Soluble polymer supported synthesis of α-amino acid derivatives

Journal of Combinatorial Chemistry

Volumn 2, Issue 2, 2000, Pages 134-142

  Sauvagnat, Bérengère ^a   Kulig, Katarzyna ^b   Lamaty, Frédéric ^a   Lazaro, René ^a   Martinez, Jean ^a  

^a UNIVERSITÉ DE MONTPELLIER   (France)

^b JAGIELLONIAN UNIVERSITY MEDICAL COLLEGE   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; CARBONIC ACID DERIVATIVE; GLYCINE; MACROGOL DERIVATIVE; POLYMER; POTASSIUM; POTASSIUM CARBONATE; SCHIFF BASE;

ALKYLATION; ARTICLE; CATALYSIS; CHEMISTRY; SYNTHESIS;

ALKYLATION; AMINO ACIDS; CARBONATES; CATALYSIS; GLYCINE; POLYETHYLENE GLYCOLS; POLYMERS; POTASSIUM; SCHIFF BASES;

EID: 0034152325     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc9900605     Document Type: Article

References (38)

1. (a) Solid-supported Combinatorial and Parallel Synthesis of Small-Molecular-Weight Compound Libraries; Obrecht, D., Villalgordo, J. M., Eds.; Tetrahedron Organic Chemistry Series, Volume 17; Pergamon: New York, 1998.
2. (b) Combinatorial Chemistry: Synthesis and Application; Wilson, S. R., Czarnik, A. W., Eds.; John Wiley & Sons: New York, 1997.
3. Terrett, N. K. Combinatorial Chemistry; Compton, R. G., Davies, S. G., Evans, J., Eds.; Oxford University Press: Oxford, 1998.
4. A Practical Guide to Combinatorial Chemistry; Czarnik, A. W., DeWitt, S. H., Eds.; American Chemical Society: Washington, DC, 1997.
5. Bayer, E. Towards the Chemical Synthesis of Proteins. Angew. Chem., Int. Ed. Engl. 1991, 30, 113-129.
6. (a) Gravert, D. J.; Janda, K. D. Organic Synthesis on Soluble Polymer Supports: Liquid-Phase Methodologies Chem. Rev. 1997, 97, 489-509.
7. (b) Han, H.; Wolfe, M. M.; Brenner, S.; Janda, K. D. Liquid-Phase Combinatorial Synthesis. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 6419-6423.
8. (a) Sauvagnat, B.; Enjalbal, C.; Lamaty, F.; Lazaro, R.; Martinez, J.; Aubagnac; J.-L. Step-by-step monitoring of a liquid-phase organic synthesis by electrospray mass spectrometry. Rapid Commun. Mass Spectrom. 1998, 12, 1034-1037.
9. (b) Nativel, F.; Enjalbal, C.; Lamaty, F.; Lazaro, R.; Martinez, J.; Aubagnac, J.-L. Electrospray mass spectrometry analysis of liquid-phase organic synthesis. Eur. Mass Spectrom. 1998, 4, 233-237.
10. Enjalbal, C.; Sauvagnat, B.; Lamaty, F.; Lazaro, R.; Martinez, J.; Mouchet, P.; Roux, F.; Aubagnac, J.-L. Chemical Reactivity in Matrix-assisted Laser Desorption/Ionization Mass Spectrometry Rapid Commun. Mass Spectrom. 1999, 13, 1775-1781.
11. (a) For a preliminary report, see: Sauvagnat, B.; Lamaty, F.; Lazaro, R.; Martinez, J. Polyethylene Glycol (PEG) as Polymeric Support and Phase-transfer Catalyst in the Soluble Polymer Liquid-Phase Synthesis of α-Amino Esters. Tetrahedron Lett. 1998, 39, 821-824.
12. (b) Sauvagnat, B.; Lamaty, F.; Lazaro, R.; Martinez, J. Poly(ethylene glycol) (PEG) as a new phase-transfer catalyst in the palladium-catalyzed Heck reaction: positive effect of the polymer in the supported synthesis of α-aminoesters. C. R. Acad. Sci. Paris, Série IIc 1998, 1, 777-780.
13. O'Donnell, M. J.; Esikova, I. A.; Mi, A.; Shullenberger, D. F.; Wu, S. Amino Acid and Peptide Synthesis Using Phase-Transfer Catalysis. In Phase Transfer Catalysis, Mechanisms and Syntheses; Halpern, M. E., Ed.; ACS Symposium Series 659; American Chemical Society: Washington, DC, 1996; p 124-135.
14. O'Donnell, M. J.; Wojciechowski, K.; Ghosez, L.; Navarro, M.; Sainte, F.; Antoine, J.-P. Alkylation of Protected α-Amino Acid Derivatives in the Presence of Potassium Carbonate. Synthesis 1984, 313-315.
15. Zalipsky, S.; Gilon, C.; Zilkha, A. Esterification of Polyethylene Glycols. J. Macromol Sci.-Chem. 1984, A21, 839-845.
16. O'Donnell, M. J.; Polt, R. L. A Mild and Efficient Route to Schiff Base Derivatives of Amino Acids. J. Org. Chem. 1982, 47, 2663-2665.
