Synthesis and conformational study of homo-peptides based on (S)-Bin, a C2-symmetric binaphthyl-derived Cα,α-disubstituted glycine with only axial chirality

Tetrahedron Asymmetry

Volumn 14, Issue 13, 2003, Pages 1879-1893

  Mazaleyrat, Jean Paul ^a   Wright, Karen ^a   Gaucher, Anne ^a   Wakselman, Michel ^a   Oancea, Simona ^b   Formaggio, Fernando ^b   Toniolo, Claudio ^b   Setnička, Vladimir ^c   Kapitán, Josef ^c   Keiderling, Timothy A ^c  

^a LABORATOIRE DES SCIENCES DU CLIMAT ET DE L ENVIRONNEMENT   (France)

^b UNIVERSITY OF PADOVA   (Italy)

^c UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FLUORIDE; GLYCINE DERIVATIVE; NAPHTHYL GROUP; OLIGOMER; PEPTIDE DERIVATIVE;

ARTICLE; CALCULATION; CHIRALITY; CIRCULAR DICHROISM; INFRARED SPECTROSCOPY; PEPTIDE SYNTHESIS; PRIORITY JOURNAL; PROTEIN CONFORMATION; PROTEIN SECONDARY STRUCTURE; SPECTROSCOPY;

EID: 0038433321     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(03)00285-4     Document Type: Article

References (80)

1. α,α-disubstituted glycines and their peptides, see: (a) Marshall, G. R. In Intra-Science Chemistry Report; Kharasch, N., Ed.; Gordon and Breach: New York, 1971; pp. 305-316; (b) Karle, I. L.; Balaram, P. Biochemistry 1990, 29, 6747-6756; (c) Toniolo, C.; Benedetti, E. Macromolecules 1991, 24, 4004-4009; (d) Toniolo, C.; Benedetti, E. Trends Biochem. Sci. 1991, 16, 350-353; (e) Balaram, P. Curr. Opin. Struct. Biol. 1992, 2, 845-851; (f) Toniolo, C. Janssen Chim. Acta 1993, 11, 10-16; (g) Benedetti, E. Biopolymers 1996, 40, 3-44; (h) Karle, I. L. Biopolymers 1996, 40, 157-180; (i) Karle, I. L. Acc. Chem. Res. 1999, 32, 693-701; (j) Andrews, M. J. I.; Tabor, A. B. Tetrahedron 1999, 55, 11711-11743; (k) Toniolo, C.; Crisma, M.; Formaggio, F.; Peggion, C. Biopolymers (Peptide Sci.) 2001, 60, 396-419; (l) Toniolo, C.; Benedetti, E. In Molecular Conformation and Biological Interactions; Balaram, P.; Ramaseshan, S., Eds.; Indian Academy of Sciences: Bangalore, 1991; pp. 511-521.
2. α,α-disubstituted glycines and their peptides, see: (a) Marshall, G. R. In Intra-Science Chemistry Report; Kharasch, N., Ed.; Gordon and Breach: New York, 1971; pp. 305-316; (b) Karle, I. L.; Balaram, P. Biochemistry 1990, 29, 6747-6756; (c) Toniolo, C.; Benedetti, E. Macromolecules 1991, 24, 4004-4009; (d) Toniolo, C.; Benedetti, E. Trends Biochem. Sci. 1991, 16, 350-353; (e) Balaram, P. Curr. Opin. Struct. Biol. 1992, 2, 845-851; (f) Toniolo, C. Janssen Chim. Acta 1993, 11, 10-16; (g) Benedetti, E. Biopolymers 1996, 40, 3-44; (h) Karle, I. L. Biopolymers 1996, 40, 157-180; (i) Karle, I. L. Acc. Chem. Res. 1999, 32, 693-701; (j) Andrews, M. J. I.; Tabor, A. B. Tetrahedron 1999, 55, 11711-11743; (k) Toniolo, C.; Crisma, M.; Formaggio, F.; Peggion, C. Biopolymers (Peptide Sci.) 2001, 60, 396-419; (l) Toniolo, C.; Benedetti, E. In Molecular Conformation and Biological Interactions; Balaram, P.; Ramaseshan, S., Eds.; Indian Academy of Sciences: Bangalore, 1991; pp. 511-521.
