A new and versatile procedure for the incorporation of α,β-diamino acids into peptides

Chemical Communications

Volumn , Issue 5, 1996, Pages 633-634

  Palomo, Claudio ^a   Aizpurua, Jesus M ^a   Galarza, Regina ^a   Mielgo, Antonia ^a  

^a UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; BETA LACTAM DERIVATIVE; DIAMINO ACID; ESTER; PEPTIDE; POTASSIUM CYANIDE; SODIUM AZIDE;

ARTICLE; PEPTIDE SYNTHESIS;

EID: 0029877120     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/CC9960000633     Document Type: Article

References (39)

1. W. F. DeGrado, Adv. Protein. Chem., 1988, 39, 51; A. Giannis and T. Kolter, Angew. Chem., Int. Ed. Engl., 1993, 32, 1244; J. Gante. Angew. Chem., Int. Ed. Engl., 1994, 33, 1699.
2. W. F. DeGrado, Adv. Protein. Chem., 1988, 39, 51; A. Giannis and T. Kolter, Angew. Chem., Int. Ed. Engl., 1993, 32, 1244; J. Gante. Angew. Chem., Int. Ed. Engl., 1994, 33, 1699.
3. W. F. DeGrado, Adv. Protein. Chem., 1988, 39, 51; A. Giannis and T. Kolter, Angew. Chem., Int. Ed. Engl., 1993, 32, 1244; J. Gante. Angew. Chem., Int. Ed. Engl., 1994, 33, 1699.
4. For general reviews on α-amino acids, see: G. M. Coppola and H. F. Schuster, in Asymmetric Synthesis, Construction of Chiral Molecules Using Amino Acids, John Wiley, New York, 1987; R. M. Williams, Synthesis of Optically Active Amino Acids, Pergamon Press, Oxford. 1989; R. O. Duthaler, Tetrahedron. 1994, 50, 1539: For general reviews on β-amino acids, see C. N. C. Drey, in Chemistry and Biochemistry of Amino Acids, ed. G. C. Barrett, Chapman and Hall, London, 1985, p. 25; E. Juaristi, D. Quintana and J. Escalante, Aldrichimica Actat, 1994, 27, 3; D. C. Cole, Tetrahedron, 1994, 50, 9517.
5. For general reviews on α-amino acids, see: G. M. Coppola and H. F. Schuster, in Asymmetric Synthesis, Construction of Chiral Molecules Using Amino Acids, John Wiley, New York, 1987; R. M. Williams, Synthesis of Optically Active Amino Acids, Pergamon Press, Oxford. 1989; R. O. Duthaler, Tetrahedron. 1994, 50, 1539: For general reviews on β-amino acids, see C. N. C. Drey, in Chemistry and Biochemistry of Amino Acids, ed. G. C. Barrett, Chapman and Hall, London, 1985, p. 25; E. Juaristi, D. Quintana and J. Escalante, Aldrichimica Actat, 1994, 27, 3; D. C. Cole, Tetrahedron, 1994, 50, 9517.
6. For general reviews on α-amino acids, see: G. M. Coppola and H. F. Schuster, in Asymmetric Synthesis, Construction of Chiral Molecules Using Amino Acids, John Wiley, New York, 1987; R. M. Williams, Synthesis of Optically Active Amino Acids, Pergamon Press, Oxford. 1989; R. O. Duthaler, Tetrahedron. 1994, 50, 1539: For general reviews on β-amino acids, see C. N. C. Drey, in Chemistry and Biochemistry of Amino Acids, ed. G. C. Barrett, Chapman and Hall, London, 1985, p. 25; E. Juaristi, D. Quintana and J. Escalante, Aldrichimica Actat, 1994, 27, 3; D. C. Cole, Tetrahedron, 1994, 50, 9517.
