Pseudopeptide synthesis of a pentaazamacrocycle containing two transfused cyclohexane rings

Tetrahedron Letters

Volumn 38, Issue 18, 1997, Pages 3143-3146

  Neumann, William L ^a   Franklin, Gary W ^a   Sample, Kirby R ^a   Aston, Karl W ^a   Weiss, Randy H ^a   Riley, Dennis P ^a   Rath, Nigam ^b  

^a MONSANTO COMPANY   (United States)

^b UNIVERSITY OF MISSOURI ST LOUIS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

MACROCYCLIC COMPOUND; PSEUDOPEPTIDE;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; X RAY CRYSTALLOGRAPHY;

EID: 0030998710     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00563-7     Document Type: Article

References (12)

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2. Lennon, P.J.; Rahman, H.; Aston, K.W.; Henke, S.L.; Riley, D.P. Tetrahedron Lett. 1994, 35, 853.
3. (a) Veber, D.; Brady, S.F.; Varga, S.L.; Freidinger, R.M.; Schwenk, D.A.; Mendlowski, M.; Holly, F.W. J. Org. Chem. 1979, 44, 3101.
4. (b) Bodanszky, M.; Bodanszky, A.; The Practice of Peptide Synthesis; Springer-Verlag: Berlin, 1984.
5. (c) Kopple, K.D. J. Pharm. Sci. 1972, 61, 1345.
6. (a) Rose, G.D.; Gierasch, L.M.; Smith, J.A. Adv. Protein Chemistry 1985, 37,1.
7. (b) For Numerous references concerning the incorporation of conformationally rigid molecules into peptides to stabilize a single conformation and for the design and synthesis of β-turn mimetics see: Tsang, K.Y.; Diaz, H.; Graciani, N.; Kelly, J.W. J. Am. Chem. Soc. 1994, 116, 3988.
8. 2. Studies designed to illucidate the mechanism of this reaction are ongoing and will be reported in the future.
9. Liang, G. B.; Desper, J. M.; Gellman, S. H. J. Am. Chem. Soc. 1993, 115, 925.
10. (a) Kessler, H. Angew. Chem. Int. Ed. Engl. 1982, 21, 512.
11. (b) Bode, K.; Goodman, M.; Mutter, M. Helv. Chim. Acta 1985, 68, 705.
12. (c) Gierasch, L. Ph.D. Thesis, Harvard University, April, 1985.