17. Sieber, F.; Wentworth, P., Jr.; Toker, J. D.; Wentworth, A. D.; Metz, W. A.; Reed, N. N.; Janda, K. D. Development and Application of a Poly(ethylene glycol)-Supported Triarylphosphine Reagent: Expanding the Sphere of Liquid-Phase Organic Synthesis. J. Org. Chem. 1999, 64, 5188-5192.
18. van der Werf, A.; Kellogg, R. M. Synthesis of Some Proline Derivatives by Means of Michael Additions of Glycine Esters. Tetrahedron Lett. 1991, 32, 3727-3730.
19. Pillai, V. N. R.; Mutter, M. Conformational studies of poly(oxyethylene)-bound peptides and protein sequences. Acc. Chem. Res. 1981, 14, 122-130.
20. 3. See Experimental Section for more details. For a reference: Blettner, C. G.; König, W. A.; Stenzel, W.; Schotten, T. Poly(ethylene glycol) supported liquid-phase synthesis of biaryls. Synlett 1998, 295-297.
21. 3. See Experimental Section for more details. For a reference: Blettner, C. G.; König, W. A.; Stenzel, W.; Schotten, T. Poly(ethylene glycol) supported liquid-phase synthesis of biaryls. Synlett 1998, 295-297.
22. (a) Totten, G. E.; Clinton, N. A. Poly(ethylene Glycol) and Derivatives as Phase Transfer Catalysts and Solvents for Organic Reactions. J. M. S. -Rev. Macromol. Chem. Phys. 1988, C28, 293-337.
23. (b) Totten, G. E.; Clinton, N. A.; Matlock, P. L. Poly(ethylene Glycol) and Derivatives as Phase Transfer Catalysts. J. M. S. -Rev. Macromol. Chem. Phys. 1998, C38, 77-142.
24. (a) Yan, B. Monitoring the Progress and the Yield of Solid-phase Organic Reactions Directly on Resin Supports. Acc. Chem. Res. 1998, 31, 621-630 and references therein.
25. (b) Czarnik, A. W. Solid-Phase Synthesis Supports Are Like Solvents. Biotechnol. Bioeng. (Comb. Chem.) 1998, 61, 77-79.
26. Li, W.; Xiao, X.; Czarnik, A. W. Kinetic Comparison of Amide Formation on Various Cross-Linked Polystyrene Resins. J. Comb. Chem. 1999, 1, 127-129.
27. (a) Bayer, E.; Mutter, M.; Uhmann, R.; Polster, J.; Mauser, H. Kinetic Studies in the Liquid-Phase Peptide Synthesis. J. Am. Chem. Soc. 1974, 96, 7333-7336.
28. (b) Bergbreiter, D. E.; Kimmel, T.; Caraway, J. W. Modification of Substrate Reactivity Using Soluble Polymeric Supports. Tetrahedron Lett. 1995, 36, 4757-4760.
29. Metha, S.; Whitfield, D. Beneficial Participation of the Polymer: Improvement in Polymer-Supported Oligosaccharide Synthesis. Tetrahedron Lett. 1998, 39, 5907-5910.
30. Blettner, C. G.; König, W. A.; Stenzel, W.; Schotten, T. Highly Stereoselective Preparation of 3,3-Disubstituted Acrylates on Polyethylene Glycol. Tetrahedron Lett. 1999, 40, 2101-2102.
31. Gokel, G. W.; Goli, D. M.; Schultz, R. A. Binding Profiles for Oligoethylene Glycols and Oligoethylene Glycol Monomethyl Ethers and an Assessment of Their Abilities To Catalyze Phase-Transfer Reactions. J. Org. Chem. 1983, 48, 2837-2842.
32. (a) O'Donnell, M. J.; Zhou, C.; Scott, W. L. Solid-Phase Unnatural Peptide Synthesis (UPS). J. Am. Chem. Soc. 1996, 118, 6070-6071.
33. (b) O'Donnell, M. J.; Lugar, C. W.; Pottorf, R. S.; Zhou, C.; Scott, W. L.; Cwi, C. L. Solid-Phase Synthesis of Unnatural Amino Acids using Unactivated Alkyl Halides. Tetrahedron Lett. 1997, 38, 7163-7166.
34. O'Donnell, M. J.; Delgado, F.; Pottorf, R. S. Enantioselective Solid-Phase Synthesis of α-Amino Acid derivatives. Tetrahedron 1999, 55, 6347-6362.
35. The hydrogen abstraction from 3 can be also performed with LDA at -78 °C in THF. Sauvagnat, B.; Lamaty, F.; Lazaro, R.; Martinez, J. Unpublished results.
36. Polt, R.; Peterson, M. A.; DeYoung, L. Aluminoxy Acetals from α-Amino esters: Chirality Transfer via Sequential Addition of Hydride and C-Nucleophiles. 2-Amino Alcohols and Sphingosines. J. Org. Chem. 1992, 57, 5469-5480.
37. Genet, J.-P.; Juge, S.; Achi, S.; Mallart, S. Ruiz Montes, J.; Leviq, G. Synthesis of α-amino acids using transition metal catalysis -Alkylation of Schiff bases derived from α-amino acid esters (regio, stereoselectivity). Tetrahedron 1988, 44, 5263-5275.
38. Crisp, G. T.; Gebauer, M. G. The hydrostannation of propargylglycine derivative. J. Organomet. Chem. 1997, 532, 83-88.