Stereoselective synthesis of 6,5-bicyclic reverse-turn peptidomimetics

Tetrahedron

Volumn 54, Issue 20, 1998, Pages 5325-5336

  Colombo, Lino ^a   Di Giacomo, Marcello ^a   Brusotti, Gloria ^a   Sardone, Nicola ^a   Angiolini, Mauro ^b   Belvisi, Laura ^b   Maffioli, Sonia ^b   Manzoni, Leonardo ^b   Scolastico, Carlo ^b  

^a UNIVERSITY OF PAVIA   (Italy)

^b UNIVERSITY OF MILAN   (Italy)

Author keywords

Bicyclic aliphatic compounds; Conformation; Lactams; Peptide mimetics

Indexed keywords

LACTAM; PEPTIDE DERIVATIVE;

ARTICLE; CRYSTAL STRUCTURE; PEPTIDE SYNTHESIS; PRIORITY JOURNAL; PROTEIN CONFORMATION; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS; SYNTHESIS; X RAY ANALYSIS;

EID: 0032516293     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00207-5     Document Type: Article

References (24)

1. [1] Gallop MA, Barrett RW, Dower WJ, Fodor SPA, Gordon EM. J. Med. Chem. 1994;37:1233-1251.
2. [2] Gordon EM, Barrett RW, Dower WJ, Fodor SPA, Gallop MA. J. Med. Chem. 1994;37:1385-1401.
3. [3] Giannis A, Kolter T. Angew. Chem. Int. Ed. Eng. 1993;32:1244-1267.
4. [4] Gante J. Angew. Chem. Int. Ed. Eng. 1994;33:1699-1720.
5. [5] Kahn M, editor. Peptide Secondary Structure Mimetics. Tetrahedron Symposia-in-Print No. 50, 1993;49:3433-3689.
6. [6] Ball JB, Hughes RA, Alewood PF, Andrews PR. Tetrahedron 1993;49:3467-3478.
7. [7] Kitagawa O, Velde DV, Dutta D, Morton M, Takusagawa F, Aubé J. J. Am. Chem. Soc. 1995;117:5169-5178.
8. [8] Colombo L, Di Giacomo M, Belvisi L, Manzoni L, Scolastico C, Salimbeni A. Gazz. Chim. It. 1996;126:543-554.
9. [9] Colombo L, Di Giacomo M, Scolastico C, Manzoni L, Belvisi L, Molteni V. Tetrahedron Lett. 1995;36:625-628.
10. [10] Hanessian S, McNaughton-Smith G, Lombart HG, Lubell WD. Tetrahedron Report No. 426. Tetrahedron 1997;53:12789-12854 and references therein.
11. [11] Kim K, Dumas JP, Germanas JP. J. Org. Chem. 1996;61:3138-3144.
12. [12] Li W, Hanau CE, d'Avignon A, Moeller KD. J. Org. Chem. 1995;60:8155-8170.
13. [13] Mohamadi F, Richards NGJ, Guida WC, Liskamp R, Lipton M, Caufield C, Chang G, Hendrickson T, Still WC. J. Comput. Chem. 1990;11:440-467.
14. [14] Chang G, Guida WC, Still WC. J. Am. Chem. Soc. 1989;111:4379-4386.
15. [15] Weiner SJ, Kollman PA, Nguyen DT, Case DA. J. Comput. Chem. 1986;7:230-252.
16. [16] Still WC, Tempczyk A, Hawley RC, Hendrickson T. J. Am. Chem. Soc. 1990;112:6127-6129.
17. [17] Richardson JS. Adv. Protein Chem. 1981;34:167-339.
18. [18] Slomczynska U, Chalmers DK, Cornille F, Smythe ML, Beusen DD, Moeller KD Marshall GR. J. Org. Chem. 1996;61:1198-1204.
19. [19] Chalmers DK, Marshall GR. J. Am. Chem. Soc. 1995;117:5927-5937.
20. [20] Stewart JJP. MOPAC Version 6.0, F.J. Seiler Research Laboratory, U.S. Air Force Academy, CO 80840, QCPE 455.
21. [21] Chiesa MV, Manzoni L, Scolastico C. Synlett 1996;5:441-443.
22. [22] Högberg T, Ström P, Ebner M, Rämsby S. J. Org. Chem. 1987;52:2033-2036.
23. [23] Huang X, Keillor JW. Tetrahedron Lett. 1997;38:313-316 and references therein.
24. [24] Kajigaeshi S, Asano K, Fujisaki S, Kakinami T, Okamoto T. Chem. Lett. 1989;463-464.