Enzymatic synthesis and surface active properties of novel hemifluorinated mannose esters

[en] The lipase-catalysed esterification of sugars with hemifluorinated acid derivatives is reported for the first time. A series of mannose modified derivatives having fluorinated chains with different length have been prepared accordingly in moderate yield. A preliminary evaluation of the surface active properties of these hemifluorinated mannose esters revealed their ability to reduce the surface tension of water much more efficiently than their aliphatic counterparts.

Research center :

Center for Education and Research on Macromolecules (CERM)

Disciplines :

Chemistry
Materials science & engineering

Author, co-author :

Favrelle, Audrey ; Université de Liège - ULiège > Department of Chemistry > Center for Education and Research on Macromolecules (CERM)

Boyère, Cédric ; 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

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 Technology

Paquot, Michel ; Université de Liège - ULiège > Gembloux Agro-Bio Tech > Unit of Biological and Industrial Chemistry

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 :

Enzymatic synthesis and surface active properties of novel hemifluorinated mannose esters

Publication date :

01 July 2011

Journal title :

Carbohydrate Research

ISSN :

0008-6215

eISSN :

1873-426X

Publisher :

Elsevier, Amsterdam, Netherlands

Volume :

346

Issue :

Pages :

1161-1164

Peer reviewed :

Peer Reviewed verified by ORBi

Additional URL :

http://www.sciencedirect.com/science?_ob=MImg&_imagekey=B6TFF-52K1T0Y-1-2&_cdi=5225&_user=532038&_pii=S0008621511001728&_origin=search&_zone=rslt_list_item&_coverDate=07%2F01%2F2011&_sk=996539990&wchp=dGLbVzz-zSkWW&md5=8d5042f9c86be57fa93d9644c4098621&ie=/sdarticle.pdf

Funders :

The French Community of Belgium in the frame of the SUPERZYM Concertated Research Actions (ARC) program
BELSPO - SPP Politique scientifique - Service Public Fédéral de Programmation Politique scientifique
F.R.S.-FNRS - Fonds de la Recherche Scientifique [BE]
Région wallonne [BE]
The TECHNOSE excellency program

Available on ORBi :

since 05 May 2011

Statistics

Number of views

75 (11 by ULiège)

Number of downloads

33 (3 by ULiège)

More statistics

Scopus citations^®

Scopus citations^®
without self-citations

OpenCitations

Bibliography

Gijsen, H. J. M.; Qiao, L.; Fitz, W.; Wong, C.-H. Chem. Rev. 1996, 96, 443-473.
Adachi, S.; Kobayashi, T. J. Biosci. Bioeng. 2005, 99, 87-94.
Watanabe, Y.; Miyawaki, Y.; Adachi, S.; Nakanishi, K.; Matsuno, R. Biochem. Eng. J. 2001, 8, 213-216.
Moreau, B.; Lognay, G. C.; Blecker, C.; Brohee, J.-C.; Chery, F.; Rollin, P.; Paquot, M.; Marlier, M. Biotechnol. Lett. 2004, 26, 419-424.
Bousquet, M.-P.; Willemot, R.-M.; Monsan, P.; Boures, E. Biotechnol. Bioeng. 1999, 63, 730-736.
Degn, P.; Pedersen, L. H.; Duus, J. O.; Zimmermann, W. Biotechnol. Lett. 1999, 21, 275-280.
Ferrer, M.; Soliveri, J.; Plou, F. J.; Lopez-Cortes, N.; Reyes-Duarte, D.; Christensen, M.; Copa-Patino, J. L.; Ballesteros, A. Enzyme Microb. Technol. 2005, 36, 391-398.
Sabeder, S.; Habulin, M.; Knez, Z. J. Food Eng. 2006, 77, 880-886.
Sabeder, S.; Habulin, M.; Knez, Z. Chem. Ind. Chem. Eng. Q. 2006, 12, 147-151.
Piccicuto, S.; Blecker, C.; Brohee, J.-C.; Mbampara, A.; Lognay, G.; Deroanne, C.; Paquot, M.; Marlier, M. Biotechnol., Agron., Soc. Environ. 2001, 5, 209-219.
Queneau, Y.; Chambert, S.; Besset, C.; Cheaib, R. Carbohydr. Res. 2008, 343, 1999-2009.
El Ghoul, M.; Escoula, B.; Rico, I.; Lattes, A. J. Fluorine Chem. 1992, 59, 107-112.
Chaudier, Y.; Barthelemy, P.; Pucci, B. Tetrahedron Lett. 2001, 42, 3583-3585.
Abouhilale, S.; Greiner, J.; Riess, J. G. J. Am. Oil Chem. Soc. 1992, 69, 1-8.
Holt, D. J.; Payne, R. J.; Chow, W. Y.; Abell, C. J. Colloid Interface Sci. 2010, 350, 205-211.
Holt, D. J.; Payne, R. J.; Abell, C. J. Fluorine Chem. 2010, 131, 398-407.
Riess, J. G.; Greiner, J. Carbohydr. Res. 2000, 327, 147-168.
Rico-Lattes, I.; Guidetti, B.; Lattes, A. J. Fluorine Chem. 2001, 107, 355-361.
Cirkva, V.; Polak, R.; Paleta, O.; Kefurt, K.; Moravcova, J.; Kodicek, M.; Forman, S. Carbohydr. Res. 2004, 339, 2177-2185.
Denoyelle, S.; Polidori, A.; Brunelle, M.; Vuillaume, P. Y.; Laurent, S.; ElAzhary, Y.; Pucci, B. New J. Chem. 2006, 30, 629-646.
Perino, S.; Contino-Pepin, C.; Jasseron, S.; Rapp, M.; Maurizis, J.-C.; Pucci, B. Bioorg. Med. Chem. Lett. 2006, 16, 1111-1114.
Brunelle, M.; Polidori, A.; Denoyelle, S.; Fabiano, A.-S.; Vuillaume, P. Y.; Laurent-Lewandowski, S.; Pucci, B. C.R. Chim. 2009, 12, 188-208.
Mesiano, A. J.; Beckman, E. J.; Russell, A. J. Biotechnol. Prog. 2000, 16, 64-68.
Polidori, A.; Presset, M.; Lebaupain, F.; Ameduri, B.; Popot, J.-L.; Breyton, C.; Pucci, B. Bioorg. Med. Chem. Lett. 2006, 16, 5827-5831.
Abla, M.; Durand, G.; Pucci, B. J. Org. Chem. 2008, 73, 8142-8153.
Jiang, H.-L.; Kang, M. L.; Quan, J.-S.; Kang, S. G.; Akaike, T.; Yoo, H. S.; Cho, C.-S. Biomaterials 2008, 29, 1931-1939.
Zhou, X.; Liu, B.; Yu, X.; Zha, X.; Zhang, X.; Wang, X.; Chen, Y.; Chen, Y.; Chen, Y.; Shan, Y.; Jin, Y.; Wu, Y.; Liu, J.; Kong, W.; Shen, J. Biomaterials 2007, 28, 4684-4692.
Goss, K.-U. Environ. Sci. Technol. 2008, 42, 5032.
Hollmann, F.; Grzebyk, P.; Heinrichs, V.; Doderer, K.; Thum, O. J. Mol. Catal. B: Enzym. 2009, 57, 257-261.
Garofalakis, G.; Murray, B. S.; Sarney, D. B. J. Colloid Interface Sci. 2000, 229, 391-398.