3. α,α-disubstituted glycines and their peptides, see: (a) Marshall, G. R. In Intra-Science Chemistry Report; Kharasch, N., Ed.; Gordon and Breach: New York, 1971; pp. 305-316; (b) Karle, I. L.; Balaram, P. Biochemistry 1990, 29, 6747-6756; (c) Toniolo, C.; Benedetti, E. Macromolecules 1991, 24, 4004-4009; (d) Toniolo, C.; Benedetti, E. Trends Biochem. Sci. 1991, 16, 350-353; (e) Balaram, P. Curr. Opin. Struct. Biol. 1992, 2, 845-851; (f) Toniolo, C. Janssen Chim. Acta 1993, 11, 10-16; (g) Benedetti, E. Biopolymers 1996, 40, 3-44; (h) Karle, I. L. Biopolymers 1996, 40, 157-180; (i) Karle, I. L. Acc. Chem. Res. 1999, 32, 693-701; (j) Andrews, M. J. I.; Tabor, A. B. Tetrahedron 1999, 55, 11711-11743; (k) Toniolo, C.; Crisma, M.; Formaggio, F.; Peggion, C. Biopolymers (Peptide Sci.) 2001, 60, 396-419; (l) Toniolo, C.; Benedetti, E. In Molecular Conformation and Biological Interactions; Balaram, P.; Ramaseshan, S., Eds.; Indian Academy of Sciences: Bangalore, 1991; pp. 511-521.
4. α,α-disubstituted glycines and their peptides, see: (a) Marshall, G. R. In Intra-Science Chemistry Report; Kharasch, N., Ed.; Gordon and Breach: New York, 1971; pp. 305-316; (b) Karle, I. L.; Balaram, P. Biochemistry 1990, 29, 6747-6756; (c) Toniolo, C.; Benedetti, E. Macromolecules 1991, 24, 4004-4009; (d) Toniolo, C.; Benedetti, E. Trends Biochem. Sci. 1991, 16, 350-353; (e) Balaram, P. Curr. Opin. Struct. Biol. 1992, 2, 845-851; (f) Toniolo, C. Janssen Chim. Acta 1993, 11, 10-16; (g) Benedetti, E. Biopolymers 1996, 40, 3-44; (h) Karle, I. L. Biopolymers 1996, 40, 157-180; (i) Karle, I. L. Acc. Chem. Res. 1999, 32, 693-701; (j) Andrews, M. J. I.; Tabor, A. B. Tetrahedron 1999, 55, 11711-11743; (k) Toniolo, C.; Crisma, M.; Formaggio, F.; Peggion, C. Biopolymers (Peptide Sci.) 2001, 60, 396-419; (l) Toniolo, C.; Benedetti, E. In Molecular Conformation and Biological Interactions; Balaram, P.; Ramaseshan, S., Eds.; Indian Academy of Sciences: Bangalore, 1991; pp. 511-521.
5. α,α-disubstituted glycines and their peptides, see: (a) Marshall, G. R. In Intra-Science Chemistry Report; Kharasch, N., Ed.; Gordon and Breach: New York, 1971; pp. 305-316; (b) Karle, I. L.; Balaram, P. Biochemistry 1990, 29, 6747-6756; (c) Toniolo, C.; Benedetti, E. Macromolecules 1991, 24, 4004-4009; (d) Toniolo, C.; Benedetti, E. Trends Biochem. Sci. 1991, 16, 350-353; (e) Balaram, P. Curr. Opin. Struct. Biol. 1992, 2, 845-851; (f) Toniolo, C. Janssen Chim. Acta 1993, 11, 10-16; (g) Benedetti, E. Biopolymers 1996, 40, 3-44; (h) Karle, I. L. Biopolymers 1996, 40, 157-180; (i) Karle, I. L. Acc. Chem. Res. 1999, 32, 693-701; (j) Andrews, M. J. I.; Tabor, A. B. Tetrahedron 1999, 55, 11711-11743; (k) Toniolo, C.; Crisma, M.; Formaggio, F.; Peggion, C. Biopolymers (Peptide Sci.) 2001, 60, 396-419; (l) Toniolo, C.; Benedetti, E. In Molecular Conformation and Biological Interactions; Balaram, P.; Ramaseshan, S., Eds.; Indian Academy of Sciences: Bangalore, 1991; pp. 511-521.
