Parallel solid-phase synthesis of partially modified retro and retro-inverso ψ[NHCH(CF3)]-Gly peptides

Collection of Czechoslovak Chemical Communications

Volumn 67, Issue 9, 2002, Pages 1305-1319

  Sani, Monica ^a   Bravo, Pierfrancesco ^a,b   Volonterio, Alessandro ^a   Zanda, Matteo ^a  

^a CNR   (Italy)

^b POLITECNICO DI MILANO   (Italy)

Author keywords

Combinatorial synthesis; Michael reactions; Peptide mimetics; Solid phase synthesis; Trifluoromethyl group

Indexed keywords

3 ENOYL 1,3 OXAZOLIDIN 2 ONE; ALPHA AMINO ACID; ESTER DERIVATIVE; GLYCINE DERIVATIVE; OXAZOLIDINONE DERIVATIVE; PEPTIDE DERIVATIVE; RESIN; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CYCLIZATION; INFRARED SPECTROSCOPY; MICHAEL ADDITION; MOLECULAR DYNAMICS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS;

EID: 0036761499     PISSN: 00100765     EISSN: None     Source Type: Journal    
DOI: 10.1135/cccc20021305     Document Type: Article

References (27)

1. Loffet A.: J. Peptide Sci. 2002, 8, 1.
2. a) Olson G. L., Bolin D. R., Bonner M. P., Bös M., Cook C. M., Fry D. C., Graves B. J., Hatada M., Hill D. E., Khan M., Madison V. S., Rusiecki V. K., Sarabu R., Sepinwall J., Vincent G. P., Voss M. E.: J. Med. Chem. 1993, 36, 3039;
3. b) Gante J.: Angew. Chem., Int. Ed. Engl. 1994, 33, 1699;
4. c) Leung D., Abbenante G., Fairlie D. P.: J. Med. Chem. 2000, 43, 305.
5. a) Fletcher M. D., Campbell M. M.: Chem. Rev. (Washington, D. C.) 1998, 98, 763;
6. b) Goodman M., Chorev M.: Acc. Chem. Res. 1979, 12, 1;
7. c) Chorev M., Willson C. G., Goodman M.: J. Am. Chem. Soc. 1977, 99, 8075;
8. d) Chorev M., Goodman M.: Acc. Chem. Res. 1993, 26, 266;
9. e) Chorev M., Goodman M.: Trends Biotechnol. 1995, 13, 438.
10. a) Volonterio A., Bravo P., Zanda M.: Org. Lett. 2000, 2, 1827;
11. b) Volonterio A., Bravo P., Zanda M.: Tetrahedron Lett. 2001, 42, 3141;
12. c) Volonterio A., Bellosta S., Bravo P., Canavesi M., Corradi E., Meille V. S., Monetti M., Moussier N., Zanda M.: Eur. J. Org. Chem. 2002, 428.
13. See for example: Scolnick L. R., Clements A. M., Liao J., Crensha L., Hellberg M., May J., Dean T. R., Christianson D. W.: J. Am. Chem. Soc. 1997, 119, 850.
14. Volonterio A., Bravo P., Moussier N., Zanda M.: Tetrahedron Lett. 2000, 41, 6517.
15. For a monograph on solid-phase combinatorial synthesis: Obrecht D., Villalgordo J. M. in: Tetrahedron Organic Chemistry Series: Solid-Supported Combinatorial and Parallel Synthesis of Small-Molecular-Weight Compounds Libraries (J. E. Baldwin and R. M. Williams, Eds). Pergamon, Oxford 1998.
16. a) Shibuya A., Kurishita M., Ago C., Taguchi T.: Tetrahedron 1996, 52, 271;
17. b) Yamazaki T., Shinohara N., Kitazume T., Sato S.: J. Fluorine Chem. 1999, 97, 91.
18. Excess of 3 can be recovered quantitatively in a pure form just evaporating the organic solvent from the solution without any further purification.
19. 3)NH] center.
20. To our knowledge, these are the first examples reported in literature of solid-phase intermolecular Michael-type N-additions involving α-amino acid esters and 4-substituted acceptors. For some rare solution-phase examples, see: a) Leonard N. J., Fischer F. E., Barthel E., Jr., Figueras J., Jr., Wildman W. C.: J. Am. Chem. Soc. 1951, 73, 2371; b) Urbach H., Henning R.: Tetrahedron Lett. 1984, 25, 1143. For solid-phase conjugate 1,4-N-additions to unsubstituted acceptors, see: c) Morphy J. R., Rankovic Z., Rees D. C.: Tetrahedron Lett. 1996, 37, 3209; d) Kolodziej S. A., Hamper B. C.: Tetrahedron Lett. 1996, 37, 5277; e) Garibay P., Nielsen J., Hoeg-Jensen T.: Tetrahedron Lett. 1998, 39, 2207.
