The third orthogonal dynamic covalent bond

Chemical Science
Santiago LascanoStefan Matile

Abstract

Orthogonal dynamic covalent bonds are of interest for the construction of functional systems. The orthogonality of disulfide and hydrazone exchange under basic and acidic conditions, respectively, is well established. However, the integration of boronate esters as the third bond has failed so far because they exchanged too easily, especially under hydrazone exchange conditions. In this report, a collection of bioinspired catechols derived from adhesive natural products from cyanobacteria is screened with phenylboronic acids with proximal alcohols (benzoboroxoles), amines and fluorines to identify the least labile boronate esters. Moreover, Kool's 2-aminophenol catalysts are introduced to selectively accelerate hydrazone exchange without disturbing sufficiently inert boronate esters. Based on these results, we identified three different conditions to selectively exchange disulfides, hydrazones and boronate esters, that is to demonstrate the existence of three orthogonal dynamic covalent bonds. Moreover, their compatibility with functional systems is confirmed by successful hydrazone exchange in multicomponent surface architectures in the presence of intact boronate esters and disulfides.

References

Dec 20, 2002·Angewandte Chemie·Stuart J RowanJ Fraser Stoddart
May 15, 2003·Chemical Communications : Chem Comm·Régis Nguyen, Ivan Huc
Apr 1, 2004·Chemistry : a European Journal·Olof RamströmJean-Marie Lehn
Jan 26, 2006·Journal of the American Chemical Society·Stefan ZürcherKarl Gademann
Feb 14, 2006·Organic Letters·Yolanda Pérez-FuertesTony D James
Dec 7, 2006·Journal of the American Chemical Society·Anouk DirksenPhilip E Dawson
Dec 21, 2006·Journal of the American Chemical Society·Weijun NiuJohn J Lavigne
Sep 20, 2007·Chemistry : a European Journal·Rupam J SarmaJonathan R Nitschke
Jan 24, 2008·Angewandte Chemie·Nicolas ChristinatKay Severin
Apr 10, 2008·Journal of the American Chemical Society·Shinya HagiharaStefan Matile
Sep 4, 2008·Journal of the American Chemical Society·Minyong LiBinghe Wang
Nov 6, 2008·Chemical Communications : Chem Comm·A Gastón OrrilloRicardo L E Furlan
Nov 6, 2008·Chemical Communications : Chem Comm·Zaida Rodriguez-Docampo, Sijbren Otto
Oct 19, 2010·Angewandte Chemie·Michael J BarrellDavid A Leigh
Apr 26, 2011·Journal of the American Chemical Society·Mao LiKatsuhiko Ariga
Jun 7, 2011·Chemical Communications : Chem Comm·Sophie R BeerenJeremy K M Sanders
Jun 18, 2011·Journal of the American Chemical Society·Marco ListaStefan Matile
Sep 13, 2011·Chemical Society Reviews·Emilie MoulinNicolas Giuseppone
Jan 21, 2012·Trends in Biotechnology·Adrian G Torres, Michael J Gait
Feb 7, 2012·Journal of the American Chemical Society·Gregory A EllisRonald T Raines
Feb 22, 2013·Bioconjugate Chemistry·Mohammad RashidianMark D Distefano
May 16, 2013·Journal of the American Chemical Society·Araceli G CampañaUrszula Lewandowska
Jun 5, 2013·Journal of the American Chemical Society·Jianwei LiSijbren Otto
Jun 12, 2013·Chemical Society Reviews·Yinghua JinWei Zhang
Jun 28, 2013·Journal of the American Chemical Society·Johannes F TeichertJeffrey W Bode
Jul 19, 2013·Chemical Society Reviews·Xin WuYun-Bao Jiang
Nov 15, 2013·Journal of the American Chemical Society·Eric T KoolPete Crisalli
Nov 30, 2013·Chemical Society Reviews·Adam WilsonStefan Matile
Dec 11, 2013·Bioconjugate Chemistry·Michaela WendelerManuel Baca
Jan 17, 2014·Chemical Society Reviews·Xin Su, Ivan Aprahamian
Mar 29, 2014·Macromolecular Bioscience·David Oupický, Jing Li
Apr 17, 2014·Journal of the American Chemical Society·Giulio GaspariniStefan Matile
May 21, 2014·Macromolecular Rapid Communications·Dipankar BasakSuhrit Ghosh
Jul 17, 2014·Chemical Society Reviews·Salvatore ZarraJonathan R Nitschke
Jul 24, 2014·Chemical Communications : Chem Comm·Nicolas LuisierKay Severin
Dec 23, 2014·Chemical Science·Hyun Hwa JoEric V Anslyn
Jan 7, 2015·Journal of the American Chemical Society·Chang WangSteven L Regen
Jan 20, 2015·Organic & Biomolecular Chemistry·Clare S MahonDavid A Fulton
Feb 27, 2015·Accounts of Chemical Research·Karl Gademann

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Citations

Aug 23, 2018·Chemistry : a European Journal·Lou RocardDavide Bonifazi
Sep 20, 2018·Chemistry : a European Journal·A Gastón OrrilloRicardo L E Furlan
Jan 25, 2017·Macromolecular Rapid Communications·Joe CollinsLuke A Connal
Sep 5, 2018·Nature Chemistry·Wen Jie Ong, Timothy M Swager
Sep 27, 2018·Advanced Science·Shengchang TangKristi S Anseth
Oct 28, 2019·Journal of Materials Chemistry. B, Materials for Biology and Medicine·Lijing TengLi Ren
Oct 8, 2019·Chemical Science·Christopher C Pattillo, Jeffrey S Moore
Sep 30, 2017·Chemistry : a European Journal·Wojciech DrożdżSébastien Ulrich
Dec 6, 2019·Chemical Science·Maitena Martinez-AmezagaRicardo L E Furlan
Jan 19, 2018·Chemistry : a European Journal·A Gastón OrrilloRicardo L E Furlan
Aug 26, 2020·Chemistry : a European Journal·Martin Hähsler, Michael Mastalerz
Jan 16, 2021·Chemical Communications : Chem Comm·Daniel CarbajoIgnacio Alfonso
Apr 28, 2021·Organic Letters·Wojciech DrożdżArtur R Stefankiewicz
May 15, 2021·Advanced Healthcare Materials·Muhammad RizwanMolly S Shoichet
May 27, 2021·Bioorganic Chemistry·Mayte A Martínez-AguirreAnatoly K Yatsimirsky
Jun 5, 2021·Angewandte Chemie·Tanausú SantosRomen Carrillo
Nov 23, 2018·Journal of the American Chemical Society·Anna J McConnellJonathan R Nitschke
Dec 21, 2016·Biomacromolecules·Emma R L BrissonLuke A Connal
Aug 16, 2016·Journal of the American Chemical Society·Helen M SeifertEric V Anslyn
Apr 26, 2017·Journal of the American Chemical Society·Bartosz M MatysiakSijbren Otto
Jun 24, 2017·Accounts of Chemical Research·Jean SeptavauxJulien Leclaire
Jan 5, 2017·Journal of the American Chemical Society·Irene GeorgiouDavide Bonifazi
Jun 24, 2017·Chemical Reviews·Dominik K Kölmel, Eric T Kool
Jul 28, 2017·Journal of the American Chemical Society·Ivica CvrtilaSijbren Otto

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