6. α,α-disubstituted glycines and their peptides, see: (a) Marshall, G. R. In Intra-Science Chemistry Report; Kharasch, N., Ed.; Gordon and Breach: New York, 1971; pp. 305-316; (b) Karle, I. L.; Balaram, P. Biochemistry 1990, 29, 6747-6756; (c) Toniolo, C.; Benedetti, E. Macromolecules 1991, 24, 4004-4009; (d) Toniolo, C.; Benedetti, E. Trends Biochem. Sci. 1991, 16, 350-353; (e) Balaram, P. Curr. Opin. Struct. Biol. 1992, 2, 845-851; (f) Toniolo, C. Janssen Chim. Acta 1993, 11, 10-16; (g) Benedetti, E. Biopolymers 1996, 40, 3-44; (h) Karle, I. L. Biopolymers 1996, 40, 157-180; (i) Karle, I. L. Acc. Chem. Res. 1999, 32, 693-701; (j) Andrews, M. J. I.; Tabor, A. B. Tetrahedron 1999, 55, 11711-11743; (k) Toniolo, C.; Crisma, M.; Formaggio, F.; Peggion, C. Biopolymers (Peptide Sci.) 2001, 60, 396-419; (l) Toniolo, C.; Benedetti, E. In Molecular Conformation and Biological Interactions; Balaram, P.; Ramaseshan, S., Eds.; Indian Academy of Sciences: Bangalore, 1991; pp. 511-521.
7. α,α-disubstituted glycines and their peptides, see: (a) Marshall, G. R. In Intra-Science Chemistry Report; Kharasch, N., Ed.; Gordon and Breach: New York, 1971; pp. 305-316; (b) Karle, I. L.; Balaram, P. Biochemistry 1990, 29, 6747-6756; (c) Toniolo, C.; Benedetti, E. Macromolecules 1991, 24, 4004-4009; (d) Toniolo, C.; Benedetti, E. Trends Biochem. Sci. 1991, 16, 350-353; (e) Balaram, P. Curr. Opin. Struct. Biol. 1992, 2, 845-851; (f) Toniolo, C. Janssen Chim. Acta 1993, 11, 10-16; (g) Benedetti, E. Biopolymers 1996, 40, 3-44; (h) Karle, I. L. Biopolymers 1996, 40, 157-180; (i) Karle, I. L. Acc. Chem. Res. 1999, 32, 693-701; (j) Andrews, M. J. I.; Tabor, A. B. Tetrahedron 1999, 55, 11711-11743; (k) Toniolo, C.; Crisma, M.; Formaggio, F.; Peggion, C. Biopolymers (Peptide Sci.) 2001, 60, 396-419; (l) Toniolo, C.; Benedetti, E. In Molecular Conformation and Biological Interactions; Balaram, P.; Ramaseshan, S., Eds.; Indian Academy of Sciences: Bangalore, 1991; pp. 511-521.
8. α,α-disubstituted glycines and their peptides, see: (a) Marshall, G. R. In Intra-Science Chemistry Report; Kharasch, N., Ed.; Gordon and Breach: New York, 1971; pp. 305-316; (b) Karle, I. L.; Balaram, P. Biochemistry 1990, 29, 6747-6756; (c) Toniolo, C.; Benedetti, E. Macromolecules 1991, 24, 4004-4009; (d) Toniolo, C.; Benedetti, E. Trends Biochem. Sci. 1991, 16, 350-353; (e) Balaram, P. Curr. Opin. Struct. Biol. 1992, 2, 845-851; (f) Toniolo, C. Janssen Chim. Acta 1993, 11, 10-16; (g) Benedetti, E. Biopolymers 1996, 40, 3-44; (h) Karle, I. L. Biopolymers 1996, 40, 157-180; (i) Karle, I. L. Acc. Chem. Res. 1999, 32, 693-701; (j) Andrews, M. J. I.; Tabor, A. B. Tetrahedron 1999, 55, 11711-11743; (k) Toniolo, C.; Crisma, M.; Formaggio, F.; Peggion, C. Biopolymers (Peptide Sci.) 2001, 60, 396-419; (l) Toniolo, C.; Benedetti, E. In Molecular Conformation and Biological Interactions; Balaram, P.; Ramaseshan, S., Eds.; Indian Academy of Sciences: Bangalore, 1991; pp. 511-521.
