An efficient approach to asymmetric synthesis of dipeptide β-turn mimetics: indolizidinone amino acids

Author:

Wang Wei,Xiong Chiyi,Hruby Victor J

Publisher

Elsevier BV

Subject

Organic Chemistry,Drug Discovery,Biochemistry

Reference15 articles.

1. Recent reviews for design and synthesis of ‘dipeptide-turn mimetics’: (a) Halab, L.; Gosselin, F.; Lubell, W. D. Biopolym. (Pept. Sci.) 2000, 55, 101–122; (b) Hanessian, S.; McNaughton-Smith, G.; Lombart, H.-G.; Lubell, W. D. Tetrahedron 1997, 53, 12789–12854. Reviews for the applications of peptidomimetics including turn mimetics: (c) Giannis, A.; Kolter, T. Angew. Chem., Int. Ed. Engl. 1993, 23, 1244–1247; (d) Gante, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1699–1720.

2. Reviews regarding conformational and topographical considerations in designing peptidomimetics including turn mimetics: (a) Hruby, V. J. Life Sci. 1982, 31, 189–199; (b) Hruby, V. J.; Al-Obeidi, F.; Kazmierski, W. M. Biochem. J. 1990, 268, 249–262; (c) Hruby, V. J.; Balse, P. M. Curr. Top. Med. Chem. 2000, 7, 945–970.

3. Examples for incorporation of turn mimetics into peptides: (a) Dolle, R. E.; Prasad, C. V. C.; Prouty, C. P.; Salvino, J. M.; Awad, M. M. A.; Schmidt, S. J.; Hoyer, D.; Ross, T. M.; Graybill, T. L.; Speier, G. J.; Uhl, J.; Miller, B. E.; Helaszek, C. T.; Ator, M. A. J. Med. Chem. 1997, 40, 1941–1946; (b) Baures, P. W.; Ojala, W. H.; Costain, W. J.; Ott, M. C.; Pradhan, A.; Gleason, W. B.; Mishra, R. K.; Johnson, R. L. J. Med. Chem. 1997, 40, 3594–3600; (c) Haubner, R.; Schmitt, W.; Holzemann, G.; Goodman, S. L.; Jonczyk, A.; Kessler, H. J. Am. Chem. Soc. 1996, 118, 7881–7891; (d) Claridge, T. D. W.; Hulme, C.; Kelly, R. J.; Lee, V.; Nash, I. A.; Schofield, C. J. Bioorg. Med. Chem. Lett. 1996, 6, 485–490; (e) Liu, R.; Dong, D. L.-Y.; Sherlock, R.; Nestler, H. P. Bioorg. Med. Chem. Lett. 1999, 9, 847–852; (f) Karanewsky, D. S.; Bai, X.; Linton, S. D.; Krebs, J. F.; Wu, J.; Pham, B.; Tomaselli, K. J. Bioorg. Med. Chem. Lett. 1998, 8, 2757–2762.

4. [half-Cys4,half-Cys10]-alpha-Melanocyte-stimulating hormone: a cyclic alpha-melanotropin exhibiting superagonist biological activity.

5. Design of a new class of superpotent cyclic .alpha.-melanotropins based on quenched dynamic simulations

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