Self-organizing behaviour of glycosteroidal bolaphiles: insights into lipidic microsegregation

R. Xu; F. Ali-Rachedi; N. M. Xavier; S. Chambert; F. Ferkous; Y. Queneau; S. J. Cowling; E. J. Davis; J. W. Goodby

doi:10.1039/C4OB02191F

Self-organizing behaviour of glycosteroidal bolaphiles: insights into lipidic microsegregation†

R. Xu,^ab F. Ali-Rachedi,^abcd N. M. Xavier,^abe S. Chambert,^ab F. Ferkous,^cd Y. Queneau,*^ab S. J. Cowling,*^f E. J. Davis^f and J. W. Goodby^f

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* Corresponding authors

^a INSA Lyon, ICBMS, Bâtiment J. Verne, 20 av A. Einstein, F 69621 Villeurbanne, France
E-mail: yves.queneau@insa-lyon.fr

^b CNRS, UMR 5246, ICBMS, Université Lyon 1, INSA-Lyon, CPE-Lyon, Bâtiment CPE, 43 bd du 11 novembre 1918, F 69622 Villeurbanne, France

^c Univ Souk Ahras, Fac. Sci. et Tech., B.P. 1553, Route de Annaba, Souk-Ahras, Algeria

^d Laboratoire de Chimie Organique appliquée, Univ Annaba, Annaba, Algeria

^e CQB-DQB Faculdade de Ciências da Universidade de Lisboa, Ed. C8, 5° Piso, Campo Grande, 1749-016 Lisbon, Portugal

^f Department of Chemistry, University of York, York, UK
E-mail: Stephen.cowling@york.ac.uk

Abstract

In this article we describe work on the synthesis of bolaphile biomimics composed of glucose head groups and steroidal units linked together by a methylene chain of varying length. The condensed phases formed by self-organization of the products as a function of temperature were characterized by differential scanning calorimetry and thermal polarized light microscopy. The results of these studies show that the thermal stabilities of the lamellar mesophases formed vary linearly as a function of increasing aliphatic composition, which reflects a linear hydrophobic–hydrophilic balance with respect to transition temperatures.

This article is part of the themed collection: In Celebration of Richard Taylor’s 65th Birthday

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DOI: https://doi.org/10.1039/C4OB02191F
Article type: Paper
Submitted: 15 Oct 2014
Accepted: 03 Nov 2014
First published: 03 Nov 2014

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Org. Biomol. Chem., 2015,13, 783-792

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Self-organizing behaviour of glycosteroidal bolaphiles: insights into lipidic microsegregation

R. Xu, F. Ali-Rachedi, N. M. Xavier, S. Chambert, F. Ferkous, Y. Queneau, S. J. Cowling, E. J. Davis and J. W. Goodby, Org. Biomol. Chem., 2015, 13, 783 DOI: 10.1039/C4OB02191F

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Organic & Biomolecular Chemistry

Self-organizing behaviour of glycosteroidal bolaphiles: insights into lipidic microsegregation†

Abstract

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Self-organizing behaviour of glycosteroidal bolaphiles: insights into lipidic microsegregation

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