7. For general reviews on α-amino acids, see: G. M. Coppola and H. F. Schuster, in Asymmetric Synthesis, Construction of Chiral Molecules Using Amino Acids, John Wiley, New York, 1987; R. M. Williams, Synthesis of Optically Active Amino Acids, Pergamon Press, Oxford. 1989; R. O. Duthaler, Tetrahedron. 1994, 50, 1539: For general reviews on β-amino acids, see C. N. C. Drey, in Chemistry and Biochemistry of Amino Acids, ed. G. C. Barrett, Chapman and Hall, London, 1985, p. 25; E. Juaristi, D. Quintana and J. Escalante, Aldrichimica Actat, 1994, 27, 3; D. C. Cole, Tetrahedron, 1994, 50, 9517.
8. For general reviews on α-amino acids, see: G. M. Coppola and H. F. Schuster, in Asymmetric Synthesis, Construction of Chiral Molecules Using Amino Acids, John Wiley, New York, 1987; R. M. Williams, Synthesis of Optically Active Amino Acids, Pergamon Press, Oxford. 1989; R. O. Duthaler, Tetrahedron. 1994, 50, 1539: For general reviews on β-amino acids, see C. N. C. Drey, in Chemistry and Biochemistry of Amino Acids, ed. G. C. Barrett, Chapman and Hall, London, 1985, p. 25; E. Juaristi, D. Quintana and J. Escalante, Aldrichimica Actat, 1994, 27, 3; D. C. Cole, Tetrahedron, 1994, 50, 9517.
9. For general reviews on α-amino acids, see: G. M. Coppola and H. F. Schuster, in Asymmetric Synthesis, Construction of Chiral Molecules Using Amino Acids, John Wiley, New York, 1987; R. M. Williams, Synthesis of Optically Active Amino Acids, Pergamon Press, Oxford. 1989; R. O. Duthaler, Tetrahedron. 1994, 50, 1539: For general reviews on β-amino acids, see C. N. C. Drey, in Chemistry and Biochemistry of Amino Acids, ed. G. C. Barrett, Chapman and Hall, London, 1985, p. 25; E. Juaristi, D. Quintana and J. Escalante, Aldrichimica Actat, 1994, 27, 3; D. C. Cole, Tetrahedron, 1994, 50, 9517.
10. For some recent examples on the synthesis and peptide derivatives of β-amino alanines: D. Seebach, A. Studer, E. Pfmmatter and H. Widmer, Helv. Chim. Acta. 1994, 77, 2035; R. C. F. Jones and G. J. Ward, Tetrahedron Lett., 1988, 29, 3853; I. Gilbert, D. C. Rees and R. S. Richardson, Tetrahedron Lett., 1991, 32, 2277; R. C. F. Jones, A. K. Crockett, D. C. Rees and I. H. Gilbert, Tetrahedron: Asymmetry, 1994, 5, 1661; Tetrahedron, 1995, 51, 6315; P. J. Dunn, R. Häner and H. Rapoport, J. Org. Chem., 1990, 55, 5017; W. Hartwig and J. Mittendorf, Synthesis, 1991, 939; M. E. Solomon, C. L. Lynch and D. H. Rich, Tetrahedron Lett., 1995, 36, 4955; M. Pérez and R. Pleixats, Tetrahedron, 1995, 51, 8355; P. Davoli, A. Forni, I. Moretti and F. Prati, Tetrahedron: Asymmetry, 1995, 6, 2011.
11. For some recent examples on the synthesis and peptide derivatives of β-amino alanines: D. Seebach, A. Studer, E. Pfmmatter and H. Widmer, Helv. Chim. Acta. 1994, 77, 2035; R. C. F. Jones and G. J. Ward, Tetrahedron Lett., 1988, 29, 3853; I. Gilbert, D. C. Rees and R. S. Richardson, Tetrahedron Lett., 1991, 32, 2277; R. C. F. Jones, A. K. Crockett, D. C. Rees and I. H. Gilbert, Tetrahedron: Asymmetry, 1994, 5, 1661; Tetrahedron, 1995, 51, 6315; P. J. Dunn, R. Häner and H. Rapoport, J. Org. Chem., 1990, 55, 5017; W. Hartwig and J. Mittendorf, Synthesis, 1991, 939; M. E. Solomon, C. L. Lynch and D. H. Rich, Tetrahedron Lett., 1995, 36, 4955; M. Pérez and R. Pleixats, Tetrahedron, 1995, 51, 8355; P. Davoli, A. Forni, I. Moretti and F. Prati, Tetrahedron: Asymmetry, 1995, 6, 2011.