9. α,α-disubstituted glycines and their peptides, see: (a) Marshall, G. R. In Intra-Science Chemistry Report; Kharasch, N., Ed.; Gordon and Breach: New York, 1971; pp. 305-316; (b) Karle, I. L.; Balaram, P. Biochemistry 1990, 29, 6747-6756; (c) Toniolo, C.; Benedetti, E. Macromolecules 1991, 24, 4004-4009; (d) Toniolo, C.; Benedetti, E. Trends Biochem. Sci. 1991, 16, 350-353; (e) Balaram, P. Curr. Opin. Struct. Biol. 1992, 2, 845-851; (f) Toniolo, C. Janssen Chim. Acta 1993, 11, 10-16; (g) Benedetti, E. Biopolymers 1996, 40, 3-44; (h) Karle, I. L. Biopolymers 1996, 40, 157-180; (i) Karle, I. L. Acc. Chem. Res. 1999, 32, 693-701; (j) Andrews, M. J. I.; Tabor, A. B. Tetrahedron 1999, 55, 11711-11743; (k) Toniolo, C.; Crisma, M.; Formaggio, F.; Peggion, C. Biopolymers (Peptide Sci.) 2001, 60, 396-419; (l) Toniolo, C.; Benedetti, E. In Molecular Conformation and Biological Interactions; Balaram, P.; Ramaseshan, S., Eds.; Indian Academy of Sciences: Bangalore, 1991; pp. 511-521.
10. α,α-disubstituted glycines and their peptides, see: (a) Marshall, G. R. In Intra-Science Chemistry Report; Kharasch, N., Ed.; Gordon and Breach: New York, 1971; pp. 305-316; (b) Karle, I. L.; Balaram, P. Biochemistry 1990, 29, 6747-6756; (c) Toniolo, C.; Benedetti, E. Macromolecules 1991, 24, 4004-4009; (d) Toniolo, C.; Benedetti, E. Trends Biochem. Sci. 1991, 16, 350-353; (e) Balaram, P. Curr. Opin. Struct. Biol. 1992, 2, 845-851; (f) Toniolo, C. Janssen Chim. Acta 1993, 11, 10-16; (g) Benedetti, E. Biopolymers 1996, 40, 3-44; (h) Karle, I. L. Biopolymers 1996, 40, 157-180; (i) Karle, I. L. Acc. Chem. Res. 1999, 32, 693-701; (j) Andrews, M. J. I.; Tabor, A. B. Tetrahedron 1999, 55, 11711-11743; (k) Toniolo, C.; Crisma, M.; Formaggio, F.; Peggion, C. Biopolymers (Peptide Sci.) 2001, 60, 396-419; (l) Toniolo, C.; Benedetti, E. In Molecular Conformation and Biological Interactions; Balaram, P.; Ramaseshan, S., Eds.; Indian Academy of Sciences: Bangalore, 1991; pp. 511-521.
