The Experts below are selected from a list of 300 Experts worldwide ranked by ideXlab platform
Olivier R. Martin - One of the best experts on this subject based on the ideXlab platform.
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A practical approach to Dideoxy-1,4- and 1,5-iminopentitols from protected sugar hemiacetals.
Carbohydrate research, 2019Co-Authors: Justyna Jaszczyk, Cyril Nicolas, Chloé Cocaud, Olivier R. MartinAbstract:The convenient and straightforward preparation of dideoxy-1,4- and 1,5-iminopentitol derivatives from protected sugar hemiacetals by way of N-tert-butanesulfinyl Glycosylamines and open-chain aminoalditols is reported. The synthetic procedure is a method of choice for the making of these important scaffolds of biological interest.
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Glycoside Mimics from Glycosylamines: Recent Progress.
Molecules (Basel Switzerland), 2018Co-Authors: Cyril Nicolas, Olivier R. MartinAbstract:Glycosylamines are valuable sugar derivatives that have attracted much attention as synthetic intermediates en route to iminosugar-C-glycosyl compounds. Iminosugars are among the most important glycomimetics reported to date due to their powerful activities as inhibitors of a wide variety of glycosidases and glycosyltransferases, as well as for their use as pharmacological chaperones. As they provide ready access to these important glycoside mimics, we have reviewed the most significant Glycosylamine-based methodologies developed to date, with a special emphasis on the literature reported after 2006. The groups of substrates covered include N-alkyl- and N-benzyl-Glycosylamines, N-glycosylhydroxylamines, N-(alkoxycarbonyl)-, and N-tert-butanesulfinyl-Glycosylamines.
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Synthesis and Reactivity of N-tert-Butanesulfinyl Glycosylamines
European Journal of Organic Chemistry, 2015Co-Authors: Chloé Cocaud, Cyril Nicolas, Alexandre Bayle, Thomas Poisson, Xavier Pannecoucke, Olivier R. MartinAbstract:A study of the preparation and of the reactivity of N-tert-butanesulfinyl Glycosylamines is reported for the first time. As they react readily as latent imine equivalents with a variety of carbon nucleophiles, these new carbohydrate derivatives constitute very useful precursors for the diastereoselective synthesis of bioactive compounds such as iminosugar-C-glycosides.
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Synthesis and Reactivity of N‐tert‐Butanesulfinyl Glycosylamines
European Journal of Organic Chemistry, 2015Co-Authors: Chloé Cocaud, Cyril Nicolas, Alexandre Bayle, Thomas Poisson, Xavier Pannecoucke, Olivier R. MartinAbstract:A study of the preparation and of the reactivity of N-tert-butanesulfinyl Glycosylamines is reported for the first time. As they react readily as latent imine equivalents with a variety of carbon nucleophiles, these new carbohydrate derivatives constitute very useful precursors for the diastereoselective synthesis of bioactive compounds such as iminosugar-C-glycosides.
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One-step synthesis of N-protected Glycosylamines from sugar hemiacetals.
Carbohydrate Research, 2008Co-Authors: Virginie Liautard, Christelle Pillard, Valérie Desvergnes, Olivier R. MartinAbstract:Protected pentofuranose, hexofuranose and hexopyranose hemiacetals were found to react efficiently with amines carrying a deactivating group (alkoxycarbonyl, tosyl or phosphoryl group) in the presence of a Lewis acid to give the corresponding, stable Glycosylamines. Such Glycosylamine derivatives are useful substrates for further elaboration into nitrogen-containing natural products and carbohydrate mimetics.
Chloé Cocaud - One of the best experts on this subject based on the ideXlab platform.
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A practical approach to Dideoxy-1,4- and 1,5-iminopentitols from protected sugar hemiacetals.
Carbohydrate research, 2019Co-Authors: Justyna Jaszczyk, Cyril Nicolas, Chloé Cocaud, Olivier R. MartinAbstract:The convenient and straightforward preparation of dideoxy-1,4- and 1,5-iminopentitol derivatives from protected sugar hemiacetals by way of N-tert-butanesulfinyl Glycosylamines and open-chain aminoalditols is reported. The synthetic procedure is a method of choice for the making of these important scaffolds of biological interest.
