Supramolecular catalysis by recognition-encoded oligomers: discovery of a synthetic imine polymerase.

Chemical Science
Luca Gabrielli, Christopher A Hunter

Abstract

All key chemical transformations in biology are catalysed by linear oligomers. Catalytic properties could be programmed into synthetic oligomers in the same way as they are programmed into proteins, and an example of the discovery of emergent catalytic properties in a synthetic oligomer is reported. Dynamic combinatorial chemistry experiments designed to study the templating of a recognition-encoded oligomer by the complementary sequence have uncovered an unexpected imine polymerase activity. Libraries of equilibrating imines were formed by coupling diamine linkers with monomer building blocks composed of dialdehydes functionalised with either a trifluoromethyl phenol (D) or phosphine oxide (A) H-bond recognition unit. However, addition of the AAA trimer to a mixture of the phenol dialdehyde and the diamine linker did not template the formation of the DDD oligo-imine. Instead, AAA was found to be a catalyst, leading to rapid formation of long oligomers of D. AAA catalysed a number of different imine formation reactions, but a complementary phenol recognition group on the aldehyde reaction partner is an essential requirement. Competitive inhibition by an unreactive phenol confirmed the role of H-bonding in substrate recognition....Continue Reading

References

Aug 30, 1990·Nature·A D Ellington, J W Szostak
Aug 17, 1995·Nature·C BöhlerL E Orgel
Mar 18, 1997·Proceedings of the National Academy of Sciences of the United States of America·I Huc, J M Lehn
Dec 12, 1997·Origins of Life and Evolution of the Biosphere : the Journal of the International Society for the Study of the Origin of Life·A Eschenmoser
Jun 15, 1993·Proceedings of the National Academy of Sciences of the United States of America·R KramerA Marquis-Rigault
Jan 31, 2002·Journal of the American Chemical Society·Xiaoyu LiDavid G Lynn
Dec 20, 2002·Angewandte Chemie·Stuart J RowanJ Fraser Stoddart
Nov 1, 2003·Science·Haibo LiuEric T Kool
Nov 13, 2003·Journal of the American Chemical Society·Daniel M Rosenbaum, David R Liu
Mar 24, 2005·Journal of the American Chemical Society·Lilu ZhangEric Meggers
May 19, 2005·Angewandte Chemie·Yoshie TanakaEiji Yashima
Sep 14, 2006·Chemical Reviews·Peter T CorbettSijbren Otto
Aug 30, 2008·The Journal of Organic Chemistry·Ryo AmemiyaMasahiko Yamaguchi
Oct 1, 2008·Journal of the American Chemical Society·Hiroshi ItoEiji Yashima
May 16, 2009·Angewandte Chemie·James C DelaneyEric T Kool
Nov 3, 2009·Current Opinion in Chemical Biology·Daniel H Appella
Dec 1, 1994·The Journal of Organic Chemistry·Barbara A Schweitzer, Eric T Kool
Jul 12, 2011·Angewandte Chemie·Yoshinori TakashimaAkira Harada
Sep 21, 2011·Philosophical Transactions of the Royal Society of London. Series B, Biological Sciences·David M J Lilley
Apr 25, 2013·Chemistry : a European Journal·Anna-Barbara Gerber, Christian J Leumann
May 13, 2015·Journal of the American Chemical Society·Liqin ZhangSteven A Benner
Apr 30, 2017·Chemical Science·Diego Núñez-Villanueva, Christopher A Hunter
May 5, 2017·Journal of the American Chemical Society·Diego Núñez-VillanuevaChristopher A Hunter
Sep 1, 2017·Journal of the American Chemical Society·Alexander E StrossChristopher A Hunter
Mar 1, 2016·Chemical Science·Giulia IadevaiaChristopher A Hunter
Mar 7, 2018·Nature Chemistry·Zhen ChenDavid R Liu
Mar 17, 2018·Journal of the American Chemical Society·Prakash ChandraAntony E Fernandes
Jan 1, 2016·Chemical Science·Alexander E StrossChristopher A Hunter
Sep 1, 2016·Chemical Science·Alexander E StrossChristopher A Hunter
Sep 5, 2018·Journal of the American Chemical Society·Jonathan A SwainChristopher A Hunter
Mar 13, 2019·Angewandte Chemie·Jason Y C LimCharlotte K Williams
Mar 19, 2019·Chemical Science·Filip T Szczypiński, Christopher A Hunter
Mar 25, 2020·Chemical Science·Luca GabrielliChristopher A Hunter

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Citations

Jun 4, 2021·Journal of the American Chemical Society·Pavle TroseljChristopher A Hunter
Aug 12, 2021·Chemical Science·Giulia IadevaiaChristopher A Hunter
Oct 9, 2021·Organic & Biomolecular Chemistry·Daniele Rosa-GastaldoLuca Gabrielli

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