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The search for new amphiphiles: synthesis of a modular, high-throughput library

Amphiphilic compounds are used in a variety of applications due to their lyotropic liquid-crystalline phase formation, however only a limited number of compounds, in a potentially limitless field, are currently in use. A library of organic amphiphilic compounds was synthesised consisting of glucose,...

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Autores principales: Feast, George C, Lepitre, Thomas, Mulet, Xavier, Conn, Charlotte E, Hutt, Oliver E, Savage, G Paul, Drummond, Calum J
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2014
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4142986/
https://www.ncbi.nlm.nih.gov/pubmed/25161714
http://dx.doi.org/10.3762/bjoc.10.163
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author Feast, George C
Lepitre, Thomas
Mulet, Xavier
Conn, Charlotte E
Hutt, Oliver E
Savage, G Paul
Drummond, Calum J
author_facet Feast, George C
Lepitre, Thomas
Mulet, Xavier
Conn, Charlotte E
Hutt, Oliver E
Savage, G Paul
Drummond, Calum J
author_sort Feast, George C
collection PubMed
description Amphiphilic compounds are used in a variety of applications due to their lyotropic liquid-crystalline phase formation, however only a limited number of compounds, in a potentially limitless field, are currently in use. A library of organic amphiphilic compounds was synthesised consisting of glucose, galactose, lactose, xylose and mannose head groups and double and triple-chain hydrophobic tails. A modular, high-throughput approach was developed, whereby head and tail components were conjugated using the copper-catalysed azide–alkyne cycloaddition (CuAAC) reaction. The tails were synthesised from two core alkyne-tethered intermediates, which were subsequently functionalised with hydrocarbon chains varying in length and degree of unsaturation and branching, while the five sugar head groups were selected with ranging substitution patterns and anomeric linkages. A library of 80 amphiphiles was subsequently produced, using a 24-vial array, with the majority formed in very good to excellent yields. A preliminary assessment of the liquid-crystalline phase behaviour is also presented.
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spelling pubmed-41429862014-08-26 The search for new amphiphiles: synthesis of a modular, high-throughput library Feast, George C Lepitre, Thomas Mulet, Xavier Conn, Charlotte E Hutt, Oliver E Savage, G Paul Drummond, Calum J Beilstein J Org Chem Full Research Paper Amphiphilic compounds are used in a variety of applications due to their lyotropic liquid-crystalline phase formation, however only a limited number of compounds, in a potentially limitless field, are currently in use. A library of organic amphiphilic compounds was synthesised consisting of glucose, galactose, lactose, xylose and mannose head groups and double and triple-chain hydrophobic tails. A modular, high-throughput approach was developed, whereby head and tail components were conjugated using the copper-catalysed azide–alkyne cycloaddition (CuAAC) reaction. The tails were synthesised from two core alkyne-tethered intermediates, which were subsequently functionalised with hydrocarbon chains varying in length and degree of unsaturation and branching, while the five sugar head groups were selected with ranging substitution patterns and anomeric linkages. A library of 80 amphiphiles was subsequently produced, using a 24-vial array, with the majority formed in very good to excellent yields. A preliminary assessment of the liquid-crystalline phase behaviour is also presented. Beilstein-Institut 2014-07-10 /pmc/articles/PMC4142986/ /pubmed/25161714 http://dx.doi.org/10.3762/bjoc.10.163 Text en Copyright © 2014, Feast et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Feast, George C
Lepitre, Thomas
Mulet, Xavier
Conn, Charlotte E
Hutt, Oliver E
Savage, G Paul
Drummond, Calum J
The search for new amphiphiles: synthesis of a modular, high-throughput library
title The search for new amphiphiles: synthesis of a modular, high-throughput library
title_full The search for new amphiphiles: synthesis of a modular, high-throughput library
title_fullStr The search for new amphiphiles: synthesis of a modular, high-throughput library
title_full_unstemmed The search for new amphiphiles: synthesis of a modular, high-throughput library
title_short The search for new amphiphiles: synthesis of a modular, high-throughput library
title_sort search for new amphiphiles: synthesis of a modular, high-throughput library
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4142986/
https://www.ncbi.nlm.nih.gov/pubmed/25161714
http://dx.doi.org/10.3762/bjoc.10.163
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