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Synthesis and Reactivity of N-tert-Butanesulfinyl Glycosylamines
European Journal of Organic Chemistry, 2015Co-Authors: Chloé Cocaud, Cyril Nicolas, Alexandre Bayle, Thomas Poisson, Xavier Pannecoucke, Olivier R. MartinAbstract:A study of the preparation and of the reactivity of N-tert-butanesulfinyl Glycosylamines is reported for the first time. As they react readily as latent imine equivalents with a variety of carbon nucleophiles, these new carbohydrate derivatives constitute very useful precursors for the diastereoselective synthesis of bioactive compounds such as iminosugar-C-glycosides.
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Synthesis and Reactivity of N‐tert‐Butanesulfinyl Glycosylamines
European Journal of Organic Chemistry, 2015Co-Authors: Chloé Cocaud, Cyril Nicolas, Alexandre Bayle, Thomas Poisson, Xavier Pannecoucke, Olivier R. MartinAbstract:A study of the preparation and of the reactivity of N-tert-butanesulfinyl Glycosylamines is reported for the first time. As they react readily as latent imine equivalents with a variety of carbon nucleophiles, these new carbohydrate derivatives constitute very useful precursors for the diastereoselective synthesis of bioactive compounds such as iminosugar-C-glycosides.
G. Russo - One of the best experts on this subject based on the ideXlab platform.
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Efficient Synthesis of Unsymmetrical Ureido-Linked Disaccharides
'Wiley', 2004Co-Authors: D. Prosperi, S. Ronchi, L. Lay, A. Rencurosi, G. RussoAbstract:Five nonsymmetrical urea-linked disaccharides, in which two glycopyranoside units are bound at the 1 2, 1 4, and 1-6 positions, were efficiently synthesized. A mild and safe procedure, in which glycosyl isocyanates were coupled with a Glycosylamine, was employed
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efficient synthesis of unsymmetrical ureido linked disaccharides
European Journal of Organic Chemistry, 2004Co-Authors: D. Prosperi, S. Ronchi, A. Rencurosi, G. RussoAbstract:Five nonsymmetrical urea-linked disaccharides, in which two glycopyranoside units are bound at the 1⇄2, 1⇄4, and 1⇄6 positions, were efficiently synthesized. A mild and safe procedure, in which glycosyl isocyanates were coupled with a Glycosylamine, was employed. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)
Cyril Nicolas - One of the best experts on this subject based on the ideXlab platform.
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A practical approach to Dideoxy-1,4- and 1,5-iminopentitols from protected sugar hemiacetals.
Carbohydrate research, 2019Co-Authors: Justyna Jaszczyk, Cyril Nicolas, Chloé Cocaud, Olivier R. MartinAbstract:The convenient and straightforward preparation of dideoxy-1,4- and 1,5-iminopentitol derivatives from protected sugar hemiacetals by way of N-tert-butanesulfinyl Glycosylamines and open-chain aminoalditols is reported. The synthetic procedure is a method of choice for the making of these important scaffolds of biological interest.
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Glycoside Mimics from Glycosylamines: Recent Progress.
Molecules (Basel Switzerland), 2018Co-Authors: Cyril Nicolas, Olivier R. MartinAbstract:Glycosylamines are valuable sugar derivatives that have attracted much attention as synthetic intermediates en route to iminosugar-C-glycosyl compounds. Iminosugars are among the most important glycomimetics reported to date due to their powerful activities as inhibitors of a wide variety of glycosidases and glycosyltransferases, as well as for their use as pharmacological chaperones. As they provide ready access to these important glycoside mimics, we have reviewed the most significant Glycosylamine-based methodologies developed to date, with a special emphasis on the literature reported after 2006. The groups of substrates covered include N-alkyl- and N-benzyl-Glycosylamines, N-glycosylhydroxylamines, N-(alkoxycarbonyl)-, and N-tert-butanesulfinyl-Glycosylamines.
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Synthesis and Reactivity of N-tert-Butanesulfinyl Glycosylamines
European Journal of Organic Chemistry, 2015Co-Authors: Chloé Cocaud, Cyril Nicolas, Alexandre Bayle, Thomas Poisson, Xavier Pannecoucke, Olivier R. MartinAbstract:A study of the preparation and of the reactivity of N-tert-butanesulfinyl Glycosylamines is reported for the first time. As they react readily as latent imine equivalents with a variety of carbon nucleophiles, these new carbohydrate derivatives constitute very useful precursors for the diastereoselective synthesis of bioactive compounds such as iminosugar-C-glycosides.
