A practical synthesis of peptide mimetics via the solid-phase Petasis reaction

Tetrahedron Letters

Volumn 41, Issue 25, 2000, Pages 4835-4839

  Klopfenstein, Sean R ^a   Chen, Jack J ^a   Golebiowski, Adam ^a   Li, Min ^a   Peng, Sean X ^a   Shao, Xia ^a  

^a PROCTER AND GAMBLE PHARMACEUTICALS   (United States)

Author keywords

Boronic acid; Combinatorial chemistry; Glyoxylic acid; Mannich reaction; Solid phase synthesis

Indexed keywords

PEPTIDE DERIVATIVE;

ARTICLE; CHEMICAL BOND; ORGANIC CHEMISTRY; PEPTIDE SYNTHESIS; PROTEIN STRUCTURE; REACTION ANALYSIS;

EID: 0034686193     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00668-7     Document Type: Article

References (30)

1. For reviews, see: (a) Hanessian, S.; McNaughton-Smith, G.; Lombart, H. G.; Lubell, W. D. Tetrahedron 1997, 53, 12789. (b) Olson, G. L.; Cicariello, J.; Gillespie, P. Biopolymer 1997, 43, 191. (c) Hruby, V. J.; Li, G.; Haskell-Luevano, C.; Shenderovich, M. Biopoly. 1997, 43, 219. (d) Goodman, M.; Ro, S. In Burgers Medicinal Chemistry and Drug Discovery, 5th ed.; Wolff, M. E., Ed.; John Wiley & Sons: New York, 1995; Vol. 1. pp. 803861. (e) Giannis, A.; Kolter, T. Angew. Chem., Int. Ed. Engl. 1993, 32, 1244. (f) Jung, G.; Beck-Sickinger, A. G. Angew. Chem., Int. Ed. Engl. 1992, 31, 367. (g) Hruby, V. J. Peptides Chemistry: Structure and Biology; Hudges, R. S.; Smith, J. A., Eds. Proceedings of the Thirteenth American Peptide Symposium. Escom Science Publishers B.V.: Leiden, 1993; pp. 317. (h) Simon, R. J.; Kania, R. S.; Zuckerman, R. N.; Huebner, V. D.; Jewell, D. A.; Banville, S. C.; Ng, S.; Wang, L.; Rosenberg, S.; Marlowe, C. K.; Spellmeyer, D.; Tan, R.; Frankel, A. D.; Santi, D. V.; Cohen, F. E.; Bartlett, P. A. Proc. Natl. Acad. Sci. USA 1992, 89, 9367. (i) Zuckerman, R. N.; Kerr, J. M.; Kent, S. B. H.; Moos, W. H. J. Am. Chem. Soc. 1992, 114, 10646.
2. For reviews, see: (a) Hanessian, S.; McNaughton-Smith, G.; Lombart, H. G.; Lubell, W. D. Tetrahedron 1997, 53, 12789. (b) Olson, G. L.; Cicariello, J.; Gillespie, P. Biopolymer 1997, 43, 191. (c) Hruby, V. J.; Li, G.; Haskell-Luevano, C.; Shenderovich, M. Biopoly. 1997, 43, 219. (d) Goodman, M.; Ro, S. In Burgers Medicinal Chemistry and Drug Discovery, 5th ed.; Wolff, M. E., Ed.; John Wiley & Sons: New York, 1995; Vol. 1. pp. 803861. (e) Giannis, A.; Kolter, T. Angew. Chem., Int. Ed. Engl. 1993, 32, 1244. (f) Jung, G.; Beck-Sickinger, A. G. Angew. Chem., Int. Ed. Engl. 1992, 31, 367. (g) Hruby, V. J. Peptides Chemistry: Structure and Biology; Hudges, R. S.; Smith, J. A., Eds. Proceedings of the Thirteenth American Peptide Symposium. Escom