Literature DB >> 20518572

Design, synthesis, and structural analysis of D,L-mixed polypyrrolinones. 2. Macrocyclic hexapyrrolinones.

Amos B Smith1, Hui Xiong, Adam K Charnley, Meinrad Brenner, Eugen F Mesaros, Craig S Kenesky, Luigi Di Costanzo, David W Christianson, Ralph Hirschmann.   

Abstract

The design, synthesis, and structural analysis of two macrocyclic D,L-alternating hexapyrrolinones have been achieved. These cyclic peptide mimics adopt a flat, hexagonal conformation, stabilized by intramolecular hydrogen bonding between adjacent pyrrolinone rings. Extensive NMR studies and X-ray analysis reveal, respectively, that the macrocyclic hexapyrrolinones aggregate in solution and in the solid state form staggered stacked nanotube-like assemblies.

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Year:  2010        PMID： 20518572      PMCID： PMC2892552          DOI： 10.1021/ol101008y

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  8 in total

1.  Self-Assembling Organic Nanotubes.

Authors:  Dennis T. Bong; Thomas D. Clark; Juan R. Granja; M. Reza Ghadiri
Journal:  Angew Chem Int Ed Engl       Date:  2001-03-16       Impact factor: 15.336

2.  Design, synthesis, and evaluation of a pyrrolinone-based matrix metalloprotease inhibitor.

Authors:  A B Smith; T Nittoli; P A Sprengeler; J J Duan; R Q Liu; R F Hirschmann
Journal:  Org Lett       Date:  2000-11-30       Impact factor: 6.005

3.  Design, synthesis, and biological evaluation of monopyrrolinone-based HIV-1 protease inhibitors possessing augmented P2' side chains.

Authors:  Amos B Smith; Adam K Charnley; Hironori Harada; Jason J Beiger; Louis-David Cantin; Craig S Kenesky; Ralph Hirschmann; Sanjeev Munshi; David B Olsen; Mark W Stahlhut; William A Schleif; Lawrence C Kuo
Journal:  Bioorg Med Chem Lett       Date:  2005-11-18       Impact factor: 2.823

4.  Control of duplex formation and columnar self-assembly with heterogeneous amide/urea macrocycles.

Authors:  Lucile Fischer; Marion Decossas; Jean-Paul Briand; Claude Didierjean; Gilles Guichard
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

5.  Self-assembling organic nanotubes based on a cyclic peptide architecture.

Authors:  M R Ghadiri; J R Granja; R A Milligan; D E McRee; N Khazanovich
Journal:  Nature       Date:  1993-11-25       Impact factor: 49.962

6.  Design, synthesis, and binding affinities of pyrrolinone-based somatostatin mimetics.

Authors:  Amos B Smith; Adam K Charnley; Eugen F Mesaros; Osamu Kikuchi; Wenyong Wang; Andrew Benowitz; Chi-Lien Chu; Jin-Jye Feng; Kuo-Hsin Chen; Atsui Lin; Fong-Chi Cheng; Laurie Taylor; Ralph Hirschmann
Journal:  Org Lett       Date:  2005-02-03       Impact factor: 6.005

7.  Design, synthesis, and biological evaluation of monopyrrolinone-based HIV-1 protease inhibitors.

Authors:  Amos B Smith; Louis-David Cantin; Alexander Pasternak; Lisa Guise-Zawacki; Wenquin Yao; Adam K Charnley; Joseph Barbosa; Paul A Sprengeler; Ralph Hirschmann; Sanjeev Munshi; David B Olsen; William A Schleif; Lawrence C Kuo
Journal:  J Med Chem       Date:  2003-05-08       Impact factor: 7.446

8.  Design and synthesis of nonpeptide peptidomimetic inhibitors of renin.

Authors:  A B Smith; R Akaishi; D R Jones; T P Keenan; M C Guzman; R C Holcomb; P A Sprengeler; J L Wood; R Hirschmann; M K Holloway
Journal:  Biopolymers       Date:  1995       Impact factor: 2.505
  8 in total
  1 in total

1.  Pyrrolinone-based peptidomimetics. "Let the enzyme or receptor be the judge".

Authors:  Amos B Smith; Adam K Charnley; Ralph Hirschmann
Journal:  Acc Chem Res       Date:  2010-12-22       Impact factor: 22.384
  1 in total

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