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Ulf J. Nilsson - One of the best experts on this subject based on the ideXlab platform.
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didecyl squarate a practical amino reactive cross linking Reagent for neoglycoconjugate synthesis
Glycoconjugate Journal, 2001Co-Authors: Anders Bergh, Bengtgoran Magnusson, Ulf Wellmar, Jörgen Ohlsson, Ulf J. NilssonAbstract:The present paper describes the synthesis and use of the hydrophobic squaric decyl ester glycosides in neoglycoconjugate chemistry. The 2-aminoethyl glycosides of α-D-mannopyranose, lactose, globotriose, globotetraose, GM3, and sialyl Lewisx, as well as the 2-(2-aminoethylthio)ethyl glycoside of α-D-mannopyranose, β-D-glucopyranose, and galabiose were reacted with squaric acid didecyl ester to afford the hydrophobic squaric decyl ester glycosides. These glycosides were efficient Reagents for the conjugation to amino-functional microtiter plates, BSA and aminated Sepharose EAH 4B. The decyl ester moiety of the squaric decyl ester glycosides constitutes a traceless hydrophobic tag, which has the major advantage, as compared to the corresponding ethyl esters, that it enables easy purification of the glycosides with silica chromatography and that unreacted excesses glycosides from conjugation reaction mixtures can easily be recovered by means of C18 solid phase extraction.
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Didecyl squarate—A practical amino-reactive Cross-Linking Reagent for neoglycoconjugate synthesis
Glycoconjugate Journal, 2001Co-Authors: Anders Bergh, Bengtgoran Magnusson, Ulf Wellmar, Jörgen Ohlsson, Ulf J. NilssonAbstract:The present paper describes the synthesis and use of the hydrophobic squaric decyl ester glycosides in neoglycoconjugate chemistry. The 2-aminoethyl glycosides of α-D-mannopyranose, lactose, globotriose, globotetraose, GM3, and sialyl Lewis^x, as well as the 2-(2-aminoethylthio)ethyl glycoside of α-D-mannopyranose, β-D-glucopyranose, and galabiose were reacted with squaric acid didecyl ester to afford the hydrophobic squaric decyl ester glycosides. These glycosides were efficient Reagents for the conjugation to amino-functional microtiter plates, BSA and aminated Sepharose EAH 4B. The decyl ester moiety of the squaric decyl ester glycosides constitutes a traceless hydrophobic tag, which has the major advantage, as compared to the corresponding ethyl esters, that it enables easy purification of the glycosides with silica chromatography and that unreacted excesses glycosides from conjugation reaction mixtures can easily be recovered by means of C18 solid phase extraction.
Ramachandra S. Hosmane - One of the best experts on this subject based on the ideXlab platform.
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a novel cross linking Reagent for biomacromolecular modification bis phenoxycarbonylethyl phosphinic acid
Bioorganic & Medicinal Chemistry Letters, 1996Co-Authors: Vishweshwar S Bhadti, Prasad S Peri, Ramachandra S. HosmaneAbstract:Abstract Synthesis, properties, and reactions of the title Reagent, bis(phenoxycarbonylethyl)phosphinic acid, are reported. The Reagent's utility for biomacromolecular modification has been demonstrated by successfully Cross-Linking human hemoglobin.
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the synthesis of a potential cross linking Reagent 2 2 sulfonylbis 3 benzylamino e e n 2 oxoethyl propenamide
Tetrahedron Letters, 1992Co-Authors: Craig M Bertha, Ramachandra S. HosmaneAbstract:Abstract The synthesis of the title bis-aldehydic Reagent (3) with potential applications in biomacromolecular Cross-Linking is reported.
Pierre-yves Renard - One of the best experts on this subject based on the ideXlab platform.
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The first "ready-to-use" benzene-based heterotrifunctional cross-linker for multiple bioconjugation.
Organic and Biomolecular Chemistry, 2013Co-Authors: Guillaume Viault, Nicolas Maindron, Pierre-yves Renard, Sébastien Dautrey, Julie Hardouin, Anthony RomieuAbstract:The synthesis and applications of the first water-soluble benzene derivative bearing a set of three different and orthogonal bioconjugatable groups (aminooxy, azido and thiol) are described. The combined use of a 5-amino isophthalic acid scaffold and unusual acid-labile protecting groups for temporarily masking aminooxy and thiol moieties has enabled the development of a highly convergent approach towards the synthesis of such a trivalent bioconjugation platform in good yields. The potential utility of this "ready-to-use" Cross-Linking Reagent for creating complex and fragile tri-component (bio)molecular systems was illustrated through (1) the rapid preparation of a three-colour FRET cascade with valuable spectral properties and (2) the luminescent/fluorescent labelling of peptides and peptide-oligonucleotide conjugates. Thus, such (bio)molecular assemblies were readily obtained via a three-step process or in a "one-pot" manner, both involving oxime ligation, thiol-alkylation (S(N)2 or Michael addition) and copper-catalysed azide-alkyne 1,3-dipolar cycloaddition (CuAAC) reactions.
