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Molecules 2013, 18(10), 12241-12263; doi:10.3390/molecules181012241
Article

Glycosyl-Nucleolipids as New Bioinspired Amphiphiles

1,2,†, 1,2,†, 1,2 and 1,2,*
1 INSERM U869, Bordeaux, F-33076, France 2 Université de Bordeaux, Bordeaux, F-33076, France These authors contributed equally to this work.
* Author to whom correspondence should be addressed.
Received: 28 August 2013 / Revised: 25 September 2013 / Accepted: 25 September 2013 / Published: 30 September 2013
(This article belongs to the Special Issue Synthesis of Nucleosides, Nucleotides and Their Derivatives)
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Abstract

Four new Glycosyl-NucleoLipid (GNL) analogs featuring either a single fluorocarbon or double hydrocarbon chains were synthesized in good yields from azido thymidine as starting material. Physicochemical studies (surface tension measurements, differential scanning calorimetry) indicate that hydroxybutanamide-based GNLs feature endothermic phase transition temperatures like the previously reported double chain glycerol-based GNLs. The second generation of GNFs featuring a free nucleobase reported here presents a better surface activity (lower glim) compared to the first generation of GNFs.
Keywords: nucleolipid; nucleoside; glycosyl; fluorocarbon; amphiphiles; surface tension nucleolipid; nucleoside; glycosyl; fluorocarbon; amphiphiles; surface tension
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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Latxague, L.; Patwa, A.; Amigues, E.; Barthélémy, P. Glycosyl-Nucleolipids as New Bioinspired Amphiphiles. Molecules 2013, 18, 12241-12263.

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