Synthesis of conformationally tailored pentaazacyclopentadeeanes. Preorganizing peptide cyclizations.

Tetrahedron Letters

Volumn 38, Issue 5, 1997, Pages 779-782

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

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPEPTIDE; MACROCYCLIC COMPOUND;

ARTICLE; CHIRALITY; CYCLIZATION; DRUG SYNTHESIS; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PEPTIDE SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031025475     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02446-X     Document Type: Article

References (16)

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3. (c) Weiss, R.H.; Flickinger, A.G.; Rivers, W.J.; Hardy, M.M.; Aston, K.W.; Ryan, U.S.; Riley, D.P. J. Biol. Chem. 1993,268, 23049.
4. Aston, K.W.; Henke, S.L.; Modak, A.S.; Riley, D.P.; Sample, K.R.; Weiss, R.H.; Neumann, W.L. Tetrahedron Lett. 1994, 35, 3687.
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9. (e) Bogusky, M.J.; Brady, S.F.; Sisko, J.T.; Nutt, R.F.; Smity, GM. Int. J. Pept. Protein Res. 1993, 42, 194.
10. Rose, G.D.; Gierasch, L.M.; Smith, J.A. Adv. Protein Chemistry 1985, 37,1.
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14. (a) For example of a cis-amide bond surrogate see: Abell, A.D.; Hoult, D.A.; Jamieson, E.J. Tetrahedron Lett. 1992, 33, 5831.
15. (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.
16. Stroup, A.N.; Rockwefl, A.L.; Rhiengold, A.L.; Gierasch, L.M. J. Am. Chem. Soc. 1988, 110, 5157 and references cited therein.