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A universal and ready-to-use heterotrifunctional Cross-Linking Reagent for facile synthetic access to sophisticated bioconjugates.
Organic and Biomolecular Chemistry, 2010Co-Authors: Guillaume Clave, Mélanie Flaender, Hervé Volland, Didier Gasparutto, Anthony Romieu, Pierre-yves RenardAbstract:We describe for the first time, the synthesis and some bioconjugation applications of an original heterotrifunctional Cross-Linking Reagent (also named tripod) bearing three different bioorthogonal functional groups which are fully compatible amongst themselves. Contrary to the first generation tripod recently reported by us (Org. Biomol. Chem., 2008, 6, 3065), the use of an azido group instead of the nucleophile-sensitive active carbamate moiety enables us to reach the targeted chemical orthogonality without the use of temporary aminooxy- and thiol protecting groups. Thus, the preparation of sophisticated bioconjugates through the sequential derivatisation of the tripod by means of copper-mediated 1,3-dipolar cycloaddition, oxime ligation and aqueous compatible mild thiol-alkylation reactions, is significantly simpler and more convenient. The chemoselective bioconjugation protocols were optimised through the preparation of FRET cassettes based on cyanine and/or xanthene fluorescent dye pairs and subsequent anchoring to fragile biomolecules. The applicability of this universal Cross-Linking Reagent was also illustrated by the preparation of biochips suitable for aflatoxin B1 detection through the SPIT-FRI method.
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a novel heterotrifunctional peptide based cross linking Reagent for facile access to bioconjugates applications to peptide fluorescent labelling and immobilisation
Organic and Biomolecular Chemistry, 2008Co-Authors: Antoine Hoang, Francois Perraut, H. Boutal, Hervé Volland, Pierre-yves Renard, Guillaume Clave, Anthony RomieuAbstract:A convenient, versatile and straightforward synthesis of a novel heterotrifunctional peptide-based linker molecule is described. This generic bio-labelling Reagent contains an amine-reactive N-hydroxysuccinimidyl carbamate moiety, an aldehyde/ketone-reactive aminooxy group and a thiol group with a propensity to form urea, oxime and thioether linkages respectively. The full chemical orthogonality between the free aminooxy and thiol functionalities was demonstrated through the preparation of a fluorescent Reagent suitable for the selective staining of a carboxaldehyde-modified surface by means of oxime ligation. The absence of reactivity of these two functions toward the nucleophile-sensitive active carbamate was obtained by using temporary aminooxy- and thiol-protecting groups removable under mild conditions. The utility of the linker molecule to cross-link three different molecular partners has been illustrated by the preparation of fluorescent tripod-functionalised surfaces which may be useful in developing new peptide microarrays and related immunosensors.
Anthony Romieu - One of the best experts on this subject based on the ideXlab platform.
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The first "ready-to-use" benzene-based heterotrifunctional cross-linker for multiple bioconjugation.
Organic and Biomolecular Chemistry, 2013Co-Authors: Guillaume Viault, Nicolas Maindron, Pierre-yves Renard, Sébastien Dautrey, Julie Hardouin, Anthony RomieuAbstract:The synthesis and applications of the first water-soluble benzene derivative bearing a set of three different and orthogonal bioconjugatable groups (aminooxy, azido and thiol) are described. The combined use of a 5-amino isophthalic acid scaffold and unusual acid-labile protecting groups for temporarily masking aminooxy and thiol moieties has enabled the development of a highly convergent approach towards the synthesis of such a trivalent bioconjugation platform in good yields. The potential utility of this "ready-to-use" Cross-Linking Reagent for creating complex and fragile tri-component (bio)molecular systems was illustrated through (1) the rapid preparation of a three-colour FRET cascade with valuable spectral properties and (2) the luminescent/fluorescent labelling of peptides and peptide-oligonucleotide conjugates. Thus, such (bio)molecular assemblies were readily obtained via a three-step process or in a "one-pot" manner, both involving oxime ligation, thiol-alkylation (S(N)2 or Michael addition) and copper-catalysed azide-alkyne 1,3-dipolar cycloaddition (CuAAC) reactions.
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A universal and ready-to-use heterotrifunctional Cross-Linking Reagent for facile synthetic access to sophisticated bioconjugates.
