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Synthesis and self-assembly of aminyl and alkynyl substituted sophorolipids

Abdoul Aziz Ba, Jonas Everaert (UGent) , Alexandre Poirier, Patrick Le Griel, Wim Soetaert (UGent) , Sophie Roelants (UGent) , Daniel Hermida-Merino, Christian Stevens (UGent) and Niki Baccile
(2020) GREEN CHEMISTRY. 22(23). p.8323-8336
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Abstract
Sophorolipids are one of the most important microbial biosurfactants, because of their large-scale production and applications developed so far in the fields of detergency, microbiology, cosmetics or environmental science. However, the structural variety of native sophorolipids is limited/restricted, a limiting fact for the development of new properties and their potential applications. In their open acidic form, C18:1 sophorolipids (SL) are classically composed of a sophorose headgroup and a carboxylic acid (COOH) end-group. The carboxyl group gives them unique pH-responsive properties, but it is a poorly reactive group and its charge can only be negative. To develop a new generation of pH-responsive, positively charged, SL and to improve their reactivity for further functionalization, we develop here SL with an amine (-NH2) or terminal alkyne (-CCH) end-group analogues. The amine group generates positively charged SL and is more reactive than carboxylic acids, e.g. towards aldehydes; the alkyne group provides access to copper-based click chemistry. In this work, we synthesized (C18:1) and (C18:0) -NH2 and (C18:1) -CCH sophorolipid derivatives and we study their self-assembly properties in response to pH and/or temperature changes by means of static and dynamic light scattering, small angle (X-ray, neutron) scattering and cryogenic electron microscopy. Monounsaturated aminyl SL-C18:1-NH2 sophorolipids form a micellar phase in their neutral form at high pH and a mixed micellar-bilayer phase in their positively charged form at low pH. Saturated aminyl SL-C18:0-NH2 sophorolipids form a micellar phase in their charged form at low pH and a twisted ribbon phase in their neutral form at high pH and monounsaturated alkynyl SL-C18:1-CCH sophorolipids form a main micellar phase at T > 51.8 degrees C and a twisted ribbon phase at T < 51.8 degrees C.
Keywords
Pollution, Environmental Chemistry, GLYCOLIPID BIOSURFACTANTS, POTENTIAL APPLICATIONS, INTERFACIAL PROPERTIES, MICROBIAL-PRODUCTION, LAMELLAR HYDROGELS, CANDIDA-BOMBICOLA, PH, SURFACTANT, MICELLES, ORGANIZATION

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MLA
Ba, Abdoul Aziz, et al. “Synthesis and Self-Assembly of Aminyl and Alkynyl Substituted Sophorolipids.” GREEN CHEMISTRY, vol. 22, no. 23, 2020, pp. 8323–36, doi:10.1039/d0gc03053h.
APA
Ba, A. A., Everaert, J., Poirier, A., Le Griel, P., Soetaert, W., Roelants, S., … Baccile, N. (2020). Synthesis and self-assembly of aminyl and alkynyl substituted sophorolipids. GREEN CHEMISTRY, 22(23), 8323–8336. https://doi.org/10.1039/d0gc03053h
Chicago author-date
Ba, Abdoul Aziz, Jonas Everaert, Alexandre Poirier, Patrick Le Griel, Wim Soetaert, Sophie Roelants, Daniel Hermida-Merino, Christian Stevens, and Niki Baccile. 2020. “Synthesis and Self-Assembly of Aminyl and Alkynyl Substituted Sophorolipids.” GREEN CHEMISTRY 22 (23): 8323–36. https://doi.org/10.1039/d0gc03053h.
Chicago author-date (all authors)
Ba, Abdoul Aziz, Jonas Everaert, Alexandre Poirier, Patrick Le Griel, Wim Soetaert, Sophie Roelants, Daniel Hermida-Merino, Christian Stevens, and Niki Baccile. 2020. “Synthesis and Self-Assembly of Aminyl and Alkynyl Substituted Sophorolipids.” GREEN CHEMISTRY 22 (23): 8323–8336. doi:10.1039/d0gc03053h.
Vancouver
1.
Ba AA, Everaert J, Poirier A, Le Griel P, Soetaert W, Roelants S, et al. Synthesis and self-assembly of aminyl and alkynyl substituted sophorolipids. GREEN CHEMISTRY. 2020;22(23):8323–36.
IEEE
[1]
A. A. Ba et al., “Synthesis and self-assembly of aminyl and alkynyl substituted sophorolipids,” GREEN CHEMISTRY, vol. 22, no. 23, pp. 8323–8336, 2020.
@article{8680852,
  abstract     = {{Sophorolipids are one of the most important microbial biosurfactants, because of their large-scale production and applications developed so far in the fields of detergency, microbiology, cosmetics or environmental science. However, the structural variety of native sophorolipids is limited/restricted, a limiting fact for the development of new properties and their potential applications. In their open acidic form, C18:1 sophorolipids (SL) are classically composed of a sophorose headgroup and a carboxylic acid (COOH) end-group. The carboxyl group gives them unique pH-responsive properties, but it is a poorly reactive group and its charge can only be negative. To develop a new generation of pH-responsive, positively charged, SL and to improve their reactivity for further functionalization, we develop here SL with an amine (-NH2) or terminal alkyne (-CCH) end-group analogues. The amine group generates positively charged SL and is more reactive than carboxylic acids, e.g. towards aldehydes; the alkyne group provides access to copper-based click chemistry. In this work, we synthesized (C18:1) and (C18:0) -NH2 and (C18:1) -CCH sophorolipid derivatives and we study their self-assembly properties in response to pH and/or temperature changes by means of static and dynamic light scattering, small angle (X-ray, neutron) scattering and cryogenic electron microscopy. Monounsaturated aminyl SL-C18:1-NH2 sophorolipids form a micellar phase in their neutral form at high pH and a mixed micellar-bilayer phase in their positively charged form at low pH. Saturated aminyl SL-C18:0-NH2 sophorolipids form a micellar phase in their charged form at low pH and a twisted ribbon phase in their neutral form at high pH and monounsaturated alkynyl SL-C18:1-CCH sophorolipids form a main micellar phase at T > 51.8 degrees C and a twisted ribbon phase at T < 51.8 degrees C.}},
  author       = {{Ba, Abdoul Aziz and Everaert, Jonas and Poirier, Alexandre and Le Griel, Patrick and Soetaert, Wim and Roelants, Sophie and Hermida-Merino, Daniel and Stevens, Christian and Baccile, Niki}},
  issn         = {{1463-9262}},
  journal      = {{GREEN CHEMISTRY}},
  keywords     = {{Pollution,Environmental Chemistry,GLYCOLIPID BIOSURFACTANTS,POTENTIAL APPLICATIONS,INTERFACIAL PROPERTIES,MICROBIAL-PRODUCTION,LAMELLAR HYDROGELS,CANDIDA-BOMBICOLA,PH,SURFACTANT,MICELLES,ORGANIZATION}},
  language     = {{eng}},
  number       = {{23}},
  pages        = {{8323--8336}},
  title        = {{Synthesis and self-assembly of aminyl and alkynyl substituted sophorolipids}},
  url          = {{http://doi.org/10.1039/d0gc03053h}},
  volume       = {{22}},
  year         = {{2020}},
}
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