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Synthesis and Reactivity of N‐tert‐Butanesulfinyl Glycosylamines
European Journal of Organic Chemistry, 2015Co-Authors: Chloé Cocaud, Cyril Nicolas, Alexandre Bayle, Thomas Poisson, Xavier Pannecoucke, Olivier R. MartinAbstract:A study of the preparation and of the reactivity of N-tert-butanesulfinyl Glycosylamines is reported for the first time. As they react readily as latent imine equivalents with a variety of carbon nucleophiles, these new carbohydrate derivatives constitute very useful precursors for the diastereoselective synthesis of bioactive compounds such as iminosugar-C-glycosides.
Thomas Norberg - One of the best experts on this subject based on the ideXlab platform.
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Reversible derivatization of sugars with carbobenzyloxy groups and use of the derivatives in solution-phase enzymatic oligosaccharide synthesis.
Carbohydrate research, 2021Co-Authors: Thomas Norberg, Elisabet Kallin, Ola BlixtAbstract:Abstract Simple protocols for attaching and detaching carbobenzyloxy (Cbz) groups at the reducing end of sugars was developed. Briefly, lactose was converted into its Glycosylamine, which was then acylated with carbobenzyloxy chloride in high overall yield. The obtained lactose Cbz derivative was used in sequential glycosylations using glycosyltransferases and nucleotide sugars in aqueous buffers. Isolation of the reaction products after each step was by simple C-18 solid-phase extraction. The Cbz group was removed by catalytic hydrogenolysis or catalytic transfer hydrogenation followed by in situ Glycosylamine hydrolysis. In this way, a trisaccharide (GlcNAc-lactose), a human milk tetrasaccharide (LNnT), and a human milk pentasaccharide (LNFPIII) were prepared in a simple and efficient way.
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Enzymatic glycosylation of reducing oligosaccharides linked to a solid phase or a lipid via a cleavable squarate linker
Carbohydrate Research, 1999Co-Authors: Ola Blixt, Thomas NorbergAbstract:Reducing oligosaccharides were converted into their corresponding Glycosylamines, and these were reacted with 3,4-diethoxy-3-cyclobuten-1,2-dione (squaric acid diethyl ester). The resulting derivatives could be linked to amino-functionalized lipids, solids, or proteins. Treatment of the obtained lipid or solid conjugates with aqueous bromine or, alternatively, with ammonia-ammonium borate cleaved the linkage and regenerated the oligosaccharide Glycosylamines, which were in turn rapidly hydrolyzed to the reducing oligosaccharides. To demonstrate the usefulness of this linkage in enzymatic oligosaccharide synthesis, lactose was linked to a lipid or a solid phase, the obtained conjugates were then subjected to two enzymatic glycosylations (either consecutively or 'one-pot'). The resulting materials were then cleaved to give, in both cases, the expected reducing tetrasaccharide (lacto-N-neotetraose) in good yield.
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Derivatization Procedures for Reducing Oligosaccharides, Part 4: Use of Glycosylamines in a Reversible Derivatization of Oligosaccharides with the 9-Fluorenylmethoxycarbonyl Group, and Hplc Separations of the Derivatives
Journal of Carbohydrate Chemistry, 1991Co-Authors: Elisabeth Kallin, Hans Lönn, Thomas Norberg, Torbjörn Sund, Mons LundqvistAbstract:ABSTRACT A new, reversible derivatization procedure for reducing oligosaccharides was developed. Reaction of the model compound lacto-N-tetraose (β-D-Gal-(1→3)-β-D-GlcNAc-(1→3)-β-D-Gal-(1→4)-D-Glc) with aqueous ammonium bicarbonate gave the corresponding β-Glycosylamine, which was reacted with fluorenylmethoxycarbonyl chloride to give an N-fluorenyl-methoxycarbonyl β-Glycosylamine (FMOC derivative). The free oligosaccharide could be recovered in high yield from the FMOC derivative by brief treatment with 15% aqueous ammonia. Complex oligosaccharide mixtures from human milk were derivatized with the new procedure, and excellent separations of the derivatives on straight-phase silica HPLC columns were achieved.