Concise synthesis of α-alkyl α-amino acids and their incorporation into peptides via β-lactam-derived α-amino acid N-carboxy anhydrides

Chemical Communications

Volumn , Issue 11, 1996, Pages 1269-1270

  Palomo, Claudio ^a   Aizpurua, J M ^a   Ganboa, Iñaki ^a   Odriozola, Beatriz ^a   Urchegui, Raquel ^a   Görls, Helmar ^b  

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

^b FRIEDRICH SCHILLER UNIVERSITY JENA   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA HYDROXY BETA LACTAM; ALPHA,ALPHA DIALKYL ALPHA AMINO ACID N CARBOXYANHYDRIDE; PEPTIDE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; PROTEIN CONFORMATION; PROTEIN SYNTHESIS; REACTION ANALYSIS;

EID: 0029903149     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/CC9960001269     Document Type: Article

References (28)

1. For comprehensive reviews, see: W. F. Degrado, Adv. Protein Chem., 1988, 39, 51; C. Toniolo, Int. Peptide Protein Res., 1990, 35, 287; A. Giannis and T. Kolter, Angew. Chem., Int. Ed. Engl., 1993, 32, 1244; R. M. J. Liskamp, Recl. Trav. Chim. Pays-Bas, 1994, 113, 1; J. Gante, Angew Chem., Int. Ed. Engl. 1994, 33, 1699.
2. For comprehensive reviews, see: W. F. Degrado, Adv. Protein Chem., 1988, 39, 51; C. Toniolo, Int. Peptide Protein Res., 1990, 35, 287; A. Giannis and T. Kolter, Angew. Chem., Int. Ed. Engl., 1993, 32, 1244; R. M. J. Liskamp, Recl. Trav. Chim. Pays-Bas, 1994, 113, 1; J. Gante, Angew Chem., Int. Ed. Engl. 1994, 33, 1699.
3. For comprehensive reviews, see: W. F. Degrado, Adv. Protein Chem., 1988, 39, 51; C. Toniolo, Int. Peptide Protein Res., 1990, 35, 287; A. Giannis and T. Kolter, Angew. Chem., Int. Ed. Engl., 1993, 32, 1244; R. M. J. Liskamp, Recl. Trav. Chim. Pays-Bas, 1994, 113, 1; J. Gante, Angew Chem., Int. Ed. Engl. 1994, 33, 1699.
4. For comprehensive reviews, see: W. F. Degrado, Adv. Protein Chem., 1988, 39, 51; C. Toniolo, Int. Peptide Protein Res., 1990, 35, 287; A. Giannis and T. Kolter, Angew. Chem., Int. Ed. Engl., 1993, 32, 1244; R. M. J. Liskamp, Recl. Trav. Chim. Pays-Bas, 1994, 113, 1; J. Gante, Angew Chem., Int. Ed. Engl. 1994, 33, 1699.
5. For comprehensive reviews, see: W. F. Degrado, Adv. Protein Chem., 1988, 39, 51; C. Toniolo, Int. Peptide Protein Res., 1990, 35, 287; A. Giannis and T. Kolter, Angew. Chem., Int. Ed. Engl., 1993, 32, 1244; R. M. J. Liskamp, Recl. Trav. Chim. Pays-Bas, 1994, 113, 1; J. Gante, Angew Chem., Int. Ed. Engl. 1994, 33, 1699.
6. For some reviews on α-amino acid synthesis, see R. M. Williams, Synthesis of Optically Active α-Amino Acids, Pergamon: Oxford, 1989; α-Amino Acid Synthesis, ed. H. J. O'Donell, Tetrahedron Symposia-inprint, Tetrahedron, 1988, 44, 5253; R. O. Duthaler, Tetrahedron, 1994, 50, 1539; P. D. Bailey, J. Clayson and A. N. Boa, Contemp. Org. Synth., 1995, 2, 173; L. S. Hegedus, Acc. Chem. Res., 1995, 28, 299.
7. For some reviews on α-amino acid synthesis, see R. M. Williams, Synthesis of Optically Active α-Amino Acids, Pergamon: Oxford, 1989; α-Amino Acid Synthesis, ed. H. J. O'Donell, Tetrahedron Symposia-inprint, Tetrahedron, 1988, 44, 5253; R. O. Duthaler, Tetrahedron, 1994, 50, 1539; P. D. Bailey, J. Clayson and A. N. Boa, Contemp. Org. Synth., 1995, 2, 173; L. S. Hegedus, Acc. Chem. Res., 1995, 28, 299.
8. For some reviews on α-amino acid synthesis, see R. M. Williams, Synthesis of Optically Active α-Amino Acids, Pergamon: Oxford, 1989; α-Amino Acid Synthesis, ed. H. J. O'Donell, Tetrahedron Symposia-inprint, Tetrahedron, 1988, 44, 5253; R. O. Duthaler, Tetrahedron, 1994, 50, 1539; P. D. Bailey, J. Clayson and A. N. Boa, Contemp. Org. Synth., 1995, 2, 173; L. S. Hegedus, Acc. Chem. Res., 1995, 28, 299.
