A multi-component reaction (MCR) approach to the synthesis of highly diverse polymers with polypeptide-like features

Molecular Diversity

Volumn 6, Issue 3-4, 2003, Pages 237-244

  Robotham, Claude V ^a   Baker, Christopher ^a   Cuevas, Brian ^b   Abboud, Khalil ^a   Wright, Dennis L ^a  

^a University of Florida ^*  (United States)

^b University of Florida   (United States)

Author keywords

Metathesis; Multi component coupling; Polymer synthesis; ROMP; Ugi reaction

Indexed keywords

ACID; ALDEHYDE; AMINE; CARBOXYLIC ACID DERIVATIVE; ISONITRILE DERIVATIVE; NORBORNENE DERIVATIVE; POLYMER; POLYPEPTIDE; RUTHENIUM;

CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHIRALITY; CONFERENCE PAPER; MULTICOMPONENT REACTION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; RING OPENING METATHESIS POLYMERIZATION; STEREOCHEMISTRY; SYNTHESIS; UGI REACTION;

CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; MOLECULAR STRUCTURE; PEPTIDES; POLYMERS;

EID: 0347132225     PISSN: 13811991     EISSN: None     Source Type: Journal    
DOI: 10.1023/B:MODI.0000006777.63423.40     Document Type: Conference Paper

References (30)

1. For examples see: (a) Rishton, G. M., Retz, D. M, Tempest, P. M., Novotny, J., Kahn, J., Treanor, J. S., Lile, J. D. and Citron, M., Fenchylamine sulfonamide inhibitors of β-amyloi peptide production by the γ-secretase proteolytic pathway: Potential small-molecule therapeutic agents for the treatment of alz heimer's disease, J. Med. Chem., 43 (2000) 2297-2299.
2. (b) Karan, C. and Miller, B. L. Dynamic diversity in drug discovery: Putting small-molecule evolution to work, Drug Design Trends, 5 (2000) 67-75.
3. (c) Frutos, O. and Curran, D., Solution phase synthesis of libraries of polycyclic natural product analogues by cascade radical annulation: synthesis of a 64-member library of mappicine analogues anda 48-member library of mappicine ketone analogues, J. Comb. Chem., 2 (2000) 639-649.
4. For examples see: (a) Uozumi, Y., Mizutani, K. and Nagai, S., A parallel preparation of a bicyclic N-chiral amine library and its use for chiral catalyst screening, Tetrahedron Letter, 42 (2001) 407-410.
5. (b) Miller, S. J. and Copeland, G. T. A chemosensor-based approach to catalyst discovery in solution and on solid support, J. Am. Chem. Soc., 121 (1999) 4306-4307.
6. For an example see: Gilbertson, S. R., Chen, G., Kao, J., Beatty, A. and Campana, C. F., Structure of phosphorous-containing peptide ligands. X-ray and NMR structural study of free ligand and Rhodium complex, J. Org. Chem., 62 (1997) 5557-5566.
7. Xiang, X-D. and Schultz, P. G., Combinatorial approaches to materials science. Current Opinion in Solid State & Materials Science, 3 (1998) 153-158.
8. Basso, A., Banfi, L., Riva, R., Piaggio, P. and Guanti, G., Solid-phase synthesis of modified oligopeptides via Passerini multicomponent reaction, Tetrahedron Letters, 44 (2003) 2367-2370.
9. de Nooy, A. E. J., Masci, G. and Crescenzi, V., Versatile synthesis of polysaccharide hydrogels using the Passerini and Ugi multicomponent condensations, Macromolecules, 32 (1999) 1318-1320.
10. Presented in part at The Second International Conference on Multicomponent Reactions, Combinatorial and Related Chemistry, Genoa, Italy, April 14-16, 2003.
11. Heck, S. and Ugi, I., The multicomponent reactions in the combinatorial synthesis af natural and preparative chemistry, Combinatorial Chemistry & High Throughput Screening, 4 (2001) 1-34.
12. Ugi, I., Domling, A. and Horl, W., Multicomponent reactions in organic chemistry, Endeavour, 3 (1994) 115.
13. Trost, B. M. and Hachiya, I., Assymetric molybdenum-catalyzed alkylations, J. Am. Chem. Soc., 120 (1998) 1104-1105.
14. (a) Murara, H., Sanda, F. and Endo, T. Highly radical-polymerizable methacrylamide having dipeptide structure. Macromolecules, 29, (1996) 5535-5538.
15. (b) Langer, R. Biomaterials in Drug Delivery and Tissue Engineering: One Laboratory's Experience, Acc. Chem. Res., 33 (2000) 94-109.
16. For reviews on catalytic olefin metathesis, see: (a) Grubbs, R. H., Miller, S. J., Fu, G. C. Acc. Chem. Res., 28, (1995) 446-452.
17. (b) Schmalz, H,-G., Angew. Chem., Int. Ed., 34, (1995) 1833-1836.
18. (c) Schuster, M. and Blechert, S., Angew. Chem., Int. Ed., 36, (1997) 2036-2056.
19. (d) Wright, D.L., Curr. Org. Chem., 3, (1999) 211-240.
20. (a) Liaw, D,-J, Tsai, J,-S and Wu, P,-L., polynorbornene with cross-linkable side chains via ring-opening metathesis polymerization, Macromolecules, 33 (2000) 6925-6929.
21. (b) Nomura, K. and Schrock, R. R., Preparation of 'Sugar-Coated' homopolymers and multiblock ROMP copolymers, Macromolecules, 29 (1996) 540-545.
22. (c) Maynard, H. D., Okada, S. and Grubbs, R. H., Synthesis of Norbornenyl polymers with bioactive Oligopeptides by ring-opnening metathesis polymerization, Macromolecules, 33 (2000) 6239-6248.
23. (d) Roberts, K. S. and Sampson, N. S., Increased Polymer Length of Oligopeptide-Substituted Polynorbornenes with LiCl, J. Org. Chem., 68 (2003), 2020-2023.
24. I. Ugi, U. Fetzer, U. Eholzer, H. and Knupfer, K., Neuere Methoden der präparativen organischen Chemie IV. Isonitril-Synthesen, Angew. Chem., 77 (1965) 492-504;
25. Angew. Chem. Int. Ed. Engl., 4 (1965) 452-464.
26. 2 R = CHR olefin metathesis catalysts: An organometallic success story, Acc. Chem. Res., 34 (2000) 18-29.
27. Bielawski, C. W. and Grubbs, R. H., Highly efficient ring-opening metathesis polymerization (ROMP) using new Ruthenium catalysts containing N-heterocyclic carbene ligands, Angew. Chem. Int., Ed., 39 (2000) 2903-2906.
28. Corey, E. J., Shibata, T. and Lee, T. W., Asymmetric Diels-Alder reactions catalyzed by a triflic acid activated chiral oxazaborolidine, J. Am. Chem. Soc., 124 (2002) 3808-3809.
29. 2.
30. Sheldrick, G. M. (1998). SHELXTL5. Bruker-AXS, Madison, Wisconsin, USA.