130727-53-6Relevant articles and documents
Synthesis of benzaldehyde-functionalized glycans: A novel approach towards glyco-SAMs as a tool for surface plasmon resonance studies
Kopitzki, Sebastian,Jensen, Knud J.,Thiem, Joachim
experimental part, p. 7017 - 7029 (2010/09/10)
In recent years the interest in tools for investigating carbohydrateprotein (CPI) and carbohydrate-carbohydrate interactions (CCI) has increased significantly. For the investigation of CPI and CCI, several techniques employing different linking methods are available. Surface plasmon resonance (SPR) imaging is a most appropriate tool for analyzing the formation of self-assembled monolayers (SAM) of carbohydrate derivatives, which can mimic the glycocalyx. In contrast to the SPR imaging methods used previously to analyze CPI and CCI, the novel approach reported herein allows a facile and rapid synthesis of linker spacers and carbohydrate derivatives and enhances the binding event by controlling the amount and orientation of ligand. For immobilization on biorepulsive amino-functionalized SPR chips by reductive amination, diverse aldehyde-functionalized glycan structures (glucose, galactose, mannose, glucosamine, cellobiose, lactose, and lactosamine) have been synthesized in several facile steps that include olefin metathesis. Effective immobilization and the first binding studies are presented for the lectin concanavalin A.
A modular approach for the construction and modification of glyco-SAMs utilizing 1,3-dipolar cycloaddition
Kleinert, Mike,Winkler, Tobias,Terfort, Andreas,Lindhorst, Thisbe K.
scheme or table, p. 2118 - 2132 (2009/02/01)
We report the synthesis of a broad variety of functionalized molecules for assembly on gold, allowing the formation of biologically relevant SAMs by a modular approach: either utilizing 1,3-dipolar cycloaddition of alkynes and azides in solution or by 'cl
Glyco-SAMs as glycocalyx mimetics: Synthesis of L-fucose- and D-mannose-terminated building blocks
Kleinert, Mike,Roeckendorf, Niels,Lindhorst, Thisbe K.
, p. 3931 - 3940 (2007/10/03)
In the course of a project on the supramolecular functions of the glycocalyx present on eukaryotic cell surfaces, it has been our goal to prepare spacer glycosides and cluster glycosides that are suitable for the formation of self-assembled monolayers (SAMs) on gold. We have selected amino-functionalized D-mannose and L-fucose derivatives for peptide coupling to thio-functionalised alkane and alkane-oligoethylene glycol spacers such as 12 and 15. Thus, a variety of thiospacered glycosides (16-19) and cluster glycosides (23, 24, 26, 28, and 29) were synthesized, which can be assembled on gold wafers to serve as glycocalyx mimetics. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.
Gold glyconanoparticles: Synthetic polyvalent ligands mimicking glycocalyx-like surfaces as tools for glycobiological studies
Barrientos, Africa G.,De la Fuente, Jesus M.,Rojas, Teresa C.,Fernandez, Asuncion,Penades, Soledad
, p. 1909 - 1921 (2007/10/03)
A simple and versatile methodology is described for tailoring sugar-functionalised gold nanoclusters (glyconanoparticles) that have 3D polyvalent carbohydrate display and globular shapes. This methodology allows the preparation of glyconanoparticles with biologically significant oligosaccharides as well as with differing carbohydrate density. Fluorescent glyconanoparticles have been also prepared for labelling cells in biological tests. The materials are water soluble, stable under physiological conditions and present an exceptional small core size. All of them have been characterised by 1H NMR, UV and IR spectroscopy, TEM and elemental analysis. Their highly polyvalent network can mimic glycosphingolipid clustering and interactions at the plasma membrane, providing an controlled system for glycobiological studies. Furthermore, they are useful building blocks for the design of nanomaterials.
Formation of self-assembled monolayers by chemisorption of derivatives of oligo(ethylene glycol) of structure HS(CH2)11(OCH2CH2)mOH on gold
Pale-Grosdemange, Catherine,Simon, Ethan S.,Prime, Kevin L.,Whitesides, George M.
, p. 12 - 20 (2007/10/02)
This paper describes the preparation of oligo(ethylene glycol)-terminated alkanethiols having structure HS-(CH2)11(OCH2CH2)mOH (m = 3-7) and their use in the formation of self-assembled monolayers (SAMs) on gold. A combination of experimental evidence derived from X-ray photoelectron spectroscopy (XPS), measurement of contact angles, and ellipsometry implies substantial disorder in the oligo(ethylene glycol)-containing segment. The order in the -(CH2)11- group is not denned by the available evidence. The SAMs are moderately hydrophilic: θa(H2O) = 34-38°; θr(H2O) = 22-25°. A study of monolayers containing mixtures of HS(CH2)11CH3 and HS(CH2)11(OCH2CH2)6OH suggests that the oligo(ethylene glycol) moieties are effective at preventing underlying methylene groups from influencing wetting by water. A limited study demonstrates that these oligo(ethylene glycol)-containing SAMs resist the adsorption of protein from solution and suggests that SAMs will be a useful model system for studying the adsorption of proteins onto organic surfaces.