Science Publishers B.V.: Leiden, 1993; pp. 317. (h) Simon, R. J.; Kania, R. S.; Zuckerman, R. N.; Huebner, V. D.; Jewell, D. A.; Banville, S. C.; Ng, S.; Wang, L.; Rosenberg, S.; Marlowe, C. K.; Spellmeyer, D.; Tan, R.; Frankel, A. D.; Santi, D. V.; Cohen, F. E.; Bartlett, P. A. Proc. Natl. Acad. Sci. USA 1992, 89, 9367. (i) Zuckerman, R. N.; Kerr, J. M.; Kent, S. B. H.; Moos, W. H. J. Am. Chem. Soc. 1992, 114, 10646.
3. For reviews, see: (a) Hanessian, S.; McNaughton-Smith, G.; Lombart, H. G.; Lubell, W. D. Tetrahedron 1997, 53, 12789. (b) Olson, G. L.; Cicariello, J.; Gillespie, P. Biopolymer 1997, 43, 191. (c) Hruby, V. J.; Li, G.; Haskell-Luevano, C.; Shenderovich, M. Biopoly. 1997, 43, 219. (d) Goodman, M.; Ro, S. In Burgers Medicinal Chemistry and Drug Discovery, 5th ed.; Wolff, M. E., Ed.; John Wiley & Sons: New York, 1995; Vol. 1. pp. 803861. (e) Giannis, A.; Kolter, T. Angew. Chem., Int. Ed. Engl. 1993, 32, 1244. (f) Jung, G.; Beck-Sickinger, A. G. Angew. Chem., Int. Ed. Engl. 1992, 31, 367. (g) Hruby, V. J. Peptides Chemistry: Structure and Biology; Hudges, R. S.; Smith, J. A., Eds. Proceedings of the Thirteenth American Peptide Symposium. Escom Science Publishers B.V.: Leiden, 1993; pp. 317. (h) Simon, R. J.; Kania, R. S.; Zuckerman, R. N.; Huebner, V. D.; Jewell, D. A.; Banville, S. C.; Ng, S.; Wang, L.; Rosenberg, S.; Marlowe, C. K.; Spellmeyer, D.; Tan, R.; Frankel, A. D.; Santi, D. V.; Cohen, F. E.; Bartlett, P. A. Proc. Natl. Acad. Sci. USA 1992, 89, 9367. (i) Zuckerman, R. N.; Kerr, J. M.; Kent, S. B. H.; Moos, W. H. J. Am. Chem. Soc. 1992, 114, 10646.
4. For reviews, see: (a) Hanessian, S.; McNaughton-Smith, G.; Lombart, H. G.; Lubell, W. D. Tetrahedron 1997, 53, 12789. (b) Olson, G. L.; Cicariello, J.; Gillespie, P. Biopolymer 1997, 43, 191. (c) Hruby, V. J.; Li, G.; Haskell-Luevano, C.; Shenderovich, M. Biopoly. 1997, 43, 219. (d) Goodman, M.; Ro, S. In Burgers Medicinal Chemistry and Drug Discovery, 5th ed.; Wolff, M. E., Ed.; John Wiley & Sons: New York, 1995; Vol. 1. pp. 803861. (e) Giannis, A.; Kolter, T. Angew. Chem., Int. Ed. Engl. 1993, 32, 1244. (f) Jung, G.; Beck-Sickinger, A. G. Angew. Chem., Int. Ed. Engl. 1992, 31, 367. (g) Hruby, V. J. Peptides Chemistry: Structure and Biology; Hudges, R. S.; Smith, J. A., Eds. Proceedings of the Thirteenth American Peptide Symposium. Escom Science Publishers B.V.: Leiden, 1993; pp. 317. (h) Simon, R. J.; Kania, R. S.; Zuckerman, R. N.; Huebner, V. D.; Jewell, D. A.; Banville, S. C.; Ng, S.; Wang, L.; Rosenberg, S.; Marlowe, C. K.; Spellmeyer, D.; Tan, R.; Frankel, A. D.; Santi, D. V.; Cohen, F. E.; Bartlett, P. A. Proc. Natl. Acad. Sci. USA 1992, 89, 9367. (i) Zuckerman, R. N.; Kerr, J. M.; Kent, S. B. H.; Moos, W. H. J. Am. Chem. Soc. 1992, 114, 10646.
