of BTAa's are derived (see ref 8).
17. Seebach, D.; Overhand, M.; Künle, F. N. M.; Martinoni, B.; Obere, L.; Hommel, U.; Widmer, H. Helv. Chim. Acta 1996, 79, 913-941. See also: Ondetti, M. A.; Pluscec, J.; Weaver, E. R.; Williams, N.; Sabo, E. F.; Kocy, O. Chemistry and Biology of Peptides; Ann Arbor Science Publishers: Ann Arbor, 1972; p 525.
18. Seebach, D.; Overhand, M.; Künle, F. N. M.; Martinoni, B.; Obere, L.; Hommel, U.; Widmer, H. Helv. Chim. Acta 1996, 79, 913-941. See also: Ondetti, M. A.; Pluscec, J.; Weaver, E. R.; Williams, N.; Sabo, E. F.; Kocy, O. Chemistry and Biology of Peptides; Ann Arbor Science Publishers: Ann Arbor, 1972; p 525.
19. Dado, G. P.; Gellman, S. H. J. Am. Chem. Soc. 1994, 116, 1054-1062.
20. All new compounds were fully characterized by spectroscopic and analytical means.
21. Molecular modeling calculations (MacroModel v.6.5, Amber forcefield, Monte Carlo conformational search) showed that there is a free rotation around the C(7′) - C(=O) bond. However, the conformations in which the C(=O) bond forms dihedral angles of about 112° and 150° with the C(7′) -O(6) bond are prevailing at room temperature.
22. (a) Woody, R. W. Circular Dichroism: Principles and Applications; VCH: Weinheim, 1994
23. (b) Mulkerrin, M. G. In Spectroscopic Methods for Determining Protein Structure in Solution; Havel, H. A., Ed.; VCH: New York, 1996.
24. For non-hydrogen-bonded secondary structure, see: (a) Kirshenbaum, K.; Barron, A. E.; Goldsmith, R. A.; Armand, P.; Bradley, E. K.; Truong, K. T. V.; Dill, K. A.; Cohen, F. E.; Zuckermann, R. N. Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 4303-4308.
25. (b) Armand, P.; Kirshenbaum, K.; Goldsmith, R. A.; Farr-Jones, S.; Barron, A. E.; Truong, K. T. V.; Dill, K. A.; Mierke, D. F.; Cohen, F. E.; Zuckermann, R. N. Proc, Natl. Acad. Sci. U.S.A. 1998, 95, 4309-4314.
26. (c) Huck, B. R.; Langenhan, J. M.; Gellman, S. Org. Lett. 1999, 1, 1717-1720.
27. (d) Abele, S.; Vögtli, K.; Seebach, D. Helv. Chim. Acta 1999, 82, 1539-1558.
28. (a) Beausoleil, E.; Lubell, W. J. Am. Chem. Soc. 1996, 118, 12902-12908.
29. (b) Wu, W.-J.; Raleigh, P. J. Org. Chem. 1998, 63, 6689-6698.
30. (c) Swarbrick, M. E.; Gosselin, F.; Lubell, W. J. Org. Chem. 1999, 64, 1993-2002
31. (d) Halab, L. Lubell, W. J. Org. Chem. 1999, 64, 3312-3321.