Vinyl Sulfone Functionalization: A Feasible Approach for the Study of the Lectin鈥揅arbohydrate Interactions

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• 作者：Francisco Javier Lopez-Jaramillo ; Mariano Ortega-Mu帽oz ; Alicia Megia-Fernandez ; Fernando Hernandez-Mateo ; Francisco Santoyo-Gonzalez
• 刊名：Bioconjugate Chemistry
• 出版年：2012
• 出版时间：April 18, 2012
• 年：2012
• 卷：23
• 期：4
• 页码：846-855
• 全文大小：342K
• 年卷期：v.23,no.4(April 18, 2012)
• ISSN：1520-4812

文摘

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鈥揷arbohydrate 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鈥揷arbohydrate 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).