[en] An original and versatile method for the synthesis of a range of novel mannose-based surfactants was developed via metal-free photo-induced thiol-ene/-yne “click” reactions. This light-mediated hydrothiolation reaction involving a thiolated mannose was successfully applied to terminal and internal alkenes, dienes and alkynes, leading to monocatenary, branched, double-headed and bolaform amphiphilic carbohydrate esters,respectively. A surface activity study showed that these new compounds possess valuable properties and display specific behavior at the air-water interface. It also demonstrated the greater flexibility of the thioether moiety in the spacer of the surfactants produced via a thiol-ene reaction in comparison withthe triazole heterocyclic rings in similar glucose-based surfactants synthesized elsewhere by the alkyne-azide 1,3-dipolar addition.
Research center :
Center for Education and Research on Macromolecules (CERM)
Disciplines :
Chemistry Materials science & engineering
Author, co-author :
Boyère, Cédric ; Université de Liège - ULiège > Department of Chemistry > Center for Education and Research on Macromolecules (CERM)
Broze, Guy ; Université de Liège - ULiège > Department of Chemistry > Center for Education and Research on Macromolecules (CERM)
Blecker, Christophe ; Université de Liège - ULiège > Gembloux Agro-Bio Tech > Unit of Food Science and Formulation
Jérôme, Christine ; Université de Liège - ULiège > Department of Chemistry > Center for Education and Research on Macromolecules (CERM)
Debuigne, Antoine ; Université de Liège - ULiège > Department of Chemistry > Center for Education and Research on Macromolecules (CERM)
Language :
English
Title :
Monocatenary, branched, double-headed and bolaform surface active carbohydrate esters via photochemical thiol-ene/-yne reactions
The French Community of Belgium in the frame of the SUPERZYM-ARC program BELSPO - SPP Politique scientifique - Service Public Fédéral de Programmation Politique scientifique F.R.S.-FNRS - Fonds de la Recherche Scientifique [BE]
C.C. Ruiz Sugar-based Surfactants; Fundamentals and Applications 2009 CRC Press
Y. Queneau, S. Chambert, C. Besset, and R. Cheaib Carbohydr. Res. 343 2008 1999 2009
R. Hashim, H.H.A. Hashim, N.Z.M. Rodzi, R.S.D. Hussen, and T. Heidelberg Thin Solid Films 509 2006 27 35
H.M. von Minden, M. Morr, G. Milkereit, E. Heinz, and V. Vill Chem. Phys. Lipids 114 2002 55 80
N. Ahmad, R. Ramsch, J. Esquena, C. Solans, H.A. Tajuddin, and R. Hashim Langmuir 28 2011 2395 2403
B. Schuur, A. Wagenaar, A. Heeres, and E.H.J. Heeres Carbohydr. Res. 339 2004 1147 1153
M. Deleu, C. Damez, S. Gatard, K. Nott, M. Paquot, and S. Bouquillon New J. Chem. 35 2011 2258 2266
A. Wagenaar, and J.B.F.N. Engberts Tetrahedron 63 2007 10622 10629
C. Satgé, R. Granet, B. Verneuil, Y. Champavier, and P. Krausz Carbohydr. Res. 339 2004 1243 1254
V. Neto, R. Granet, and P. Krausz Tetrahedron 66 2010 4633 4646
N. Jayaraman, M. Kumar Singh, D.S. Shankar Rao, and S.K. Prasad J. Mater. Chem. 17 2007 2228 2232
G. Milkereit, V.M. Garamus, K. Veermans, R. Willumeit, and V. Vill Chem. Phys. Lipids 131 2004 51 61
Razafindralambo, H.; Blecker, C.; Paquot, M. In Advanced in Chemical Engineering, Nawaz, Z., Naveed S., Eds.; InTech, 2012; Chapter 8, pp 215-228.
J.W. Goodby, V. Gortz, S.J. Cowling, G. Mackenzie, P. Martin, D. Plusquellec, T. Benvegnu, P. Boullanger, D. Lafont, Y. Queneau, S. Chambert, and J. Fitremann Chem. Soc. Rev. 36 2007 1971 2032
V. Vill, and R. Hashim Curr. Opin. Colloid Interface Sci. 7 2002 395 409
I. Rico-Lattes, and A. Lattes Colloids Surf., A 123-124 1997 37 48
I. Rico-Lattes, M.F. Gouzy, C. Andre-Barres, B. Guidetti, and A. Lattes Biochimie 80 1998 483 487
L. Chaveriat, I. Gosselin, C. Machut, and P. Martin Eur. J. Med. Chem. 62 2013 177 186
