Conformational stability studies of a stapled hexa-β3-peptide library.

A library of 14-helical hexa β(3)-peptides was synthesized in order to determine the influence of sequence variation as well as staple size and location on conformational stability. From this study we show that appropriately stapled hexa-β(3)-peptides can allow for a number of variations without significant perturbation of the 14-helix.

[1]  Arjel D. Bautista,et al.  Bridged beta(3)-peptide inhibitors of p53-hDM2 complexation: correlation between affinity and cell permeability. , 2010, Journal of the American Chemical Society.

[2]  M. Ebert,et al.  Synthesis and High-Resolution NMR Structure of a β3-Octapeptide with and without a Tether Introduced by Olefin Metathesis , 2009 .

[3]  Jordan M Fletcher,et al.  Synthesis of stapled beta3-peptides through ring-closing metathesis. , 2009, Organic letters.

[4]  S. Gellman,et al.  Comparison of Design Strategies for Promotion of β‐Peptide 14‐Helix Stability in Water , 2008, Chembiochem : a European journal of chemical biology.

[5]  L. Brunsveld,et al.  Stable Helicalβ3-Peptides in Water via Covalent Bridging of Side Chains , 2006 .

[6]  A. Schepartz,et al.  Relationship between salt-bridge identity and 14-helix stability of beta3-peptides in aqueous buffer. , 2006, Organic letters.

[7]  B. Jaun,et al.  Design, synthesis and structural investigations of a beta-peptide forming a 314-helix stabilized by electrostatic interactions. , 2004, Chemistry.

[8]  Alanna Schepartz,et al.  Helix macrodipole control of β3-peptide 14-helix stability in water , 2003 .

[9]  P. Perlmutter,et al.  β-amino acids: Versatile peptidomimetics , 2002 .

[10]  W. DeGrado,et al.  beta-Peptides: from structure to function. , 2001, Chemical reviews.

[11]  D. Seebach,et al.  On the Antimicrobial and Hemolytic Activities of Amphiphilic β‐Peptides , 2001 .

[12]  W. DeGrado,et al.  De novo design of a monomeric helical beta-peptide stabilized by electrostatic interactions. , 2001, Journal of the American Chemical Society.

[13]  H. Mizutani,et al.  Modular peptide-based phosphine ligands in asymmetric catalysis: efficient and enantioselective Cu-catalyzed conjugate additions to five-, six-, and seven-membered cyclic enones. , 2001, Journal of the American Chemical Society.

[14]  G. Verdine,et al.  An All-Hydrocarbon Cross-Linking System for Enhancing the Helicity and Metabolic Stability of Peptides , 2000 .

[15]  B. Jaun,et al.  NMR Structure in methanol of a β-hexapeptide with a disulfide clamp , 2000 .