Synthesis and structural characterisation as 12-helix of the hexamer of a beta-amino acid tethered to a pyrrolidin-2-one ring.

Starting from (3S,4R,1'S)-3-amino-2-oxo-1-[1'-(4-methoxyphenylethyl)]pyrrolidine carboxylic acid (2), the first synthesis of a beta-foldamer containing pyrrolidin-2-one rings is described, whose 12-helix conformation is assigned by NMR analysis and confirmed by molecular dynamics (MD) simulations.

[1]  Andrew H. Gordon,et al.  Glycosylated foldamers to probe the carbohydrate-carbohydrate interaction. , 2006, Journal of the American Chemical Society.

[2]  F. Fülöp,et al.  Application of alicyclic β-amino acids in peptide chemistry , 2006 .

[3]  A. Hamilton,et al.  Strategies for targeting protein-protein interactions with synthetic agents. , 2005, Angewandte Chemie.

[4]  G. Tew,et al.  Simple oligomers as antimicrobial peptide mimics , 2005, Journal of Industrial Microbiology and Biotechnology.

[5]  S. Rinaldi,et al.  Conformationally restricted analogues of both (S)-β-homoserine and (S)-aspartic acid from chiral 3-acylamino pyrrolidin-2-ones , 2005 .

[6]  R. P. Cheng,et al.  Beyond de novo protein design--de novo design of non-natural folded oligomers. , 2004, Current opinion in structural biology.

[7]  J. Bechhoefer,et al.  Self-assembly of the ionic peptide EAK16: the effect of charge distributions on self-assembly. , 2004, Biophysical journal.

[8]  Paul E. Smith,et al.  A Combined Simulation and Kirkwood−Buff Approach to Quantify Cosolvent Effects on the Conformational Preferences of Peptides in Solution , 2004 .

[9]  Bing Gong,et al.  Well-defined secondary structures. , 2004, European journal of biochemistry.

[10]  B. Roux,et al.  Energetics of ion conduction through the gramicidin channel , 2003, Proceedings of the National Academy of Sciences of the United States of America.

[11]  D. Seebach,et al.  Antibiotic and Hemolytic Activity of a β2/β3 Peptide Capable of Folding into a 12/10‐Helical Secondary Structure , 2003 .

[12]  Jin-seong Park,et al.  Accommodation of α-Substituted Residues in the β-Peptide 12-Helix: Expanding the Range of Substitution Patterns Available to a Foldamer Scaffold , 2003 .

[13]  Wonmuk Hwang,et al.  Design of nanostructured biological materials through self-assembly of peptides and proteins. , 2002, Current opinion in chemical biology.

[14]  V. Hruby.  Designing peptide receptor agonists and antagonists , 2002, Nature Reviews Drug Discovery.

[15]  S. Gellman,et al.  Structure-activity studies of 14-helical antimicrobial beta-peptides: probing the relationship between conformational stability and antimicrobial potency. , 2002, Journal of the American Chemical Society.

[16]  S. Gellman,et al.  Stereoselective synthesis of 3-substituted 2-aminocyclopentanecarboxylic acid derivatives and their incorporation into short 12-helical beta-peptides that fold in water. , 2002, Journal of the American Chemical Society.

[17]  S. Gellman,et al.  Synthesis and 12-helical secondary structure of beta-peptides containing (2R,3R)-aminoproline. , 2002, Organic letters.

[18]  S. Gellman,et al.  Mimicry of Host-Defense Peptides by Unnatural Oligomers: Antimicrobial β-Peptides , 2002 .

[19]  Matthew J. Mio,et al.  A field guide to foldamers. , 2001, Chemical reviews.

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

[21]  S. Gellman,et al.  Diversity in short beta-peptide 12-helices: high-resolution structural analysis in aqueous solution of a hexamer containing sulfonylated pyrrolidine residues. , 2001, Journal of the American Chemical Society.

[22]  S. Gellman,et al.  An efficient route to either enantiomer of orthogonally protected trans-3-aminopyrrolidine-4-carboxylic acid. , 2001, The Journal of organic chemistry.

[23]  J. Nowick,et al.  Designed molecules that fold to mimic protein secondary structures. , 1999, Current opinion in chemical biology.

[24]  A. Barron,et al.  Bioinspired polymeric materials: in-between proteins and plastics. , 1999, Current opinion in chemical biology.

[25]  Samuel H. Gellman,et al.  Foldamers: A Manifesto , 1998 .

[26]  G. R. Smith,et al.  Modelling and simulation of ion channels: applications to the nicotinic acetylcholine receptor. , 1998, Journal of structural biology.

[27]  J. Dauphin,et al.  Artifact-Free Pure Absorption PFG-Enhanced DQF-COSY Spectra Including a Gradient Pulse in the Evolution Period , 1997 .

[28]  D. Seebach,et al.  β-Peptides: a surprise at every turn , 1997 .

[29]  C. Dobson,et al.  The concept of a random coil: Residual structure in peptides and denatured proteins , 1996 .

[30]  J M Thornton,et al.  Analysis of main chain torsion angles in proteins: prediction of NMR coupling constants for native and random coil conformations. , 1996, Journal of molecular biology.

[31]  R. R. Ernst,et al.  Separation of cross-relaxation and J cross-peaks in 2D rotating-frame NMR spectroscopy , 1987 .

[32]  A. Bax,et al.  1H and13C Assignments from Sensitivity-Enhanced Detection of Heteronuclear Multiple-Bond Connectivity by 2D Multiple Quantum NMR , 1986 .

[33]  R. Griffey,et al.  Correlation of proton and nitrogen-15 chemical shifts by multiple quantum NMR☆ , 1983 .