title: Lipase catalysis and thiol-Michael addition: a relevant association for the synthesis of new surface-active carbohydrate esters.
abstract: 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.
authors.affiliation: Center for Education and Research on Macromolecules, University of Liege, Chemistry Institute, Sart-Tilman, Allée de la Chimie 3, Bat B6a, B-4000 Liege, Belgium.
authors.forename: Cédric
authors.initials: C
authors.lastname: Boyère
authors.forename: Audrey
authors.initials: A
authors.lastname: Favrelle
authors.forename: Guy
authors.initials: G
authors.lastname: Broze
authors.forename: Pascal
authors.initials: P
authors.lastname: Laurent
authors.forename: Katherine
authors.initials: K
authors.lastname: Nott
authors.forename: Michel
authors.initials: M
authors.lastname: Paquot
authors.forename: Christophe
authors.initials: C
authors.lastname: Blecker
authors.forename: Christine
authors.initials: C
authors.lastname: Jérôme
authors.forename: Antoine
authors.initials: A
authors.lastname: Debuigne
mesh_terms: D055162:Biocatalysis; D002241:Carbohydrates / Q000138:chemical synthesis* / Q000737:chemistry*; D060326:Chemistry Techniques, Synthetic; D004951:Esterification; D004952:Esters; D005656:Fungal Proteins; D008049:Lipase / Q000378:metabolism*; D008358:Mannose / Q000737:chemistry; D008689:Methacrylates / Q000737:chemistry; D013438:Sulfhydryl Compounds / Q000737:chemistry*; D013501:Surface-Active Agents / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D002241:Carbohydrates; D004952:Esters; D005656:Fungal Proteins; D008689:Methacrylates; D013438:Sulfhydryl Compounds; D013501:Surface-Active Agents; C008384:methacrylic acid; D008049:Lipase; C431349:lipase B, Candida antarctica; D008358:Mannose