thiol ene reaction; enzymatic reaction; polymer functionalization
Résumé :
[en] A novel class of surface-active carbohydrate esters is prepared by a two-step strategy that takes advantage of the selectivity of enzymatic catalysis and the versatility of the thiol-Michael addition reaction. The surfactant performance of the produced aliphatic, fluorinated and silicon based sugar esters are evaluated by surface tension measurements. The novel thiolated mannose, made available in this work, appears as a powerful building block for the incorporation of unprotected sugar moieties into complex molecules.
Centre/Unité de recherche :
Center for Education and Research on Macromolecules (CERM)
Disciplines :
Science des matériaux & ingénierie Chimie
Auteur, co-auteur :
Boyère, Cédric ; Université de Liège - ULiège > Department of Chemistry > Center for Education and Research on Macromolecules (CERM)
Favrelle, Audrey ; 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)
Laurent, Pascal ; Université de Liège - ULiège > Gembloux Agro-Bio Tech > Unit of Biological and Industrial Chemistry and Unit of General and Organic Chemistry
Nott, Katherine ; Université de Liège - ULiège > Gembloux Agro-Bio Tech > Unit of Biological and Industrial Chemistry
Paquot, Michel ; Université de Liège - ULiège > Gembloux Agro-Bio Tech > Unit of Biological and Industrial Chemistry
Blecker, Christophe ; Université de Liège - ULiège > Gembloux Agro-Bio Tech > Unit of Food Technology
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)
Langue du document :
Anglais
Titre :
Lipase catalysis and thiol-Michael addition: a relevant association for the synthesis of new surface active carbohydrate esters
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
J. Rieger, K. Van Butsele, P. Lecomte, C. Detrembleur, R. Jerome, and C. Jerome Chem. Commun. (Cambridge) 2005 274 276
J.A. Syrett, D.M. Haddleton, M.R. Whittaker, T.P. Davis, and C. Boyer Chem. Commun. (Cambridge) 47 2011 1449 1451
G. Chen, S. Amajjahe, and M.H. Stenzel Chem. Commun. (Cambridge) 2009 1198 1200
M. Semsarilar, V. Ladmiral, and S. Perrier Macromolecules 43 2010 1438 1443
S. Chang, and J. Shaw New Biotechnol. 26 2009 109 116
P. Degn, and W. Zimmermann Biotechnol. Bioeng. 74 2001 483 491
Y. Watanabe, Y. Miyawaki, S. Adachi, K. Nakanishi, and R. Matsuno Biochem. Eng. J. 8 2001 213 216
A. Favrelle, C. Boyre, P. Laurent, G. Broze, C. Blecker, M. Paquot, C. Jérôme, and A. Debuigne Carbohydr. Res. 2011 10.1016/j.carres.2011. 1004.1004
M. Takwa, K. Hult, and M. Martinelle Macromolecules 41 2008 5230 5236
C. Hedfors, K. Hult, and M. Martinelle J. Mol. Catal. B: Enzym. 66 2010 120 123
G.Z. Li, R.K. Randev, A.H. Soeriyadi, G. Rees, C. Boyer, Z. Tong, T.P. Davis, C.R. Becer, and D.M. Haddleton Polym. Chem. 1 2010 1196 1204
S. Halila, M. Manguian, S. Fort, S. Cottaz, T. Hamaide, E. Fleury, and H. Driguez Macromol. Chem. Phys. 209 2008 1282 1290
D.J. Pillion, F. Ahsan, J.J. Arnold, B.M. Balusubramanian, O. Piraner, and E. Meezan J. Pharm. Sci. 91 2002 1456 1462
G. Battaglia, R.M. La, V. Bruno, L. Arenare, R. Ippolito, A. Copani, F. Bonina, and F. Nicoletti Brain Res. 860 2000 149 156
S. Okabe, M. Suganuma, Y. Tada, Y. Ochiai, E. Sueoka, H. Kohya, A. Shibata, M. Takahashi, M. Mizutani, T. Matsuzaki, and H. Fujiki Jpn. J. Cancer Res. 90 1999 669 676
H. Maag J. Am. Oil Chem. Soc. 61 1984 259 267
T. Akimoto, K. Kawahara, Y. Nagase, and T. Aoyagi Macromol. Chem. Phys. 201 2000 2729 2734
T. Akimoto, K. Kawahara, Y. Nagase, and T. Aoyagi J. Controlled Release 77 2001 49 57
T. Akimoto, and Y. Nagase J. Controlled Release 88 2003 243 252
V. Cirkva, R. Polák, O. Paleta, K. Kefurt, J. Moravcová, M. KodIcek, and S. Forman Carbohydr. Res. 339 2004 2177 2185
I. Rico-Lattes, B. Guidetti, and A. Lattes J. Fluorine Chem. 107 2001 355 361
S. Denoyelle, A. Polidori, M. Brunelle, P.Y. Vuillaume, S. Laurent, Y. ElAzhary, and B. Pucci New J. Chem. 30 2006 629 646
M. Krafft, and J. Riess Biochimie 80 1998 489 514
S. Périno, C. Contino-Pépin, S. Jasseron, M. Rapp, J.-C. Maurizis, and B. Pucci Bioorg. Med. Chem. Lett. 16 2006 1111 1114
D.J. Holt, R.J. Payne, W.Y. Chow, and C. Abell J. Colloid Interface Sci. 350 2010 205 211
D.J. Holt, R.J. Payne, and C. Abell J. Fluorine Chem. 131 2010 398 407
M. Abla, G. Durand, and B. Pucci J. Org. Chem. 73 2008 8142 8153
J.G. Riess, and J. Greiner Carbohydr. Res. 327 2000 147 168