12. For some recent examples on the synthesis and peptide derivatives of β-amino alanines: D. Seebach, A. Studer, E. Pfmmatter and H. Widmer, Helv. Chim. Acta. 1994, 77, 2035; R. C. F. Jones and G. J. Ward, Tetrahedron Lett., 1988, 29, 3853; I. Gilbert, D. C. Rees and R. S. Richardson, Tetrahedron Lett., 1991, 32, 2277; R. C. F. Jones, A. K. Crockett, D. C. Rees and I. H. Gilbert, Tetrahedron: Asymmetry, 1994, 5, 1661; Tetrahedron, 1995, 51, 6315; P. J. Dunn, R. Häner and H. Rapoport, J. Org. Chem., 1990, 55, 5017; W. Hartwig and J. Mittendorf, Synthesis, 1991, 939; M. E. Solomon, C. L. Lynch and D. H. Rich, Tetrahedron Lett., 1995, 36, 4955; M. Pérez and R. Pleixats, Tetrahedron, 1995, 51, 8355; P. Davoli, A. Forni, I. Moretti and F. Prati, Tetrahedron: Asymmetry, 1995, 6, 2011.
13. For some recent examples on the synthesis and peptide derivatives of β-amino alanines: D. Seebach, A. Studer, E. Pfmmatter and H. Widmer, Helv. Chim. Acta. 1994, 77, 2035; R. C. F. Jones and G. J. Ward, Tetrahedron Lett., 1988, 29, 3853; I. Gilbert, D. C. Rees and R. S. Richardson, Tetrahedron Lett., 1991, 32, 2277; R. C. F. Jones, A. K. Crockett, D. C. Rees and I. H. Gilbert, Tetrahedron: Asymmetry, 1994, 5, 1661; Tetrahedron, 1995, 51, 6315; P. J. Dunn, R. Häner and H. Rapoport, J. Org. Chem., 1990, 55, 5017; W. Hartwig and J. Mittendorf, Synthesis, 1991, 939; M. E. Solomon, C. L. Lynch and D. H. Rich, Tetrahedron Lett., 1995, 36, 4955; M. Pérez and R. Pleixats, Tetrahedron, 1995, 51, 8355; P. Davoli, A. Forni, I. Moretti and F. Prati, Tetrahedron: Asymmetry, 1995, 6, 2011.
14. For some recent examples on the synthesis and peptide derivatives of β-amino alanines: D. Seebach, A. Studer, E. Pfmmatter and H. Widmer, Helv. Chim. Acta. 1994, 77, 2035; R. C. F. Jones and G. J. Ward, Tetrahedron Lett., 1988, 29, 3853; I. Gilbert, D. C. Rees and R. S. Richardson, Tetrahedron Lett., 1991, 32, 2277; R. C. F. Jones, A. K. Crockett, D. C. Rees and I. H. Gilbert, Tetrahedron: Asymmetry, 1994, 5, 1661; Tetrahedron, 1995, 51, 6315; P. J. Dunn, R. Häner and H. Rapoport, J. Org. Chem., 1990, 55, 5017; W. Hartwig and J. Mittendorf, Synthesis, 1991, 939; M. E. Solomon, C. L. Lynch and D. H. Rich, Tetrahedron Lett., 1995, 36, 4955; M. Pérez and R. Pleixats, Tetrahedron, 1995, 51, 8355; P. Davoli, A. Forni, I. Moretti and F. Prati, Tetrahedron: Asymmetry, 1995, 6, 2011.
