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A multifunctional surfactant catalyst inspired by hydrolases

The remarkable power of enzymes to undertake catalysis frequently stems from their grouping of multiple, complementary chemical units within close proximity around the enzyme active site. Motivated by this, we report here a bioinspired surfactant catalyst that incorporates a variety of chemical func...

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Detalles Bibliográficos
Autores principales: Nothling, Mitchell D., Xiao, Zeyun, Hill, Nicholas S., Blyth, Mitchell T., Bhaskaran, Ayana, Sani, Marc-Antoine, Espinosa-Gomez, Andrea, Ngov, Kevin, White, Jonathan, Buscher, Tim, Separovic, Frances, O’Mara, Megan L., Coote, Michelle L., Connal, Luke A.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Association for the Advancement of Science 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7112759/
https://www.ncbi.nlm.nih.gov/pubmed/32270041
http://dx.doi.org/10.1126/sciadv.aaz0404
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author Nothling, Mitchell D.
Xiao, Zeyun
Hill, Nicholas S.
Blyth, Mitchell T.
Bhaskaran, Ayana
Sani, Marc-Antoine
Espinosa-Gomez, Andrea
Ngov, Kevin
White, Jonathan
Buscher, Tim
Separovic, Frances
O’Mara, Megan L.
Coote, Michelle L.
Connal, Luke A.
author_facet Nothling, Mitchell D.
Xiao, Zeyun
Hill, Nicholas S.
Blyth, Mitchell T.
Bhaskaran, Ayana
Sani, Marc-Antoine
Espinosa-Gomez, Andrea
Ngov, Kevin
White, Jonathan
Buscher, Tim
Separovic, Frances
O’Mara, Megan L.
Coote, Michelle L.
Connal, Luke A.
author_sort Nothling, Mitchell D.
collection PubMed
description The remarkable power of enzymes to undertake catalysis frequently stems from their grouping of multiple, complementary chemical units within close proximity around the enzyme active site. Motivated by this, we report here a bioinspired surfactant catalyst that incorporates a variety of chemical functionalities common to hydrolytic enzymes. The textbook hydrolase active site, the catalytic triad, is modeled by positioning the three groups of the triad (-OH, -imidazole, and -CO(2)H) on a single, trifunctional surfactant molecule. To support this, we recreate the hydrogen bond donating arrangement of the oxyanion hole by imparting surfactant functionality to a guanidinium headgroup. Self-assembly of these amphiphiles in solution drives the collection of functional headgroups into close proximity around a hydrophobic nano-environment, affording hydrolysis of a model ester at rates that challenge α-chymotrypsin. Structural assessment via NMR and XRD, paired with MD simulation and QM calculation, reveals marked similarities of the co-micelle catalyst to native enzymes.
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spelling pubmed-71127592020-04-08 A multifunctional surfactant catalyst inspired by hydrolases Nothling, Mitchell D. Xiao, Zeyun Hill, Nicholas S. Blyth, Mitchell T. Bhaskaran, Ayana Sani, Marc-Antoine Espinosa-Gomez, Andrea Ngov, Kevin White, Jonathan Buscher, Tim Separovic, Frances O’Mara, Megan L. Coote, Michelle L. Connal, Luke A. Sci Adv Research Articles The remarkable power of enzymes to undertake catalysis frequently stems from their grouping of multiple, complementary chemical units within close proximity around the enzyme active site. Motivated by this, we report here a bioinspired surfactant catalyst that incorporates a variety of chemical functionalities common to hydrolytic enzymes. The textbook hydrolase active site, the catalytic triad, is modeled by positioning the three groups of the triad (-OH, -imidazole, and -CO(2)H) on a single, trifunctional surfactant molecule. To support this, we recreate the hydrogen bond donating arrangement of the oxyanion hole by imparting surfactant functionality to a guanidinium headgroup. Self-assembly of these amphiphiles in solution drives the collection of functional headgroups into close proximity around a hydrophobic nano-environment, affording hydrolysis of a model ester at rates that challenge α-chymotrypsin. Structural assessment via NMR and XRD, paired with MD simulation and QM calculation, reveals marked similarities of the co-micelle catalyst to native enzymes. American Association for the Advancement of Science 2020-04-01 /pmc/articles/PMC7112759/ /pubmed/32270041 http://dx.doi.org/10.1126/sciadv.aaz0404 Text en Copyright © 2020 The Authors, some rights reserved; exclusive licensee American Association for the Advancement of Science. No claim to original U.S. Government Works. Distributed under a Creative Commons Attribution NonCommercial License 4.0 (CC BY-NC). http://creativecommons.org/licenses/by-nc/4.0/ This is an open-access article distributed under the terms of the Creative Commons Attribution-NonCommercial license (http://creativecommons.org/licenses/by-nc/4.0/) , which permits use, distribution, and reproduction in any medium, so long as the resultant use is not for commercial advantage and provided the original work is properly cited.
spellingShingle Research Articles
Nothling, Mitchell D.
Xiao, Zeyun
Hill, Nicholas S.
Blyth, Mitchell T.
Bhaskaran, Ayana
Sani, Marc-Antoine
Espinosa-Gomez, Andrea
Ngov, Kevin
White, Jonathan
Buscher, Tim
Separovic, Frances
O’Mara, Megan L.
Coote, Michelle L.
Connal, Luke A.
A multifunctional surfactant catalyst inspired by hydrolases
title A multifunctional surfactant catalyst inspired by hydrolases
title_full A multifunctional surfactant catalyst inspired by hydrolases
title_fullStr A multifunctional surfactant catalyst inspired by hydrolases
title_full_unstemmed A multifunctional surfactant catalyst inspired by hydrolases
title_short A multifunctional surfactant catalyst inspired by hydrolases
title_sort multifunctional surfactant catalyst inspired by hydrolases
topic Research Articles
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7112759/
https://www.ncbi.nlm.nih.gov/pubmed/32270041
http://dx.doi.org/10.1126/sciadv.aaz0404
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