Organic and Biomolecular Chemistry, 2010Co-Authors: Guillaume Clave, Mélanie Flaender, Hervé Volland, Didier Gasparutto, Anthony Romieu, Pierre-yves RenardAbstract:We describe for the first time, the synthesis and some bioconjugation applications of an original heterotrifunctional Cross-Linking Reagent (also named tripod) bearing three different bioorthogonal functional groups which are fully compatible amongst themselves. Contrary to the first generation tripod recently reported by us (Org. Biomol. Chem., 2008, 6, 3065), the use of an azido group instead of the nucleophile-sensitive active carbamate moiety enables us to reach the targeted chemical orthogonality without the use of temporary aminooxy- and thiol protecting groups. Thus, the preparation of sophisticated bioconjugates through the sequential derivatisation of the tripod by means of copper-mediated 1,3-dipolar cycloaddition, oxime ligation and aqueous compatible mild thiol-alkylation reactions, is significantly simpler and more convenient. The chemoselective bioconjugation protocols were optimised through the preparation of FRET cassettes based on cyanine and/or xanthene fluorescent dye pairs and subsequent anchoring to fragile biomolecules. The applicability of this universal Cross-Linking Reagent was also illustrated by the preparation of biochips suitable for aflatoxin B1 detection through the SPIT-FRI method.
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a novel heterotrifunctional peptide based cross linking Reagent for facile access to bioconjugates applications to peptide fluorescent labelling and immobilisation
Organic and Biomolecular Chemistry, 2008Co-Authors: Antoine Hoang, Francois Perraut, H. Boutal, Hervé Volland, Pierre-yves Renard, Guillaume Clave, Anthony RomieuAbstract:A convenient, versatile and straightforward synthesis of a novel heterotrifunctional peptide-based linker molecule is described. This generic bio-labelling Reagent contains an amine-reactive N-hydroxysuccinimidyl carbamate moiety, an aldehyde/ketone-reactive aminooxy group and a thiol group with a propensity to form urea, oxime and thioether linkages respectively. The full chemical orthogonality between the free aminooxy and thiol functionalities was demonstrated through the preparation of a fluorescent Reagent suitable for the selective staining of a carboxaldehyde-modified surface by means of oxime ligation. The absence of reactivity of these two functions toward the nucleophile-sensitive active carbamate was obtained by using temporary aminooxy- and thiol-protecting groups removable under mild conditions. The utility of the linker molecule to cross-link three different molecular partners has been illustrated by the preparation of fluorescent tripod-functionalised surfaces which may be useful in developing new peptide microarrays and related immunosensors.
Anders Bergh - One of the best experts on this subject based on the ideXlab platform.
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didecyl squarate a practical amino reactive cross linking Reagent for neoglycoconjugate synthesis
Glycoconjugate Journal, 2001Co-Authors: Anders Bergh, Bengtgoran Magnusson, Ulf Wellmar, Jörgen Ohlsson, Ulf J. NilssonAbstract:The present paper describes the synthesis and use of the hydrophobic squaric decyl ester glycosides in neoglycoconjugate chemistry. The 2-aminoethyl glycosides of α-D-mannopyranose, lactose, globotriose, globotetraose, GM3, and sialyl Lewisx, as well as the 2-(2-aminoethylthio)ethyl glycoside of α-D-mannopyranose, β-D-glucopyranose, and galabiose were reacted with squaric acid didecyl ester to afford the hydrophobic squaric decyl ester glycosides. These glycosides were efficient Reagents for the conjugation to amino-functional microtiter plates, BSA and aminated Sepharose EAH 4B. The decyl ester moiety of the squaric decyl ester glycosides constitutes a traceless hydrophobic tag, which has the major advantage, as compared to the corresponding ethyl esters, that it enables easy purification of the glycosides with silica chromatography and that unreacted excesses glycosides from conjugation reaction mixtures can easily be recovered by means of C18 solid phase extraction.
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Didecyl squarate—A practical amino-reactive Cross-Linking Reagent for neoglycoconjugate synthesis
Glycoconjugate Journal, 2001Co-Authors: Anders Bergh, Bengtgoran Magnusson, Ulf Wellmar, Jörgen Ohlsson, Ulf J. NilssonAbstract:The present paper describes the synthesis and use of the hydrophobic squaric decyl ester glycosides in neoglycoconjugate chemistry. The 2-aminoethyl glycosides of α-D-mannopyranose, lactose, globotriose, globotetraose, GM3, and sialyl Lewis^x, as well as the 2-(2-aminoethylthio)ethyl glycoside of α-D-mannopyranose, β-D-glucopyranose, and galabiose were reacted with squaric acid didecyl ester to afford the hydrophobic squaric decyl ester glycosides. These glycosides were efficient Reagents for the conjugation to amino-functional microtiter plates, BSA and aminated Sepharose EAH 4B. The decyl ester moiety of the squaric decyl ester glycosides constitutes a traceless hydrophobic tag, which has the major advantage, as compared to the corresponding ethyl esters, that it enables easy purification of the glycosides with silica chromatography and that unreacted excesses glycosides from conjugation reaction mixtures can easily be recovered by means of C18 solid phase extraction.