15. For some recent examples on the synthesis and peptide derivatives of β-amino alanines: D. Seebach, A. Studer, E. Pfmmatter and H. Widmer, Helv. Chim. Acta. 1994, 77, 2035; R. C. F. Jones and G. J. Ward, Tetrahedron Lett., 1988, 29, 3853; I. Gilbert, D. C. Rees and R. S. Richardson, Tetrahedron Lett., 1991, 32, 2277; R. C. F. Jones, A. K. Crockett, D. C. Rees and I. H. Gilbert, Tetrahedron: Asymmetry, 1994, 5, 1661; Tetrahedron, 1995, 51, 6315; P. J. Dunn, R. Häner and H. Rapoport, J. Org. Chem., 1990, 55, 5017; W. Hartwig and J. Mittendorf, Synthesis, 1991, 939; M. E. Solomon, C. L. Lynch and D. H. Rich, Tetrahedron Lett., 1995, 36, 4955; M. Pérez and R. Pleixats, Tetrahedron, 1995, 51, 8355; P. Davoli, A. Forni, I. Moretti and F. Prati, Tetrahedron: Asymmetry, 1995, 6, 2011.
16. For some recent examples on the synthesis and peptide derivatives of β-amino alanines: D. Seebach, A. Studer, E. Pfmmatter and H. Widmer, Helv. Chim. Acta. 1994, 77, 2035; R. C. F. Jones and G. J. Ward, Tetrahedron Lett., 1988, 29, 3853; I. Gilbert, D. C. Rees and R. S. Richardson, Tetrahedron Lett., 1991, 32, 2277; R. C. F. Jones, A. K. Crockett, D. C. Rees and I. H. Gilbert, Tetrahedron: Asymmetry, 1994, 5, 1661; Tetrahedron, 1995, 51, 6315; P. J. Dunn, R. Häner and H. Rapoport, J. Org. Chem., 1990, 55, 5017; W. Hartwig and J. Mittendorf, Synthesis, 1991, 939; M. E. Solomon, C. L. Lynch and D. H. Rich, Tetrahedron Lett., 1995, 36, 4955; M. Pérez and R. Pleixats, Tetrahedron, 1995, 51, 8355; P. Davoli, A. Forni, I. Moretti and F. Prati, Tetrahedron: Asymmetry, 1995, 6, 2011.
17. For some recent examples on the synthesis and peptide derivatives of β-amino alanines: D. Seebach, A. Studer, E. Pfmmatter and H. Widmer, Helv. Chim. Acta. 1994, 77, 2035; R. C. F. Jones and G. J. Ward, Tetrahedron Lett., 1988, 29, 3853; I. Gilbert, D. C. Rees and R. S. Richardson, Tetrahedron Lett., 1991, 32, 2277; R. C. F. Jones, A. K. Crockett, D. C. Rees and I. H. Gilbert, Tetrahedron: Asymmetry, 1994, 5, 1661; Tetrahedron, 1995, 51, 6315; P. J. Dunn, R. Häner and H. Rapoport, J. Org. Chem., 1990, 55, 5017; W. Hartwig and J. Mittendorf, Synthesis, 1991, 939; M. E. Solomon, C. L. Lynch and D. H. Rich, Tetrahedron Lett., 1995, 36, 4955; M. Pérez and R. Pleixats, Tetrahedron, 1995, 51, 8355; P. Davoli, A. Forni, I. Moretti and F. Prati, Tetrahedron: Asymmetry, 1995, 6, 2011.
18. For some recent examples on the synthesis and peptide derivatives of β-amino alanines: D. Seebach, A. Studer, E. Pfmmatter and H. Widmer, Helv. Chim. Acta. 1994, 77, 2035; R. C. F. Jones and G. J. Ward, Tetrahedron Lett., 1988, 29, 3853; I. Gilbert, D. C. Rees and R. S. Richardson, Tetrahedron Lett., 1991, 32, 2277; R. C. F. Jones, A. K. Crockett, D. C. Rees and I. H. Gilbert, Tetrahedron: Asymmetry, 1994, 5, 1661; Tetrahedron, 1995, 51, 6315; P. J. Dunn, R. Häner and H. Rapoport, J. Org. Chem., 1990, 55, 5017; W. Hartwig and J. Mittendorf, Synthesis, 1991, 939; M. E. Solomon, C. L. Lynch and D. H. Rich, Tetrahedron Lett., 1995, 36, 4955; M. Pérez and R. Pleixats, Tetrahedron, 1995, 51, 8355; P. Davoli, A. Forni, I. Moretti and F. Prati, Tetrahedron: Asymmetry, 1995, 6, 2011.
