@misc{10481/87223,
year = {2012},
month = {3},
url = {https://hdl.handle.net/10481/87223},
abstract = {Carbohydrate-mediated molecular recognition is
involved in many biological aspects such as cellular adhesion,
immune response, blood coagulation, inflammation, and infection.
Considering the crucial importance of such biological events in
which proteins are normally involved, synthetic saccharide-based
systems have emerged as powerful tools for the understanding of
protein−carbohydrate interactions. As a new approach to create
saccharide-based systems, a set of representative monosaccharides
(D-mannose, D-glucose, N-acetyl-D-glucosamine, and L-fucose) and
disaccharides (lactose, maltose, and melibiose) were derivatized at
their anomeric carbon with a vinyl sulfone group spanned by an
ethylthio linker. This vinyl sulfone functionalization is demonstrated
to be a general strategy for the covalent linkage of a saccharide in
mild conditions via Michael-type additions with the amine and thiol
groups from functionalized supports and those naturally present in biomolecules. The introduction of the ethylthio linker
between the biorecognizable element (i.e., saccharide) and the reactive group (i.e., vinyl sulfone) was found to preserve the
functionality of the former. The capability of the vinyl sulfone saccharides for the study of lectin−carbohydrate interactions was
demonstrated by (i) immobilizing them on both amine-functionalized supports (glass slides and microwell plates) and
polylysine-coated glass slides to create sugar arrays that selectively bind lectins (ii) coupling to model proteins to yield
neoglycoproteins that are recognized by lectins and (iii) using vinyl sulfone saccharides as tags to allow the detection of the
labeled biomolecule by HRP-lectins. The above results were further put tothe test with a real case: detection of carbohydrate
binding proteins present in rice (Oryza sativa)},
organization = {Dirección General de Investigación Científica y Técnica (DGICYT) (CTQ2008-01754)},
organization = {Junta de Andalucía (P07-FQM-02899)},
organization = {University of Granada},
publisher = {ACS},
keywords = {Vinyl sulfone},
keywords = {Lectins},
keywords = {Carbohydrates},
title = {Vinyl Sulfone Functionalization: A Feasible Approach for the Study of the Lectin−Carbohydrate Interactions},
doi = {10.1021/bc200681c},
author = {López Jaramillo, Francisco Javier and Ortega-Muñoz, Mariano and Megía Fernández, Alicia and Hernández Mateo, Fernando and Santoyo González, Francisco},
}