11. α,α-disubstituted glycines and their peptides, see: (a) Marshall, G. R. In Intra-Science Chemistry Report; Kharasch, N., Ed.; Gordon and Breach: New York, 1971; pp. 305-316; (b) Karle, I. L.; Balaram, P. Biochemistry 1990, 29, 6747-6756; (c) Toniolo, C.; Benedetti, E. Macromolecules 1991, 24, 4004-4009; (d) Toniolo, C.; Benedetti, E. Trends Biochem. Sci. 1991, 16, 350-353; (e) Balaram, P. Curr. Opin. Struct. Biol. 1992, 2, 845-851; (f) Toniolo, C. Janssen Chim. Acta 1993, 11, 10-16; (g) Benedetti, E. Biopolymers 1996, 40, 3-44; (h) Karle, I. L. Biopolymers 1996, 40, 157-180; (i) Karle, I. L. Acc. Chem. Res. 1999, 32, 693-701; (j) Andrews, M. J. I.; Tabor, A. B. Tetrahedron 1999, 55, 11711-11743; (k) Toniolo, C.; Crisma, M.; Formaggio, F.; Peggion, C. Biopolymers (Peptide Sci.) 2001, 60, 396-419; (l) Toniolo, C.; Benedetti, E. In Molecular Conformation and Biological Interactions; Balaram, P.; Ramaseshan, S., Eds.; Indian Academy of Sciences: Bangalore, 1991; pp. 511-521.
12. α,α-disubstituted glycines and their peptides, see: (a) Marshall, G. R. In Intra-Science Chemistry Report; Kharasch, N., Ed.; Gordon and Breach: New York, 1971; pp. 305-316; (b) Karle, I. L.; Balaram, P. Biochemistry 1990, 29, 6747-6756; (c) Toniolo, C.; Benedetti, E. Macromolecules 1991, 24, 4004-4009; (d) Toniolo, C.; Benedetti, E. Trends Biochem. Sci. 1991, 16, 350-353; (e) Balaram, P. Curr. Opin. Struct. Biol. 1992, 2, 845-851; (f) Toniolo, C. Janssen Chim. Acta 1993, 11, 10-16; (g) Benedetti, E. Biopolymers 1996, 40, 3-44; (h) Karle, I. L. Biopolymers 1996, 40, 157-180; (i) Karle, I. L. Acc. Chem. Res. 1999, 32, 693-701; (j) Andrews, M. J. I.; Tabor, A. B. Tetrahedron 1999, 55, 11711-11743; (k) Toniolo, C.; Crisma, M.; Formaggio, F.; Peggion, C. Biopolymers (Peptide Sci.) 2001, 60, 396-419; (l) Toniolo, C.; Benedetti, E. In Molecular Conformation and Biological Interactions; Balaram, P.; Ramaseshan, S., Eds.; Indian Academy of Sciences: Bangalore, 1991; pp. 511-521.
13. Valle G., Crisma M., Bonora G.M., Toniolo C., Lelj F., Barone V., Fraternali F., Hardy P.M., Langran-Goldsmith A., Maia H.L.S. J. Chem. Soc., Perkin Trans. 2. 1990;1481-1487.
14. Crisma M., Valle G., Bonora G.M., Toniolo C., Lelj F., Barone V., Fraternali F., Hardy P.M., Maia H.L.S. Biopolymers. 31:1991;637-641.
15. Valle G., Crisma M., Toniolo C., Rao R.B., Sukumar M., Balaram P. Int. J. Peptide Protein Res. 38:1991;511-518.
16. Toniolo C., Crisma M., Formaggio F., Benedetti E., Santini A., Iacovino R., Saviano M., Di Blasio B., Pedone C., Kamphuis J. Biopolymers. 40:1996;519-522.
17. Benedetti E., Di Blasio B., Iacovino R., Menchise V., Saviano M., Pedone C., Bonora G.M., Ettorre A., Graci L., Formaggio F., Crisma M., Valle G., Toniolo C. J. Chem. Soc., Perkin Trans. 2. 1997;2023-2032.
18. Mazaleyrat J.-P., Gaucher A., Wakselman M., Tchertanov L., Guilhem J. Tetrahedron Lett. 37:1996;2971-2974.
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21. Formaggio F., Crisma M., Toniolo C., Mazaleyrat J.-P., Wakselman M. Bajusz S., Hudecz F. Peptides 1998. 1999;352-353 Akadémiai Kiado, Budapest.
22. Formaggio F., Crisma M., Toniolo C., Tchertanov L., Guilhem J., Mazaleyrat J.P., Gaucher A., Wakselman M. Tetrahedron. 56:2000;8721-8734.