19. For some recent examples on the synthesis and peptide derivatives of β-amino alanines: D. Seebach, A. Studer, E. Pfmmatter and H. Widmer, Helv. Chim. Acta. 1994, 77, 2035; R. C. F. Jones and G. J. Ward, Tetrahedron Lett., 1988, 29, 3853; I. Gilbert, D. C. Rees and R. S. Richardson, Tetrahedron Lett., 1991, 32, 2277; R. C. F. Jones, A. K. Crockett, D. C. Rees and I. H. Gilbert, Tetrahedron: Asymmetry, 1994, 5, 1661; Tetrahedron, 1995, 51, 6315; P. J. Dunn, R. Häner and H. Rapoport, J. Org. Chem., 1990, 55, 5017; W. Hartwig and J. Mittendorf, Synthesis, 1991, 939; M. E. Solomon, C. L. Lynch and D. H. Rich, Tetrahedron Lett., 1995, 36, 4955; M. Pérez and R. Pleixats, Tetrahedron, 1995, 51, 8355; P. Davoli, A. Forni, I. Moretti and F. Prati, Tetrahedron: Asymmetry, 1995, 6, 2011.
20. J. Mulzer, in Stereoselective Synthesis, ed. E. Ottow, K. Schöllkopf and B. G. Schulz, Springer-Verlag, Berlin, 1993, p. 37.
21. C. Palomo, J. M. Aizpurua and C. Cuevas, J. Chem. Soc., Chem. Commun., 1994, 1957; See also I. Ojima, C. M. Sun and Y. H. Park, J. Org. Chem., 1994, 59, 1249.
22. C. Palomo, J. M. Aizpurua and C. Cuevas, J. Chem. Soc., Chem. Commun., 1994, 1957; See also I. Ojima, C. M. Sun and Y. H. Park, J. Org. Chem., 1994, 59, 1249.
23. For reviews on 3-amino β-lactam synthesis, see J. Backes, in Methoden der Organischen Chemie, ed. E. Muller and O. Bayer, Houben-Weyl, Thieme, Stuttgart, 1991, p. 31; F. H. Van der Steen and G. Van Koten, Tetrahedron, 1991, 47, 7503; G. I. Georg and V. T. Ravikumar, in The Organic Chcmistry of β-Lactams, ed. G. I. Georg, VCH, New York, 1992, p. 295.
24. For reviews on 3-amino β-lactam synthesis, see J. Backes, in Methoden der Organischen Chemie, ed. E. Muller and O. Bayer, Houben-Weyl, Thieme, Stuttgart, 1991, p. 31; F. H. Van der Steen and G. Van Koten, Tetrahedron, 1991, 47, 7503; G. I. Georg and V. T. Ravikumar, in The Organic Chcmistry of β-Lactams, ed. G. I. Georg, VCH, New York, 1992, p. 295.
25. For reviews on 3-amino β-lactam synthesis, see J. Backes, in Methoden der Organischen Chemie, ed. E. Muller and O. Bayer, Houben-Weyl, Thieme, Stuttgart, 1991, p. 31; F. H. Van der Steen and G. Van Koten, Tetrahedron, 1991, 47, 7503; G. I. Georg and V. T. Ravikumar, in The Organic Chcmistry of β-Lactams, ed. G. I. Georg, VCH, New York, 1992, p. 295.
26. For the use of β-lactams in amino acid synthesis, see M. S. Manhas, D. R. Wagle, J. Chiang and A. K. Bose, Heterocycles, 1988, 27, 1755; I. Ojima, in The Organic Chemistry of β-Lactams, ed. G. I. Georg, VCH, New York, 1992, p. 197; I. Ojima, Acc. Chem. Res., 1995, 28, 383; L. S. Hegedus, Acc. Chem. Res., 1995, 28, 299.
