Literature DB >> 20491510

Helix formation in preorganized beta/gamma-peptide foldamers: hydrogen-bond analogy to the alpha-helix without alpha-amino acid residues.

Li Guo1, Aaron M Almeida, Weicheng Zhang, Andrew G Reidenbach, Soo Hyuk Choi, Ilia A Guzei, Samuel H Gellman.   

Abstract

We report the first high-resolution structural data for the beta/gamma-peptide 13-helix (i,i+3 C=O...H-N H-bonds), a secondary structure that is formed by oligomers with a 1:1 alternation of beta- and gamma-amino acid residues. Our characterization includes both crystallographic and 2D NMR data. Previous studies suggested that beta/gamma-peptides constructed from conformationally flexible residues adopt a different helical secondary structure in solution. Our design features preorganized beta- and gamma-residues, which strongly promote 13-helical folding by the 1:1 beta/gamma backbone.

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Year:  2010        PMID： 20491510      PMCID： PMC2904518          DOI： 10.1021/ja103233a

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  34 in total

1.  Artificial beta-barrels.

Authors:  Naomi Sakai; Jiri Mareda; Stefan Matile
Journal:  Acc Chem Res       Date:  2008-07-01       Impact factor: 22.384

2.  Structural and biological mimicry of protein surface recognition by alpha/beta-peptide foldamers.

Authors:  W Seth Horne; Lisa M Johnson; Thomas J Ketas; Per Johan Klasse; Min Lu; John P Moore; Samuel H Gellman
Journal:  Proc Natl Acad Sci U S A       Date:  2009-08-17       Impact factor: 11.205

3.  Stabilisation of Peptide foldamers in an aqueous medium by incorporation of azapeptide building blocks.

Authors:  Anasztázia Hetényi; Gábor K Tóth; Csaba Somlai; Elemér Vass; Tamás A Martinek; Ferenc Fülöp
Journal:  Chemistry       Date:  2009-10-19       Impact factor: 5.236

4.  Evaluation of triazolamers as active site inhibitors of HIV-1 protease.

Authors:  Andrea L Jochim; Stephen E Miller; Nicholas G Angelo; Paramjit S Arora
Journal:  Bioorg Med Chem Lett       Date:  2009-09-17       Impact factor: 2.823

5.  Theoretical and experimental studies on alpha/epsilon-hybrid peptides: design of a 14/12-helix from peptides with alternating (S)-C-linked carbo-epsilon-amino acid [(S)-epsilon-Caa((x))] and L-ala.

Authors:  Gangavaram V M Sharma; Bommagani Shoban Babu; Deepak Chatterjee; Kallaganti V S Ramakrishna; Ajit C Kunwar; Peter Schramm; Hans-Jörg Hofmann
Journal:  J Org Chem       Date:  2009-09-04       Impact factor: 4.354

6.  Identification of a beta3-peptide HIV fusion inhibitor with improved potency in live cells.

Authors:  Arjel D Bautista; Olen M Stephens; Ligong Wang; Robert A Domaoal; Karen S Anderson; Alanna Schepartz
Journal:  Bioorg Med Chem Lett       Date:  2009-05-15       Impact factor: 2.823

7.  Synthesis and structure of alpha/delta-hybrid peptides--access to novel helix patterns in foldamers.

Authors:  Gangavaram V M Sharma; Bommagani Shoban Babu; Kallaganti V S Ramakrishna; Pendem Nagendar; Ajit C Kunwar; Peter Schramm; Carsten Baldauf; Hans-Jörg Hofmann
Journal:  Chemistry       Date:  2009       Impact factor: 5.236

8.  De novo design and in vivo activity of conformationally restrained antimicrobial arylamide foldamers.

Authors:  Sungwook Choi; Andre Isaacs; Dylan Clements; Dahui Liu; Hyemin Kim; Richard W Scott; Jeffrey D Winkler; William F DeGrado
Journal:  Proc Natl Acad Sci U S A       Date:  2009-04-09       Impact factor: 11.205

9.  Foldamers with heterogeneous backbones.

Authors:  W Seth Horne; Samuel H Gellman
Journal:  Acc Chem Res       Date:  2008-07-01       Impact factor: 22.384

10.  Expanding the peptide beta-turn in alphagamma hybrid sequences: 12 atom hydrogen bonded helical and hairpin turns.

Authors:  Sunanda Chatterjee; Prema G Vasudev; Srinivasarao Raghothama; Chandrasekharan Ramakrishnan; Narayanaswamy Shamala; Padmanabhan Balaram
Journal:  J Am Chem Soc       Date:  2009-04-29       Impact factor: 15.419
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  8 in total

1.  Heterogeneous H-bonding in a foldamer helix.

Authors:  Brian F Fisher; Li Guo; Brian S Dolinar; Ilia A Guzei; Samuel H Gellman
Journal:  J Am Chem Soc       Date:  2015-05-14       Impact factor: 15.419

2.  Structural mimicry of the α-helix in aqueous solution with an isoatomic α/β/γ-peptide backbone.

Authors:  Tomohisa Sawada; Samuel H Gellman
Journal:  J Am Chem Soc       Date:  2011-04-26       Impact factor: 15.419

3.  Environmental Modulation of Chiral Prolinamide Catalysts for Stereodivergent Conjugate Addition.

Authors:  Xiaowei Li; Yan Zhao
Journal:  J Catal       Date:  2022-01-10       Impact factor: 7.920

4.  Impact of γ-Amino Acid Residue Preorganization on α/γ-Peptide Foldamer Helicity in Aqueous Solution.

Authors:  Brian F Fisher; Samuel H Gellman
Journal:  J Am Chem Soc       Date:  2016-08-16       Impact factor: 15.419

5.  Differential impact of β and γ residue preorganization on α/β/γ-peptide helix stability in water.

Authors:  Young-Hee Shin; David E Mortenson; Kenneth A Satyshur; Katrina T Forest; Samuel H Gellman
Journal:  J Am Chem Soc       Date:  2013-05-23       Impact factor: 15.419

6.  New preorganized γ-amino acids as foldamer building blocks.

Authors:  Li Guo; Weicheng Zhang; Ilia A Guzei; Lara C Spencer; Samuel H Gellman
Journal:  Org Lett       Date:  2012-05-08       Impact factor: 6.005

7.  Evaluation of a cyclopentane-based γ-amino acid for the ability to promote α/γ-peptide secondary structure.

Authors:  Michael W Giuliano; Stacy J Maynard; Aaron M Almeida; Andrew G Reidenbach; Li Guo; Emily C Ulrich; Ilia A Guzei; Samuel H Gellman
Journal:  J Org Chem       Date:  2013-12-05       Impact factor: 4.354

8.  α,ε-Hybrid Peptide Foldamers: Self-Assembly of Peptide with Trans Carbon-Carbon Double Bonds in the Backbone and Its Saturated Analogue.

Authors:  Mintu Debnath; Tanmay Das; Debasish Podder; Debasish Haldar
Journal:  ACS Omega       Date:  2018-08-08
  8 in total

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