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pH-Driven self-assembly of acidic microbial glycolipids

(2016) LANGMUIR. 32(25). p.6343-6359
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Abstract
Microbial glycolipids are a class of well-known compounds, but their self-assembly behavior is still not well understood. While the free carboxylic acid end group makes some of them interesting stimuli-responsive compounds, the sugar hydrophilic group and the nature of the fatty acid chain make the understanding of their self-assembly behavior in water not easy and highly unpredictable. Using cryo-transmission electron microscopy (cryo-TEM) and both pH-dependent in situ and ex situ small angle X-ray scattering (SAXS), we demonstrate that "the aqueous self-assembly at room temperature (RT) of a family of beta-D-glucose microbial glycolipids bearing a saturated and monounsaturated C18 fatty acid chain cannot be explained on the simple basis of the well-known packing parameter. Using the "pH-jump" process, we find that the molecules bearing a monosaturated fatty acid forms vesicles below pH 6.2, as expected, but the derivative with a saturated fatty acid forms infinite bilayer sheets below pH 7.8, instead of vesicles. We show that this behavior can be explained on the different bilayer membrane elasticity as a function of temperature. Membranes are either flexible or stiff for experiments performed at a temperature respectively above or below the typical melting point, T-M, of the lipidic part of each compound. Finally, we also show that the disaccharide-containing acidic cellobioselipid forms a majority of chiral fibers, instead of the expected micelles.
Keywords
UNSYMMETRICAL BOLAAMPHIPHILES, TO-VESICLE TRANSITION, RENEWABLE RESOURCES, MICELLAR STRUCTURE, SOPHOROSE LIPIDS, USTILAGO-MAYDIS, FATTY-ACIDS, MIXTURES, PK(A), BIOSURFACTANTS

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Chicago
Baccile, Niki, Mohamed Selmane, Patrick Le Griel, Sylvain Prevost, Javier Perez, Christian Stevens, Elisabeth Delbeke, et al. 2016. “pH-Driven Self-assembly of Acidic Microbial Glycolipids.” Langmuir 32 (25): 6343–6359.
APA
Baccile, N., Selmane, M., Le Griel, P., Prevost, S., Perez, J., Stevens, C., Delbeke, E., et al. (2016). pH-Driven self-assembly of acidic microbial glycolipids. LANGMUIR, 32(25), 6343–6359.
Vancouver
1.
Baccile N, Selmane M, Le Griel P, Prevost S, Perez J, Stevens C, et al. pH-Driven self-assembly of acidic microbial glycolipids. LANGMUIR. 2016;32(25):6343–59.
MLA
Baccile, Niki, Mohamed Selmane, Patrick Le Griel, et al. “pH-Driven Self-assembly of Acidic Microbial Glycolipids.” LANGMUIR 32.25 (2016): 6343–6359. Print.
@article{8057382,
  abstract     = {Microbial glycolipids are a class of well-known compounds, but their self-assembly behavior is still not well understood. While the free carboxylic acid end group makes some of them interesting stimuli-responsive compounds, the sugar hydrophilic group and the nature of the fatty acid chain make the understanding of their self-assembly behavior in water not easy and highly unpredictable. Using cryo-transmission electron microscopy (cryo-TEM) and both pH-dependent in situ and ex situ small angle X-ray scattering (SAXS), we demonstrate that {\textacutedbl}the aqueous self-assembly at room temperature (RT) of a family of beta-D-glucose microbial glycolipids bearing a saturated and monounsaturated C18 fatty acid chain cannot be explained on the simple basis of the well-known packing parameter. Using the {\textacutedbl}pH-jump{\textacutedbl} process, we find that the molecules bearing a monosaturated fatty acid forms vesicles below pH 6.2, as expected, but the derivative with a saturated fatty acid forms infinite bilayer sheets below pH 7.8, instead of vesicles. We show that this behavior can be explained on the different bilayer membrane elasticity as a function of temperature. Membranes are either flexible or stiff for experiments performed at a temperature respectively above or below the typical melting point, T-M, of the lipidic part of each compound. Finally, we also show that the disaccharide-containing acidic cellobioselipid forms a majority of chiral fibers, instead of the expected micelles.},
  author       = {Baccile, Niki and Selmane, Mohamed and Le Griel, Patrick and Prevost, Sylvain and Perez, Javier and Stevens, Christian and Delbeke, Elisabeth and Zibek, Susanne and Guenther, Michael and Soetaert, Wim and Van Bogaert, Inge and Roelants, Sophie},
  issn         = {0743-7463},
  journal      = {LANGMUIR},
  keyword      = {UNSYMMETRICAL BOLAAMPHIPHILES,TO-VESICLE TRANSITION,RENEWABLE RESOURCES,MICELLAR STRUCTURE,SOPHOROSE LIPIDS,USTILAGO-MAYDIS,FATTY-ACIDS,MIXTURES,PK(A),BIOSURFACTANTS},
  language     = {eng},
  number       = {25},
  pages        = {6343--6359},
  title        = {pH-Driven self-assembly of acidic microbial glycolipids},
  url          = {http://dx.doi.org/10.1021/acs.langmuir.6b00488},
  volume       = {32},
  year         = {2016},
}

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