Synthesis and physico-chemical characterization of bolaamphiphiles derived from alkenyl d-xylosides

作者: Magali Deleu , Céline Damez , Sylvain Gatard , Katherine Nott , Michel Paquot

DOI: 10.1039/C1NJ20158A

关键词:

摘要: The two step synthesis of a new series bolaamphiphiles derived from alkenyl D-xylosides is described. Yields between 57 and 90% have been reached. Aggregation behavior membrane interaction properties particular sugar-bolaform composed xylose heads connected by an ether link to hydrophobic chain comprising 18 carbon atoms insaturation were studied. Its CAC value (∼0.05 mM) low compared those conventional surfactants. Thermodynamic analysis has revealed that the aggregation phenomenon mainly driven entropy process. compound able interact with DPPC monolayers, in if their surface pressure ≥15 mN m−1. Our results highlight potential this bolaamphiphile as surfactant interacting agent.

参考文章(63)
Magali Deleu, Michel Paquot, Tommy Nylander, Effect of Fengycin, a Lipopeptide Produced by Bacillus subtilis, on Model Biomembranes Biophysical Journal. ,vol. 94, pp. 2667- 2679 ,(2008) , 10.1529/BIOPHYSJ.107.114090
Rachel Auzély-Velty, Thierry Benvegnu, Grahame Mackenzie, Julie A Haley, John W Goodby, Daniel Plusquellec, Synthesis and liquid-crystalline properties of novel archaeal diether-type glycolipids possessing one or two furanosyl units Carbohydrate Research. ,vol. 314, pp. 65- 77 ,(1998) , 10.1016/S0008-6215(98)00291-2
Boris Estrine, Sandrine Bouquillon, Françoise Hénin, Jacques Muzart, Recycling in telomerization of butadiene withD-xylose: Pd(TPPTS)n-KF/Al2O3 as an active catalyst Applied Organometallic Chemistry. ,vol. 21, pp. 945- 946 ,(2007) , 10.1002/AOC.1316
Thierry Benvegnu, Mickaëlle Brard, Daniel Plusquellec, Archaeabacteria bipolar lipid analogues: structure, synthesis and lyotropic properties Current Opinion in Colloid & Interface Science. ,vol. 8, pp. 469- 479 ,(2004) , 10.1016/J.COCIS.2004.01.005
Pierandrea Lo Nostro, Giuseppe Briganti, Sow-Hsin Chen, Structural properties of vesicles produced from a new bipolar lipid Journal of Colloid and Interface Science. ,vol. 142, pp. 214- 223 ,(1991) , 10.1016/0021-9797(91)90048-D
Derek Marsh, Lateral pressure in membranes Biochimica et Biophysica Acta. ,vol. 1286, pp. 183- 223 ,(1996) , 10.1016/S0304-4157(96)00009-3
Céline Satgé, Robert Granet, Bernard Verneuil, Yves Champavier, Pierre Krausz, Synthesis and properties of new bolaform and macrocyclic galactose-based surfactants obtained by olefin metathesis. Carbohydrate Research. ,vol. 339, pp. 1243- 1254 ,(2004) , 10.1016/J.CARRES.2004.03.003
Kiyoshi Yoshida, Shigekazu Nakajima, Takeshi Wakamatsu, Yoshio Ban, Masakatsu Shibasaki, A general procedure for the catalytic hydrogenolysis of N-benzylamines under extremely mild conditions Heterocycles. ,vol. 27, pp. 1167- 1168 ,(1988) , 10.3987/COM-88-4525
Isabelle Rico-Lattes, Armand Lattes, Synthesis of new sugar-based surfactants having biological applications: key role of their self-association Colloids and Surfaces A: Physicochemical and Engineering Aspects. ,vol. 123-124, pp. 37- 48 ,(1997) , 10.1016/S0927-7757(96)03778-8