5. (e) For reviews, see: (a) Hanessian, S.; McNaughton-Smith, G.; Lombart, H. G.; Lubell, W. D. Tetrahedron 1997, 53, 12789. (b) Olson, G. L.; Cicariello, J.; Gillespie, P. Biopolymer 1997, 43, 191. (c) Hruby, V. J.; Li, G.; Haskell-Luevano, C.; Shenderovich, M. Biopoly. 1997, 43, 219. (d) Goodman, M.; Ro, S. In Burgers Medicinal Chemistry and Drug Discovery, 5th ed.; Wolff, M. E., Ed.; John Wiley & Sons: New York, 1995; Vol. 1. pp. 803861. (e) Giannis, A.; Kolter, T. Angew. Chem., Int. Ed. Engl. 1993, 32, 1244. (f) Jung, G.; Beck-Sickinger, A. G. Angew. Chem., Int. Ed. Engl. 1992, 31, 367. (g) Hruby, V. J. Peptides Chemistry: Structure and Biology; Hudges, R. S.; Smith, J. A., Eds. Proceedings of the Thirteenth American Peptide Symposium. Escom Science Publishers B.V.: Leiden, 1993; pp. 317. (h) Simon, R. J.; Kania, R. S.; Zuckerman, R. N.; Huebner, V. D.; Jewell, D. A.; Banville, S. C.; Ng, S.; Wang, L.; Rosenberg, S.; Marlowe, C. K.; Spellmeyer, D.; Tan, R.; Frankel, A. D.; Santi, D. V.; Cohen, F. E.; Bartlett, P. A. Proc. Natl. Acad. Sci. USA 1992, 89, 9367. (i) Zuckerman, R. N.; Kerr, J. M.; Kent, S. B. H.; Moos, W. H. J. Am. Chem. Soc. 1992, 114, 10646.
6. For reviews, see: (a) Hanessian, S.; McNaughton-Smith, G.; Lombart, H. G.; Lubell, W. D. Tetrahedron 1997, 53, 12789. (b) Olson, G. L.; Cicariello, J.; Gillespie, P. Biopolymer 1997, 43, 191. (c) Hruby, V. J.; Li, G.; Haskell-Luevano, C.; Shenderovich, M. Biopoly. 1997, 43, 219. (d) Goodman, M.; Ro, S. In Burgers Medicinal Chemistry and Drug Discovery, 5th ed.; Wolff, M. E., Ed.; John Wiley & Sons: New York, 1995; Vol. 1. pp. 803861. (e) Giannis, A.; Kolter, T. Angew. Chem., Int. Ed. Engl. 1993, 32, 1244. (f) Jung, G.; Beck-Sickinger, A. G. Angew. Chem., Int. Ed. Engl. 1992, 31, 367. (g) Hruby, V. J. Peptides Chemistry: Structure and Biology; Hudges, R. S.; Smith, J. A., Eds. Proceedings of the Thirteenth American Peptide Symposium. Escom Science Publishers B.V.: Leiden, 1993; pp. 317. (h) Simon, R. J.; Kania, R. S.; Zuckerman, R. N.; Huebner, V. D.; Jewell, D. A.; Banville, S. C.; Ng, S.; Wang, L.; Rosenberg, S.; Marlowe, C. K.; Spellmeyer, D.; Tan, R.; Frankel, A. D.; Santi, D. V.; Cohen, F. E.; Bartlett, P. A. Proc. Natl. Acad. Sci. USA 1992, 89, 9367. (i) Zuckerman, R. N.; Kerr, J. M.; Kent, S. B. H.; Moos, W. H. J. Am. Chem. Soc. 1992, 114, 10646.