21. To our knowledge, these are the first examples reported in literature of solid-phase intermolecular Michael-type N-additions involving α-amino acid esters and 4-substituted acceptors. For some rare solution-phase examples, see: a) Leonard N. J., Fischer F. E., Barthel E., Jr., Figueras J., Jr., Wildman W. C.: J. Am. Chem. Soc. 1951, 73, 2371; b) Urbach H., Henning R.: Tetrahedron Lett. 1984, 25, 1143. For solid-phase conjugate 1,4-N-additions to unsubstituted acceptors, see: c) Morphy J. R., Rankovic Z., Rees D. C.: Tetrahedron Lett. 1996, 37, 3209; d) Kolodziej S. A., Hamper B. C.: Tetrahedron Lett. 1996, 37, 5277; e) Garibay P., Nielsen J., Hoeg-Jensen T.: Tetrahedron Lett. 1998, 39, 2207.
22. To our knowledge, these are the first examples reported in literature of solid-phase intermolecular Michael-type N-additions involving α-amino acid esters and 4-substituted acceptors. For some rare solution-phase examples, see: a) Leonard N. J., Fischer F. E., Barthel E., Jr., Figueras J., Jr., Wildman W. C.: J. Am. Chem. Soc. 1951, 73, 2371; b) Urbach H., Henning R.: Tetrahedron Lett. 1984, 25, 1143. For solid-phase conjugate 1,4-N-additions to unsubstituted acceptors, see: c) Morphy J. R., Rankovic Z., Rees D. C.: Tetrahedron Lett. 1996, 37, 3209; d) Kolodziej S. A., Hamper B. C.: Tetrahedron Lett. 1996, 37, 5277; e) Garibay P., Nielsen J., Hoeg-Jensen T.: Tetrahedron Lett. 1998, 39, 2207.
23. To our knowledge, these are the first examples reported in literature of solid-phase intermolecular Michael-type N-additions involving α-amino acid esters and 4-substituted acceptors. For some rare solution-phase examples, see: a) Leonard N. J., Fischer F. E., Barthel E., Jr., Figueras J., Jr., Wildman W. C.: J. Am. Chem. Soc. 1951, 73, 2371; b) Urbach H., Henning R.: Tetrahedron Lett. 1984, 25, 1143. For solid-phase conjugate 1,4-N-additions to unsubstituted acceptors, see: c) Morphy J. R., Rankovic Z., Rees D. C.: Tetrahedron Lett. 1996, 37, 3209; d) Kolodziej S. A., Hamper B. C.: Tetrahedron Lett. 1996, 37, 5277; e) Garibay P., Nielsen J., Hoeg-Jensen T.: Tetrahedron Lett. 1998, 39, 2207.
24. To our knowledge, these are the first examples reported in literature of solid-phase intermolecular Michael-type N-additions involving α-amino acid esters and 4-substituted acceptors. For some rare solution-phase examples, see: a) Leonard N. J., Fischer F. E., Barthel E., Jr., Figueras J., Jr., Wildman W. C.: J. Am. Chem. Soc. 1951, 73, 2371; b) Urbach H., Henning R.: Tetrahedron Lett. 1984, 25, 1143. For solid-phase conjugate 1,4-N-additions to unsubstituted acceptors, see: c) Morphy J. R., Rankovic Z., Rees D. C.: Tetrahedron Lett. 1996, 37, 3209; d) Kolodziej S. A., Hamper B. C.: Tetrahedron Lett. 1996, 37, 5277; e) Garibay P., Nielsen J., Hoeg-Jensen T.: Tetrahedron Lett. 1998, 39, 2207.
25. 19F NMR analysis.
26. Evans D. A., Britton T. C., Ellman J. A., Dorow R. L.: J. Am. Chem. Soc. 1990, 112, 4011.
27. This effect was also observed performing the reaction in solution. Volonterio A., Zanda M. et al.: Unpublished results.