Synthesis of unsymmetrical saturated or diacetylenic cationic bolaamphiphiles

Mathieu Berchel; Loïc Lemiègre; Sylvain Trépout; Olivier Lambert; Jelena Jeftić; Thierry Benvegnu

doi:10.1016/j.tetlet.2008.10.073

Synthesis of unsymmetrical saturated or diacetylenic cationic bolaamphiphiles

Mathieu Berchel, Loïc Lemiègre, Sylvain Trépout, Olivier Lambert, Jelena Jeftić, Thierry Benvegnu

Research output: Contribution to journal › Article › Research › peer-review

17 Citations (Scopus)

Abstract

This work presents the synthesis of novel unsymmetrical bolaamphiphiles bearing a sugar residue and a cationic glycine betaine moiety connected to both ends of a C₂₂ or C₃₂ oligomethylene bridging chain possessing or not a diacetylenic unit. Preliminary transmission electron microscopy (TEM) studies revealed the polymorphism of these bola lipids with regard to their self-assembled morphologies in water depending on the presence or not of the diacetylenic functionality and on alkyl chain length.

Original language	English
Pages (from-to)	7419-7422
Number of pages	4
Journal	Tetrahedron Letters
Volume	49
Issue number	52
DOIs	https://doi.org/10.1016/j.tetlet.2008.10.073
Publication status	Published - 22 Dec 2008
Externally published	Yes

Keywords

Bolaamphiphile
Hydrogel
Supramolecular assemblies
Synthesis
Transmission electron microscopy
Tubules
Vesicles

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10.1016/j.tetlet.2008.10.073

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title = "Synthesis of unsymmetrical saturated or diacetylenic cationic bolaamphiphiles",

abstract = "This work presents the synthesis of novel unsymmetrical bolaamphiphiles bearing a sugar residue and a cationic glycine betaine moiety connected to both ends of a C22 or C32 oligomethylene bridging chain possessing or not a diacetylenic unit. Preliminary transmission electron microscopy (TEM) studies revealed the polymorphism of these bola lipids with regard to their self-assembled morphologies in water depending on the presence or not of the diacetylenic functionality and on alkyl chain length.",

keywords = "Bolaamphiphile, Hydrogel, Supramolecular assemblies, Synthesis, Transmission electron microscopy, Tubules, Vesicles",

author = "Mathieu Berchel and Lo{\"i}c Lemi{\`e}gre and Sylvain Tr{\'e}pout and Olivier Lambert and Jelena Jefti{\'c} and Thierry Benvegnu",

note = "Funding Information: M.B. is grateful to the Minist{\`e}re de l{\textquoteright}Education Nationale et de la Recherche (France) for a PhD grant. J.-M. Verbavatz is acknowledged for his work in FFEM studies. ",

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T1 - Synthesis of unsymmetrical saturated or diacetylenic cationic bolaamphiphiles

AU - Berchel, Mathieu

AU - Lemiègre, Loïc

AU - Trépout, Sylvain

AU - Lambert, Olivier

AU - Jeftić, Jelena

AU - Benvegnu, Thierry

N1 - Funding Information: M.B. is grateful to the Ministère de l’Education Nationale et de la Recherche (France) for a PhD grant. J.-M. Verbavatz is acknowledged for his work in FFEM studies.

PY - 2008/12/22

Y1 - 2008/12/22

N2 - This work presents the synthesis of novel unsymmetrical bolaamphiphiles bearing a sugar residue and a cationic glycine betaine moiety connected to both ends of a C22 or C32 oligomethylene bridging chain possessing or not a diacetylenic unit. Preliminary transmission electron microscopy (TEM) studies revealed the polymorphism of these bola lipids with regard to their self-assembled morphologies in water depending on the presence or not of the diacetylenic functionality and on alkyl chain length.

AB - This work presents the synthesis of novel unsymmetrical bolaamphiphiles bearing a sugar residue and a cationic glycine betaine moiety connected to both ends of a C22 or C32 oligomethylene bridging chain possessing or not a diacetylenic unit. Preliminary transmission electron microscopy (TEM) studies revealed the polymorphism of these bola lipids with regard to their self-assembled morphologies in water depending on the presence or not of the diacetylenic functionality and on alkyl chain length.

KW - Bolaamphiphile

KW - Hydrogel

KW - Supramolecular assemblies

KW - Synthesis

KW - Transmission electron microscopy

KW - Tubules

KW - Vesicles

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DO - 10.1016/j.tetlet.2008.10.073

M3 - Article

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SN - 0040-4039

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SP - 7419

EP - 7422

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 52

ER -

Synthesis of unsymmetrical saturated or diacetylenic cationic bolaamphiphiles

Abstract

Keywords

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