7. For reviews, see: (a) Hanessian, S.; McNaughton-Smith, G.; Lombart, H. G.; Lubell, W. D. Tetrahedron 1997, 53, 12789. (b) Olson, G. L.; Cicariello, J.; Gillespie, P. Biopolymer 1997, 43, 191. (c) Hruby, V. J.; Li, G.; Haskell-Luevano, C.; Shenderovich, M. Biopoly. 1997, 43, 219. (d) Goodman, M.; Ro, S. In Burgers Medicinal Chemistry and Drug Discovery, 5th ed.; Wolff, M. E., Ed.; John Wiley & Sons: New York, 1995; Vol. 1. pp. 803861. (e) Giannis, A.; Kolter, T. Angew. Chem., Int. Ed. Engl. 1993, 32, 1244. (f) Jung, G.; Beck-Sickinger, A. G. Angew. Chem., Int. Ed. Engl. 1992, 31, 367. (g) Hruby, V. J. Peptides Chemistry: Structure and Biology; Hudges, R. S.; Smith, J. A., Eds. Proceedings of the Thirteenth American Peptide Symposium. Escom Science Publishers B.V.: Leiden, 1993; pp. 317. (h) Simon, R. J.; Kania, R. S.; Zuckerman, R. N.; Huebner, V. D.; Jewell, D. A.; Banville, S. C.; Ng, S.; Wang, L.; Rosenberg, S.; Marlowe, C. K.; Spellmeyer, D.; Tan, R.; Frankel, A. D.; Santi, D. V.; Cohen, F. E.; Bartlett, P. A. Proc. Natl. Acad. Sci. USA 1992, 89, 9367. (i) Zuckerman, R. N.; Kerr, J. M.; Kent, S. B. H.; Moos, W. H. J. Am. Chem. Soc. 1992, 114, 10646.
8. For reviews, see: (a) Hanessian, S.; McNaughton-Smith, G.; Lombart, H. G.; Lubell, W. D. Tetrahedron 1997, 53, 12789. (b) Olson, G. L.; Cicariello, J.; Gillespie, P. Biopolymer 1997, 43, 191. (c) Hruby, V. J.; Li, G.; Haskell-Luevano, C.; Shenderovich, M. Biopoly. 1997, 43, 219. (d) Goodman, M.; Ro, S. In Burgers Medicinal Chemistry and Drug Discovery, 5th ed.; Wolff, M. E., Ed.; John Wiley & Sons: New York, 1995; Vol. 1. pp. 803861. (e) Giannis, A.; Kolter, T. Angew. Chem., Int. Ed. Engl. 1993, 32, 1244. (f) Jung, G.; Beck-Sickinger, A. G. Angew. Chem., Int. Ed. Engl. 1992, 31, 367. (g) Hruby, V. J. Peptides Chemistry: Structure and Biology; Hudges, R. S.; Smith, J. A., Eds. Proceedings of the Thirteenth American Peptide Symposium. Escom Science Publishers B.V.: Leiden, 1993; pp. 317. (h) Simon, R. J.; Kania, R. S.; Zuckerman, R. N.; Huebner, V. D.; Jewell, D. A.; Banville, S. C.; Ng, S.; Wang, L.; Rosenberg, S.; Marlowe, C. K.; Spellmeyer, D.; Tan, R.; Frankel, A. D.; Santi, D. V.; Cohen, F. E.; Bartlett, P. A. Proc. Natl. Acad. Sci. USA 1992, 89, 9367. (i) Zuckerman, R. N.; Kerr, J. M.; Kent, S. B. H.; Moos, W. H. J. Am. Chem. Soc. 1992, 114, 10646.
9. For reviews, see: (a) Hanessian, S.; McNaughton-Smith, G.; Lombart, H. G.; Lubell, W. D. Tetrahedron 1997, 53, 12789. (b) Olson, G. L.; Cicariello, J.; Gillespie, P. Biopolymer 1997, 43, 191. (c) Hruby, V. J.; Li, G.; Haskell-Luevano, C.; Shenderovich, M. Biopoly. 