Kinetics of helix-handedness inversion: folding and unfolding in aromatic amide oligomers

Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry
Nicolas DelsucIvan Huc

Abstract

A series of helically folded oligoamides of 8-amino-2-quinoline carboxylic acid possessing 6, 7, 8, 9, 10 or 16 units are prepared following convergent synthetic schemes. The right-handed (P) and the left-handed (M) helical conformers of these oligomers undergo an exchange slow enough to allow their chromatographic separation on a chiral stationary phase. Thus, the M conformer is isolated for each of these oligomers and its slow racemization in hexane/CHCl(3) solutions is monitored at various temperatures using chiral HPLC. The kinetics of racemization at different temperatures in hexane/CHCl(3) (75:25 vol/vol) are fitted to a first order kinetic model to yield the kinetic constant and the Gibbs energy of activation for oligomers having 6, 7, 8, 9, 10 or 16 quinoline units. This energy gives the first quantitative measure of the exceptional stability of the helical conformers of an aromatic amide foldamer with respect to its partly unfolded conformations that occur between an M helix and a P helix. The trend of the Gibbs energy as a function of oligomer length suggests that helix-handedness inversion does not require a complete unfolding of a helical strand and may instead occur through the propagation of a local unfolding sepa...Continue Reading

References

Nov 11, 1999·Angewandte Chemie·M M GreenJ V Selinger
Oct 6, 2000·Journal of Molecular Graphics & Modelling·N H MartinJ C Moore
Nov 7, 2001·Chemistry : a European Journal·B Gong
Dec 13, 2001·Chemical Reviews·D J HillJ S Moore
Aug 15, 2002·Proceedings of the National Academy of Sciences of the United States of America·Bing GongLihua Yua
Mar 20, 2003·Journal of the American Chemical Society·Hua JiangIvan Huc
Jul 25, 2003·Journal of Chromatography. a·J KrupcikW Armstrong
Jan 30, 2004·Journal of the American Chemical Society·Hua JiangIvan Huc
Aug 12, 2004·Journal of the American Chemical Society·Victor MaurizotIvan Huc
Sep 30, 2004·Journal of the American Chemical Society·Jun-Li HouZhan-Ting Li
Feb 24, 2005·Angewandte Chemie·Joachim GarricIvan Huc
Jun 7, 2005·Chembiochem : a European Journal of Chemical Biology·Matthew Kubasik, Adam Blom
Aug 3, 2005·Chemistry : a European Journal·Christel DolainIvan Huc
Nov 1, 2005·Proceedings of the National Academy of Sciences of the United States of America·Christel DolainIvan Huc
Jan 18, 2006·Accounts of Chemical Research·Matthew T StoneJeffrey S Moore
Oct 10, 2006·The Journal of Organic Chemistry·Elizabeth R GilliesIvan Huc
Oct 20, 2006·Angewandte Chemie·Nicolas DelsucIvan Huc
Nov 17, 2006·The Journal of Physical Chemistry. B·J SchmidtD Sebastiani
Apr 7, 2007·Organic Letters·Chuang LiRen-Xiao Wang
Apr 18, 2007·Nature Chemical Biology·Catherine M GoodmanWilliam F DeGrado
Apr 19, 2007·Chemistry, an Asian Journal·Zhan-Ting LiHui-Ping Yi
Jul 31, 2007·Chemistry : a European Journal·Emanuela BerniIvan Huc
Aug 1, 2007·Chemistry : a European Journal·Joachim GarricIvan Huc
Dec 18, 2007·Journal of the American Chemical Society·Naoki OusakaReiko Kuroda

❮ Previous
Next ❯

Citations

Aug 9, 2012·Chemical Reviews·Dan-Wei ZhangZhan-Ting Li
Jun 20, 2012·Journal of the American Chemical Society·Shinji AndoTakuzo Aida
Jun 14, 2012·Journal of the American Chemical Society·Yann FerrandIvan Huc
Sep 7, 2012·Journal of the American Chemical Society·Quan GanIvan Huc
Jun 15, 2013·Journal of the American Chemical Society·Mayumi KudoIvan Huc
Apr 2, 2009·Journal of the American Chemical Society·Martin WolffsAlbertus P H J Schenning
Jun 18, 2009·Journal of the American Chemical Society·David Sánchez-GarcíaIvan Huc
Jul 23, 2014·Chemical Communications : Chem Comm·Mayumi KudoIvan Huc
Apr 26, 2012·Chemical Communications : Chem Comm·Ting QiIvan Huc
Feb 18, 2016·Chemical Communications : Chem Comm·Jee Seon KimKyu-Sung Jeong
Feb 15, 2016·Journal of Chromatography. a·Hiroki NoguchiHirotaka Ihara
Oct 29, 2015·Chemical Communications : Chem Comm·Ara M AbramyanVojislava Pophristic
Mar 10, 2016·Accounts of Chemical Research·C Scott Hartley
Dec 3, 2011·Angewandte Chemie·Laurence DelaurièreIvan Huc
Jul 29, 2010·Chembiochem : a European Journal of Chemical Biology·Jone Iriondo-AlberdiIvan Huc
Jul 1, 2011·Angewandte Chemie·Yann FerrandIvan Huc
Feb 7, 2015·Chemistry : a European Journal·Abdulselam Adam, Gebhard Haberhauer
May 20, 2015·Chemistry : a European Journal·Dhayalan Balamurugan, Kannoth M Muraleedharan
Jan 26, 2016·Chembiochem : a European Journal of Chemical Biology·Michal JewginskiCameron David Mackereth
Dec 22, 2009·Physical Chemistry Chemical Physics : PCCP·Rubén D Parra
Dec 18, 2013·Organic & Biomolecular Chemistry·Matteo De Poli, Jonathan Clayden
Nov 29, 2014·Chemical Communications : Chem Comm·Rumi TamotoReiko Oda
Sep 23, 2016·The Journal of Physical Chemistry. B·Lalita UribeGregor Diezemann
Sep 23, 2016·Journal of the American Chemical Society·Xuesong LiIvan Huc
Mar 21, 2018·Nature Chemistry·Joseph M RogersIvan Huc
Apr 26, 2016·Nature Communications·Sunil KumarAndrew D Miranker
May 29, 2020·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Hidetomo YokooYosuke Demizu
May 13, 2021·Nature Communications·Jiajia ZhangQuan Gan
Feb 11, 2011·Journal of the American Chemical Society·Nicolas DelsucIvan Huc
Oct 16, 2010·The Journal of Organic Chemistry·Benoît BaptisteIvan Huc
Dec 15, 2010·The Journal of Organic Chemistry·Amol M KendhaleIvan Huc
Oct 12, 2017·The Journal of Physical Chemistry. B·Dongbo ZhaoShuhua Li
Dec 25, 2019·Journal of the American Chemical Society·Jingwei YinVladimir B Birman

❮ Previous
Next ❯

Related Concepts

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.

Related Papers

Proceedings of the National Academy of Sciences of the United States of America
Gregory N TewWilliam F DeGrado
© 2022 Meta ULC. All rights reserved