9. For some reviews on α-amino acid synthesis, see R. M. Williams, Synthesis of Optically Active α-Amino Acids, Pergamon: Oxford, 1989; α-Amino Acid Synthesis, ed. H. J. O'Donell, Tetrahedron Symposia-inprint, Tetrahedron, 1988, 44, 5253; R. O. Duthaler, Tetrahedron, 1994, 50, 1539; P. D. Bailey, J. Clayson and A. N. Boa, Contemp. Org. Synth., 1995, 2, 173; L. S. Hegedus, Acc. Chem. Res., 1995, 28, 299.
10. For some reviews on α-amino acid synthesis, see R. M. Williams, Synthesis of Optically Active α-Amino Acids, Pergamon: Oxford, 1989; α-Amino Acid Synthesis, ed. H. J. O'Donell, Tetrahedron Symposia-inprint, Tetrahedron, 1988, 44, 5253; R. O. Duthaler, Tetrahedron, 1994, 50, 1539; P. D. Bailey, J. Clayson and A. N. Boa, Contemp. Org. Synth., 1995, 2, 173; L. S. Hegedus, Acc. Chem. Res., 1995, 28, 299.
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15. For a discussion on this topic, see R. J. Ternansky and J. M. Morin Jr., in The Organic Chemistry of β-Lactams, ed. G. I. Georg, VCH, New York, 1993, p. 257; for a general review on β-lactams see: J. Backes, in Houben-Weyl Methoden der Organischen Chemie, ed. E. Muller and O. Bayer, Band E16B, Thieme, Stuttgart, 1991, p. 31.
16. For a discussion on this topic, see R. J. Ternansky and J. M. Morin Jr., in The Organic Chemistry of β-Lactams, ed. G. I. Georg, VCH, New York, 1993, p. 257; for a general review on β-lactams see: J. Backes, in Houben-Weyl Methoden der Organischen Chemie, ed. E. Muller and O. Bayer, Band E16B, Thieme, Stuttgart, 1991, p. 31.
17. For cycloadditions of glyceraldehide imines, see C. Hubschwerlen and G. Schmid, Helv. Chim. Acta, 1983, 66, 2206; D. R. Wagle, G. Garai, J. Chiang, M. G. Monteleone, B. E. Kurys, T. W. Strohmeyer, V. R. Hedge, M. S. Manhas and A. K. Bose, J. Org. Chem., 1988, 29, 5065.
18. For cycloadditions of glyceraldehide imines, see C. Hubschwerlen and G. Schmid, Helv. Chim. Acta, 1983, 66, 2206; D. R. Wagle, G. Garai, J. Chiang, M. G. Monteleone, B. E. Kurys, T. W. Strohmeyer, V. R. Hedge, M. S. Manhas and A. K. Bose, J. Org. Chem., 1988, 29, 5065.
19. 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.
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21. P. L. Anelli, F. Montanari and S. Quici. Org. Synth. Coll., 1993, 8, 367.
22. J. R. Spencer, V. V. Antonenko, N. G. J. Delaet and M. Goodman, Int. J. Peptide Protein, 1992, 40, 282; for coupling α-branched NCAs with α-amino acid esters, see C. Schierlinger and K. Burger, Tetrahedron Lett., 1992, 33, 193; C. Aurin-Guette, E. Frérot, J. Coste, S. Rebuffat, P. Jouin and B. Bodo, Tetrahedron Lett., 1993, 34, 2481.
23. J. R. Spencer, V. V. Antonenko, N. G. J. Delaet and M. Goodman, Int. J. Peptide Protein, 1992, 40, 282; for coupling α-branched NCAs with α-amino acid esters, see C. Schierlinger and K. Burger, Tetrahedron Lett., 1992, 33, 193; C. Aurin-Guette, E. Frérot, J. Coste, S. Rebuffat, P. Jouin and B. Bodo, Tetrahedron Lett., 1993, 34, 2481.
24. J. R. Spencer, V. V. Antonenko, N. G. J. Delaet and M. Goodman, Int. J. Peptide Protein, 1992, 40, 282; for coupling α-branched NCAs with α-amino acid esters, see C. Schierlinger and K. Burger, Tetrahedron Lett., 1992, 33, 193; C. Aurin-Guette, E. Frérot, J. Coste, S. Rebuffat, P. Jouin and B. Bodo, Tetrahedron Lett., 1993, 34, 2481.
25. For the application of this approach to D-α-methyl-β-alkylserine peptides, see C. Palomo, J. M. Aizpurua, R. Urchegui and J. García, J. Chem. Soc., Chem. Commun., 1995, 2327.
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.
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.
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.