1997, 43, 219. (d) Goodman, M.; Ro, S. In Burgers Medicinal Chemistry and Drug Discovery, 5th ed.; Wolff, M. E., Ed.; John Wiley & Sons: New York, 1995; Vol. 1. pp. 803861. (e) Giannis, A.; Kolter, T. Angew. Chem., Int. Ed. Engl. 1993, 32, 1244. (f) Jung, G.; Beck-Sickinger, A. G. Angew. Chem., Int. Ed. Engl. 1992, 31, 367. (g) Hruby, V. J. Peptides Chemistry: Structure and Biology; Hudges, R. S.; Smith, J. A., Eds. Proceedings of the Thirteenth American Peptide Symposium. Escom Science Publishers B.V.: Leiden, 1993; pp. 317. (h) Simon, R. J.; Kania, R. S.; Zuckerman, R. N.; Huebner, V. D.; Jewell, D. A.; Banville, S. C.; Ng, S.; Wang, L.; Rosenberg, S.; Marlowe, C. K.; Spellmeyer, D.; Tan, R.; Frankel, A. D.; Santi, D. V.; Cohen, F. E.; Bartlett, P. A. Proc. Natl. Acad. Sci. USA 1992, 89, 9367. (i) Zuckerman, R. N.; Kerr, J. M.; Kent, S. B. H.; Moos, W. H. J. Am. Chem. Soc. 1992, 114, 10646.
10. For reviews, see: (a) Armstrong, R.; Brown, D.; Keating, T.; Tempest, P. In Combinatorial Chemistry Synthesis and Applications; Czarnik, A., Wilson, S., Eds.; John Wiley & Sons: New York, 1997; p. 153. (b) Posner, G. Chem. Rev. 1986, 86, 831. (c) Ugi, I.; Lohberger, R. K. In Comprehensive Organic Synthesis; Trost, B.; Fleming, I., Eds.; Pergamon: New York, 1991; Vol. 2, pp. 10831109. (d) Ugi, I.; Domling, W. H. Endeavor, 1994, 18, 115.
11. For reviews, see: (a) Armstrong, R.; Brown, D.; Keating, T.; Tempest, P. In Combinatorial Chemistry Synthesis and Applications; Czarnik, A., Wilson, S., Eds.; John Wiley & Sons: New York, 1997; p. 153. (b) Posner, G. Chem. Rev. 1986, 86, 831. (c) Ugi, I.; Lohberger, R. K. In Comprehensive Organic Synthesis; Trost, B.; Fleming, I., Eds.; Pergamon: New York, 1991; Vol. 2, pp. 10831109. (d) Ugi, I.; Domling, W. H. Endeavor, 1994, 18, 115.
12. For reviews, see: (a) Armstrong, R.; Brown, D.; Keating, T.; Tempest, P. In Combinatorial Chemistry Synthesis and Applications; Czarnik, A., Wilson, S., Eds.; John Wiley & Sons: New York, 1997; p. 153. (b) Posner, G. Chem. Rev. 1986, 86, 831. (c) Ugi, I.; Lohberger, R. K. In Comprehensive Organic Synthesis; Trost, B.; Fleming, I., Eds.; Pergamon: New York, 1991; Vol. 2, pp. 10831109. (d) Ugi, I.; Domling, W. H. Endeavor, 1994, 18, 115.
13. For reviews, see: (a) Armstrong, R.; Brown, D.; Keating, T.; Tempest, P. In Combinatorial Chemistry Synthesis and Applications; Czarnik, A., Wilson, S., Eds.; John Wiley & Sons: New York, 1997; p. 153. (b) Posner, G. Chem. Rev. 1986, 86, 831. (c) Ugi, I.; Lohberger, R. K. In Comprehensive Organic Synthesis; Trost, B.; Fleming, I., Eds.; Pergamon: New York, 1991; Vol. 2, pp. 10831109. (d) Ugi, I.; Domling, W. H. Endeavor, 1994, 18, 115.
14. (a) Petasis, N. A.; Akritopoulou, I. Tetrahedron Lett. 1993, 34, 583.