27. For the use of β-lactams in amino acid synthesis, see M. S. Manhas, D. R. Wagle, J. Chiang and A. K. Bose, Heterocycles, 1988, 27, 1755; I. Ojima, in The Organic Chemistry of β-Lactams, ed. G. I. Georg, VCH, New York, 1992, p. 197; I. Ojima, Acc. Chem. Res., 1995, 28, 383; L. S. Hegedus, Acc. Chem. Res., 1995, 28, 299.
28. For the use of β-lactams in amino acid synthesis, see M. S. Manhas, D. R. Wagle, J. Chiang and A. K. Bose, Heterocycles, 1988, 27, 1755; I. Ojima, in The Organic Chemistry of β-Lactams, ed. G. I. Georg, VCH, New York, 1992, p. 197; I. Ojima, Acc. Chem. Res., 1995, 28, 383; L. S. Hegedus, Acc. Chem. Res., 1995, 28, 299.
29. For the use of β-lactams in amino acid synthesis, see M. S. Manhas, D. R. Wagle, J. Chiang and A. K. Bose, Heterocycles, 1988, 27, 1755; I. Ojima, in The Organic Chemistry of β-Lactams, ed. G. I. Georg, VCH, New York, 1992, p. 197; I. Ojima, Acc. Chem. Res., 1995, 28, 383; L. S. Hegedus, Acc. Chem. Res., 1995, 28, 299.
30. For a review on enzyme catalysed ring opening of β-lactams, see The Chemistry of β-Lactams, ed. M. I. Page, Blackie, London, 1992.
31. For the use of NaCN to promote ring opening of β-lactams, see F. Cavagna, H. Linkies, H. Petsch and D. Reuschling, Angew. Chem., Int. Ed. Engl., 1980, 19, 129; D. R. Wagle, M. G. Monteleone, L. Krishnan, M. S. Manhas and A. K. Bose, J. Chem. Soc., Chem. Commun., 1989, 8915.
32. For the use of NaCN to promote ring opening of β-lactams, see F. Cavagna, H. Linkies, H. Petsch and D. Reuschling, Angew. Chem., Int. Ed. Engl., 1980, 19, 129; D. R. Wagle, M. G. Monteleone, L. Krishnan, M. S. Manhas and A. K. Bose, J. Chem. Soc., Chem. Commun., 1989, 8915.
33. L. A. Carpino, El-Sayed M. E. Mansour and D. Sadat-Aalaee, J. Org. Chem., 1961, 56, 2611.
34. For some examples on biological target compounds containing α,β-diamino acids, see J. E. Baldwin, R. M. Adlington and D. J. Birch, J. Chem. Soc., Chem. Commun., 1985, 256; Y. Aoyagi, M. S. Chorghade, A. A. Padmapriya, H. Suguna and S. M. Hecht, J. Org. Chem., 1990, 55, 6291; Y. Nakamura and C-gi Shin, Chem. Lett., 1992, 49; R. Herranz, S. Vinuesa, J. Castro-Pichel, C. Pérez and M. T. García-López, J. Chem. Soc., Perkin Trans. 1, 1992, 1825; D. F. Rane, V. M. Girizavallabhan, A. K. Ganguly, R. E. Pike, A. K. Saksena and A. T. McPhail, Tetrahedron Lett., 1993, 34, 3201; M. Wang and S. J. Gould, J. Org. Chem., 1993, 58, 5176.
35. For some examples on biological target compounds containing α,β-diamino acids, see J. E. Baldwin, R. M. Adlington and D. J. Birch, J. Chem. Soc., Chem. Commun., 1985, 256; Y. Aoyagi, M. S. Chorghade, A. A. Padmapriya, H. Suguna and S. M. Hecht, J. Org. Chem., 1990, 55, 6291; Y. Nakamura and C-gi Shin, Chem. Lett., 1992, 49; R. Herranz, S. Vinuesa, J. Castro-Pichel, C. Pérez and M. T. García-López, J. Chem. Soc., Perkin Trans. 1, 1992, 1825; D. F. Rane, V. M. Girizavallabhan, A. K. Ganguly, R. E. Pike, A. K. Saksena and A. T. McPhail, Tetrahedron Lett., 1993, 34, 3201; M. Wang and S. J. Gould, J. Org. Chem., 1993, 58, 5176.
