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Open AccessArticle

Glycosyl-Nucleolipids as New Bioinspired Amphiphiles

by Laurent Latxague 1,2,†, Amit Patwa 1,2,†, Eric Amigues 1,2 and Philippe Barthélémy 1,2,*
1
INSERM U869, Bordeaux, F-33076, France
2
Université de Bordeaux, Bordeaux, F-33076, France
*
Author to whom correspondence should be addressed.
These authors contributed equally to this work.
Molecules 2013, 18(10), 12241-12263; https://doi.org/10.3390/molecules181012241
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)
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. View Full-Text
Keywords: nucleolipid; nucleoside; glycosyl; fluorocarbon; amphiphiles; surface tension nucleolipid; nucleoside; glycosyl; fluorocarbon; amphiphiles; surface tension
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MDPI and ACS Style

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

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