Literature DB >> 22024881

Chiral information harvesting in dendritic metallopeptides.

Naoki Ousaka1, Yuki Takeyama, Hiroki Iida, Eiji Yashima.   

Abstract

Long-range communication of stereochemical information is common in biological systems, particularly in enzyme-catalysed reactions. Here, we report the remote control of the dynamic chirality of metal centres, coordinated by 2,2'-bipyridine ligands bearing dynamic helical oligopeptides. The helical chirality of the oligopeptides is controlled by a stereocentre remote from the metal. We show that when a mixture of chiral and achiral peptide ligands is used, both the chirality of the metal centre and that of the achiral oligopeptide helices are significantly amplified. The amplification mechanism relies on several steps of chirality induction, first from a single chiral peptide to the helicity of an oligopeptide through the induction of propeller chirality at the metal centre, then on to induction of helical chirality in an achiral oligopeptide.

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Year:  2011        PMID: 22024881     DOI: 10.1038/nchem.1146

Source DB:  PubMed          Journal:  Nat Chem        ISSN: 1755-4330            Impact factor:   24.427


  28 in total

Review 1.  Chiral architectures from macromolecular building blocks.

Authors:  J J Cornelissen; A E Rowan; R J Nolte; N A Sommerdijk
Journal:  Chem Rev       Date:  2001-12       Impact factor: 60.622

Review 2.  "Let's twist again"--double-stranded, triple-stranded, and circular helicates.

Authors:  M Albrecht
Journal:  Chem Rev       Date:  2001-11       Impact factor: 60.622

3.  Chiral induction in a ribose-decorated metallostar through intrinsic and interionic diastereomeric interactions.

Authors:  Edwin C Constable; Richard Frantz; Catherine E Housecroft; Jérôme Lacour; Azad Mahmood
Journal:  Inorg Chem       Date:  2004-08-09       Impact factor: 5.165

Review 4.  Supramolecular chirality of self-assembled systems in solution.

Authors:  Miguel A Mateos-Timoneda; Mercedes Crego-Calama; David N Reinhoudt
Journal:  Chem Soc Rev       Date:  2004-07-06       Impact factor: 54.564

5.  Chiral induction in quinoline-derived oligoamide foldamers: assignment of helical handedness and role of steric effects.

Authors:  Christel Dolain; Hua Jiang; Jean-Michel Léger; Philippe Guionneau; Ivan Huc
Journal:  J Am Chem Soc       Date:  2005-09-21       Impact factor: 15.419

6.  Control of helix sense in protein-mimicking backbone by the noncovalent chiral effect.

Authors:  Yoshihito Inai; Hisatoshi Komori; Naoki Ousaka
Journal:  Chem Rec       Date:  2007       Impact factor: 6.771

7.  Proton magnetic resonance line broadening produced by association with a nitroxide radical in studies of amide and peptide conformation.

Authors:  K D Kopple; T J Schamper
Journal:  J Am Chem Soc       Date:  1972-05-17       Impact factor: 15.419

8.  Noncovalent domino effect on helical screw sense of chiral peptides possessing C-terminal chiral residue.

Authors:  Yoshihito Inai; Yuya Ishida; Kenichi Tagawa; Akinori Takasu; Tadamichi Hirabayashi
Journal:  J Am Chem Soc       Date:  2002-03-20       Impact factor: 15.419

9.  Mechanism for the noncovalent chiral domino effect: new paradigm for the chiral role of the N-terminal segment in a 3(10)-helix.

Authors:  Yoshihito Inai; Naoki Ousaka; Takahiro Okabe
Journal:  J Am Chem Soc       Date:  2003-07-09       Impact factor: 15.419

10.  Transfer of noncovalent chiral information along an optically inactive helical peptide chain: allosteric control of asymmetry of the C-terminal site by external molecule that binds to the N-terminal site.

Authors:  Naoki Ousaka; Yoshihito Inai
Journal:  J Org Chem       Date:  2009-02-20       Impact factor: 4.354

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  11 in total

1.  Molecular devices: Communicating chirality.

Authors:  Jonathan Clayden
Journal:  Nat Chem       Date:  2011-10-24       Impact factor: 24.427

2.  Dynamic control of chirality and self-assembly of double-stranded helicates with light.

Authors:  Depeng Zhao; Thomas van Leeuwen; Jinling Cheng; Ben L Feringa
Journal:  Nat Chem       Date:  2016-11-07       Impact factor: 24.427

3.  End-to-end conformational communication through a synthetic purinergic receptor by ligand-induced helicity switching.

Authors:  Robert A Brown; Vincent Diemer; Simon J Webb; Jonathan Clayden
Journal:  Nat Chem       Date:  2013-09-15       Impact factor: 24.427

4.  Anion-coordination-driven single-double helix switching and chiroptical molecular switching based on oligoureas.

Authors:  Hongfei Li; Lei Kou; Lin Liang; Boyang Li; Wei Zhao; Xiao-Juan Yang; Biao Wu
Journal:  Chem Sci       Date:  2022-04-07       Impact factor: 9.969

5.  Hierarchical communication of chirality for aromatic oligoamide sequences.

Authors:  Jiajia Zhang; Dan Luo; Chunmiao Ma; Lu Huang; Quan Gan
Journal:  Nat Commun       Date:  2021-05-11       Impact factor: 14.919

6.  A tendril perversion in a helical oligomer: trapping and characterizing a mobile screw-sense reversal.

Authors:  Michael Tomsett; Irene Maffucci; Bryden A F Le Bailly; Liam Byrne; Stefan M Bijvoets; M Giovanna Lizio; James Raftery; Craig P Butts; Simon J Webb; Alessandro Contini; Jonathan Clayden
Journal:  Chem Sci       Date:  2017-01-25       Impact factor: 9.825

7.  Flaws in foldamers: conformational uniformity and signal decay in achiral helical peptide oligomers.

Authors:  Bryden A F Le Bailly; Liam Byrne; Vincent Diemer; Mohammadali Foroozandeh; Gareth A Morris; Jonathan Clayden
Journal:  Chem Sci       Date:  2015-01-21       Impact factor: 9.825

8.  Helicity-driven chiral self-sorting supramolecular polymerization with Ag+: right- and left-helical aggregates.

Authors:  Mirae Ok; Ka Young Kim; Heekyoung Choi; Seonghan Kim; Shim Sung Lee; Jaeheung Cho; Sung Ho Jung; Jong Hwa Jung
Journal:  Chem Sci       Date:  2022-02-09       Impact factor: 9.825

9.  Conformational Switching of a Foldamer in a Multicomponent System by pH-Filtered Selection between Competing Noncovalent Interactions.

Authors:  Julien Brioche; Sarah J Pike; Sofja Tshepelevitsh; Ivo Leito; Gareth A Morris; Simon J Webb; Jonathan Clayden
Journal:  J Am Chem Soc       Date:  2015-05-14       Impact factor: 15.419

10.  Refoldable Foldamers: Global Conformational Switching by Deletion or Insertion of a Single Hydrogen Bond.

Authors:  Bryden A F Le Bailly; Liam Byrne; Jonathan Clayden
Journal:  Angew Chem Int Ed Engl       Date:  2016-01-14       Impact factor: 15.336

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