Solid-Phase Synthesis of Multiple Classes of Peptidomimetics from Versatile Resin-Bound Aldehyde Intermediates

Author:

Scott William L.1,Martynow Jacek G.1,Huffman John C.1,O'Donnell Martin J.1

Affiliation:

1. Contribution from the Department of Chemistry and Chemical Biology, Indiana University Purdue University Indianapolis, Indianapolis, Indiana 46202-3274, and Department of Chemistry, Indiana University, Bloomington, Indiana 47405-4001

Publisher

American Chemical Society (ACS)

Subject

Colloid and Surface Chemistry,Biochemistry,General Chemistry,Catalysis

Reference38 articles.

1. Selected monographs and reviews related to peptidomimetics:  (a) Hirschmann, R.Angew.Chem.,Int. Ed. Engl.1991,30, 1278−1301. (b) Giannis, A.; Kolter, T.Angew.Chem.,Int. Ed. Engl.1993,32, 1244−1267. (c) 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.; Kahn, M.; Madison, V. S.; Rusiecki, V. K.; Sarabu, R.; Sepinwall, J.; Vincent, G. P.; Voss, M. E.J. Med. Chem.1993,36, 3039−3049. (d) Liskamp, R. M. J.Recl. Trav. Chim. Pays-Bas1994,113, 1−19. (e) Gante, J.Angew.Chem.,Int. Ed. Engl.1994,33, 1699−1720. (f) Gillespie, P.; Cicariello, J.; Olson, G. L.Biopolymers (Peptide Science)1997,43, 191−217. (g) Aubé, J.Adv. Amino Acid Mimetics Peptidomimetics1997,1, 193−232. (h) Hanessian, S.; McNaughton-Smith, G.; Lombart, H.G.; Lubell, W. D.Tetrahedron1997,53, 12789−12854. (i) Halab, L.; Gosselin, F.; Lubell, W. D.Biopolymers (Peptide Science)2000,55, 101−122. (j) Hruby, V. J.; Balse, P. M.Curr. Med. Chem.2000,7, 945−970. (k) Luthman, K.; Hacksell, U.Textbook of Drug Design and Discovery, 3rd ed.; 2002, pp 459−485. (l) Bursavich, M. G.; Rich, D. H.J. Med. Chem.2002,45, 541−558. (m) Synthesis of Peptides and Peptidomimetics. InHouben-Weyl,Methods in Organic Chemistry; Goodman, M., Felix, A., Moroder, L., Toniolo, C., Eds.; Thieme:  Stuttgart, New York, 2003; Vol. E22c. (n) Nakanishi, H.; Kahn, M. InPractice of Medicinal Chemistry, 2nd ed.; Wermuth, C. G., Ed.; Academic Press:  New York, 2003; Chapter 29, pp 477−500. (o) Freidinger, R. M.J. Med. Chem.2003,46, 5553−5566. (p) Schiller, P. W.; Weltrowska, G.; Schmidt, R.; Nguyen, T. M.D.; Berezowska, I.; Lemieux, C.; Chung, N. N.; Carpenter, K. A.; Wilkes, B. C.DrugDiscovery Strategies Methods2004, 147−173. (q) Martin-Martínez, M.; Patiño-Molina, R.; Garcia-López, M. T.; González-Muñiz, R.Mini-Rev. Med.Chem.2004,4, 669−680. (r) Andronati, S. A.; Karaseva, T. L.; Krysko, A. A.Curr. Med. Chem.2004,11, 1183−1211. (s) Belvisi, L.; Colombo, L.; Manzoni, L.; Potenza, D.; Scolastico, C.Synlett2004, 1449−1471. (t) Cowell, S. M.; Lee, Y. S.; Cain, J. P.; Hruby, V. J.Curr. Med. Chem.2004,11, 2785−2798. (u) Perdih, A.; Kikelj, D.Curr. Med. Chem.2006,13, 1525−1556. (v) Gentilucci, L.; Tolomelli, A.; Squassabia, F.Curr. Med.Chem.2006,13, 2449−2466.

2. Enantioselective synthesis of the depsipeptide unsaturated acid portion of madumycin II

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