36. For some examples on biological target compounds containing α,β-diamino acids, see J. E. Baldwin, R. M. Adlington and D. J. Birch, J. Chem. Soc., Chem. Commun., 1985, 256; Y. Aoyagi, M. S. Chorghade, A. A. Padmapriya, H. Suguna and S. M. Hecht, J. Org. Chem., 1990, 55, 6291; Y. Nakamura and C-gi Shin, Chem. Lett., 1992, 49; R. Herranz, S. Vinuesa, J. Castro-Pichel, C. Pérez and M. T. García-López, J. Chem. Soc., Perkin Trans. 1, 1992, 1825; D. F. Rane, V. M. Girizavallabhan, A. K. Ganguly, R. E. Pike, A. K. Saksena and A. T. McPhail, Tetrahedron Lett., 1993, 34, 3201; M. Wang and S. J. Gould, J. Org. Chem., 1993, 58, 5176.
37. For some examples on biological target compounds containing α,β-diamino acids, see J. E. Baldwin, R. M. Adlington and D. J. Birch, J. Chem. Soc., Chem. Commun., 1985, 256; Y. Aoyagi, M. S. Chorghade, A. A. Padmapriya, H. Suguna and S. M. Hecht, J. Org. Chem., 1990, 55, 6291; Y. Nakamura and C-gi Shin, Chem. Lett., 1992, 49; R. Herranz, S. Vinuesa, J. Castro-Pichel, C. Pérez and M. T. García-López, J. Chem. Soc., Perkin Trans. 1, 1992, 1825; D. F. Rane, V. M. Girizavallabhan, A. K. Ganguly, R. E. Pike, A. K. Saksena and A. T. McPhail, Tetrahedron Lett., 1993, 34, 3201; M. Wang and S. J. Gould, J. Org. Chem., 1993, 58, 5176.
38. For some examples on biological target compounds containing α,β-diamino acids, see J. E. Baldwin, R. M. Adlington and D. J. Birch, J. Chem. Soc., Chem. Commun., 1985, 256; Y. Aoyagi, M. S. Chorghade, A. A. Padmapriya, H. Suguna and S. M. Hecht, J. Org. Chem., 1990, 55, 6291; Y. Nakamura and C-gi Shin, Chem. Lett., 1992, 49; R. Herranz, S. Vinuesa, J. Castro-Pichel, C. Pérez and M. T. García-López, J. Chem. Soc., Perkin Trans. 1, 1992, 1825; D. F. Rane, V. M. Girizavallabhan, A. K. Ganguly, R. E. Pike, A. K. Saksena and A. T. McPhail, Tetrahedron Lett., 1993, 34, 3201; M. Wang and S. J. Gould, J. Org. Chem., 1993, 58, 5176.
39. For some examples on biological target compounds containing α,β-diamino acids, see J. E. Baldwin, R. M. Adlington and D. J. Birch, J. Chem. Soc., Chem. Commun., 1985, 256; Y. Aoyagi, M. S. Chorghade, A. A. Padmapriya, H. Suguna and S. M. Hecht, J. Org. Chem., 1990, 55, 6291; Y. Nakamura and C-gi Shin, Chem. Lett., 1992, 49; R. Herranz, S. Vinuesa, J. Castro-Pichel, C. Pérez and M. T. García-López, J. Chem. Soc., Perkin Trans. 1, 1992, 1825; D. F. Rane, V. M. Girizavallabhan, A. K. Ganguly, R. E. Pike, A. K. Saksena and A. T. McPhail, Tetrahedron Lett., 1993, 34, 3201; M. Wang and S. J. Gould, J. Org. Chem., 1993, 58, 5176.