23. Mazaleyrat J.-P., Boutboul A., Lebars Y., Gaucher A., Wakselman M. Tetrahedron: Asymmetry. 9:1998;2701-2713.
24. Formaggio F., Peggion C., Crisma M., Toniolo C., Tchertanov L., Guilhem J., Mazaleyrat J.P., Goubard Y., Gaucher A., Wakselman M. Helv. Chim. Acta. 84:2001;481-501.
25. For reviews on synthesis, molecular recognition, asymmetric catalysis and new materials involving 1,1′-binaphthyl monomers, dimers, oligomers and polymers, see: (a) Cram, D. J. Angew. Chem., Int. Ed. Engl. 1988, 27, 1009-1020; (b) Whitesell, J. K. Chem. Rev. 1989, 89, 1581-1590; (c) Noyori, R.; Takaya, H. Acc. Chem. Res. 1990, 23, 345-350; (d) Rosini, C.; Francini, L.; Raffaelli, A.; Salvadori, P. Synthesis 1992, 503-517; (e) Blaser, H.-U. Chem. Rev. 1992, 92, 935-952; (f) Shibasaki, M.; Sasai, H.; Arai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 1236-1256; (g) Pu, L. Chem. Rev. 1998, 98, 2405-2494; (h) Putala, M. Enantiomer 1999, 4, 243-262.
26. For reviews on synthesis, molecular recognition, asymmetric catalysis and new materials involving 1,1′-binaphthyl monomers, dimers, oligomers and polymers, see: (a) Cram, D. J. Angew. Chem., Int. Ed. Engl. 1988, 27, 1009-1020; (b) Whitesell, J. K. Chem. Rev. 1989, 89, 1581-1590; (c) Noyori, R.; Takaya, H. Acc. Chem. Res. 1990, 23, 345-350; (d) Rosini, C.; Francini, L.; Raffaelli, A.; Salvadori, P. Synthesis 1992, 503-517; (e) Blaser, H.-U. Chem. Rev. 1992, 92, 935-952; (f) Shibasaki, M.; Sasai, H.; Arai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 1236-1256; (g) Pu, L. Chem. Rev. 1998, 98, 2405-2494; (h) Putala, M. Enantiomer 1999, 4, 243-262.
27. For reviews on synthesis, molecular recognition, asymmetric catalysis and new materials involving 1,1′-binaphthyl monomers, dimers, oligomers and polymers, see: (a) Cram, D. J. Angew. Chem., Int. Ed. Engl. 1988, 27, 1009-1020; (b) Whitesell, J. K. Chem. Rev. 1989, 89, 1581-1590; (c) Noyori, R.; Takaya, H. Acc. Chem. Res. 1990, 23, 345-350; (d) Rosini, C.; Francini, L.; Raffaelli, A.; Salvadori, P. Synthesis 1992, 503-517; (e) Blaser, H.-U. Chem. Rev. 1992, 92, 935-952; (f) Shibasaki, M.; Sasai, H.; Arai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 1236-1256; (g) Pu, L. Chem. Rev. 1998, 98, 2405-2494; (h) Putala, M. Enantiomer 1999, 4, 243-262.
28. For reviews on synthesis, molecular recognition, asymmetric catalysis and new materials involving 1,1′-binaphthyl monomers, dimers, oligomers and polymers, see: (a) Cram, D. J. Angew. Chem., Int. Ed. Engl. 1988, 27, 1009-1020; (b) Whitesell, J. K. Chem. Rev. 1989, 89, 1581-1590; (c) Noyori, R.; Takaya, H. Acc. Chem. Res. 1990, 23, 345-350; (d) Rosini, C.; Francini, L.; Raffaelli, A.; Salvadori, P. Synthesis 1992, 503-517; (e) Blaser, H.-U. Chem. Rev. 1992, 92, 935-952; (f) Shibasaki, M.; Sasai, H.; Arai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 1236-1256; (g) Pu, L. Chem. Rev. 1998, 98, 2405-2494; (h) Putala, M. Enantiomer 1999, 4, 243-262.