15. (b) Petasis, N. A.; Zavialov, I. A. J. Am. Chem. Soc. 1997, 119, 445.
16. (c) Petasis, N. A.; Goodman, A.; Zavialov, I. A. Tetrahedron 1997, 53, 16463.
17. (d) Petasis, N. A.; Zavialov, I. A. J. Am. Chem. Soc. 1998, 120, 11798.
18. (e) Hansen, T. K.; Schlienger, N.; Hansen, B. S.; Anderson, P. H.; Bryce, M. R. Tetrahedron Lett. 1999, 40, 3651.
19. (f) Harwood, L. M.; Currie, G. S.; Drew, G. B.; Luke, R. W. A. Chem. Commun. 1996, 1953.
20. Another approach is the use of a convertible isocyanide: (a) Armstrong, R. W.; Keating, T. A. J. Amer. Chem. Soc. 1995, 117, 7842. (b) Armstrong, R. W.; Keating, T. A. J. Amer. Chem. Soc. 1996, 118, 2574. (c) Armstrong, R. W.; Strocker, A. M.; Keating, T. A.; Tempest, P. A. Tetrahedron Lett. 1996, 37, 1149.
21. Another approach is the use of a convertible isocyanide: (a) Armstrong, R. W.; Keating, T. A. J. Amer. Chem. Soc. 1995, 117, 7842. (b) Armstrong, R. W.; Keating, T. A. J. Amer. Chem. Soc. 1996, 118, 2574. (c) Armstrong, R. W.; Strocker, A. M.; Keating, T. A.; Tempest, P. A. Tetrahedron Lett. 1996, 37, 1149.
22. Another approach is the use of a convertible isocyanide: (a) Armstrong, R. W.; Keating, T. A. J. Amer. Chem. Soc. 1995, 117, 7842. (b) Armstrong, R. W.; Keating, T. A. J. Amer. Chem. Soc. 1996, 118, 2574. (c) Armstrong, R. W.; Strocker, A. M.; Keating, T. A.; Tempest, P. A. Tetrahedron Lett. 1996, 37, 1149.
23. White, P. D.; Chan, W. C. In Fmoc Solid Phase Peptide Synthesis; Chan,W. C.; White, P. D., Eds.; Oxford University Press: New York, 2000; pp. 27-30.
24. (a) Look, G. C.; Murphy, M. M.; Campbell, D. A.; Gallop, M. A. Tetrahedron Lett. 1995, 36, 2937.
25. (b) Campbell, D. A.; Szardenings, A. K.; Burkoth, T. S.; Look, G. C. J.Org. Chem. 1996, 61, 6720.
26. The mechanism of this reaction has not been fully elaborated. For a brief discussion see Ref 3a.
27. In most cases diastereomers could be separated by reverse-phase HPLC and rarely showed greater than 1:1 selectivity. One possible explanation for this is that the amines in the above examples did not contain the (S)-2-phenylglycinol substitution demonstrated by Petasis to increase diastereomeric ratios (see Ref. 3b).
28. Column: Chiralcel OD-R, 4.6×150 mm; mobile phase: 78% methanol:22% water:0.1% formic acid (v/v/v); flow rate: 1 mL/min; UV detection at 210 nm.
29. The configurationally labile intermediate in the Petasis sequence may be the imino ester. Related imino acid analogs have been shown to be configurationally labile under acid. See Lubell, W. D., et al. J. Org. Chem. 1996, 61, 9447.
30. Products analyzed for purity by LC/MS with ELSD and UV detection at 220 nm.