29. For reviews on synthesis, molecular recognition, asymmetric catalysis and new materials involving 1,1′-binaphthyl monomers, dimers, oligomers and polymers, see: (a) Cram, D. J. Angew. Chem., Int. Ed. Engl. 1988, 27, 1009-1020; (b) Whitesell, J. K. Chem. Rev. 1989, 89, 1581-1590; (c) Noyori, R.; Takaya, H. Acc. Chem. Res. 1990, 23, 345-350; (d) Rosini, C.; Francini, L.; Raffaelli, A.; Salvadori, P. Synthesis 1992, 503-517; (e) Blaser, H.-U. Chem. Rev. 1992, 92, 935-952; (f) Shibasaki, M.; Sasai, H.; Arai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 1236-1256; (g) Pu, L. Chem. Rev. 1998, 98, 2405-2494; (h) Putala, M. Enantiomer 1999, 4, 243-262.
30. For reviews on synthesis, molecular recognition, asymmetric catalysis and new materials involving 1,1′-binaphthyl monomers, dimers, oligomers and polymers, see: (a) Cram, D. J. Angew. Chem., Int. Ed. Engl. 1988, 27, 1009-1020; (b) Whitesell, J. K. Chem. Rev. 1989, 89, 1581-1590; (c) Noyori, R.; Takaya, H. Acc. Chem. Res. 1990, 23, 345-350; (d) Rosini, C.; Francini, L.; Raffaelli, A.; Salvadori, P. Synthesis 1992, 503-517; (e) Blaser, H.-U. Chem. Rev. 1992, 92, 935-952; (f) Shibasaki, M.; Sasai, H.; Arai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 1236-1256; (g) Pu, L. Chem. Rev. 1998, 98, 2405-2494; (h) Putala, M. Enantiomer 1999, 4, 243-262.
31. For reviews on synthesis, molecular recognition, asymmetric catalysis and new materials involving 1,1′-binaphthyl monomers, dimers, oligomers and polymers, see: (a) Cram, D. J. Angew. Chem., Int. Ed. Engl. 1988, 27, 1009-1020; (b) Whitesell, J. K. Chem. Rev. 1989, 89, 1581-1590; (c) Noyori, R.; Takaya, H. Acc. Chem. Res. 1990, 23, 345-350; (d) Rosini, C.; Francini, L.; Raffaelli, A.; Salvadori, P. Synthesis 1992, 503-517; (e) Blaser, H.-U. Chem. Rev. 1992, 92, 935-952; (f) Shibasaki, M.; Sasai, H.; Arai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 1236-1256; (g) Pu, L. Chem. Rev. 1998, 98, 2405-2494; (h) Putala, M. Enantiomer 1999, 4, 243-262.
32. For reviews on synthesis, molecular recognition, asymmetric catalysis and new materials involving 1,1′-binaphthyl monomers, dimers, oligomers and polymers, see: (a) Cram, D. J. Angew. Chem., Int. Ed. Engl. 1988, 27, 1009-1020; (b) Whitesell, J. K. Chem. Rev. 1989, 89, 1581-1590; (c) Noyori, R.; Takaya, H. Acc. Chem. Res. 1990, 23, 345-350; (d) Rosini, C.; Francini, L.; Raffaelli, A.; Salvadori, P. Synthesis 1992, 503-517; (e) Blaser, H.-U. Chem. Rev. 1992, 92, 935-952; (f) Shibasaki, M.; Sasai, H.; Arai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 1236-1256; (g) Pu, L. Chem. Rev. 1998, 98, 2405-2494; (h) Putala, M. Enantiomer 1999, 4, 243-262.
33. The Bin residue has been used as fluorophore in photophysical studies involving intramolecular energy transfer (fluorescence quenching) and intramolecular spin polarisation (CIDEP) effects in designed, rigid peptide-based systems: (a) Toniolo, C.; Formaggio, F.; Crisma, M.; Mazaleyrat, J. P.; Wakselman, M.; George, C.; Deschamps, J. R.; Flippen-Anderson, J. L.; Pispisa, B.; Venanzi, M.; Palleschi, A. Chem. Eur. J. 1999, 5, 2254-2264; (b) Corvaja, C.; Sartori, E.; Toffoletti, A.; Formaggio, F.; Crisma, M.; Toniolo, C.; Mazaleyrat, J. P.; Wakselman, M. Chem. Eur. J. 2000, 6, 2775-2782.
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