- On surface: O -glycosylation by catalytic microcontact printing
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The generation of carbohydrate patterns on surfaces enables a wide range of analytical and diagnostic applications and efficient methods for carbohydrate immobilization are crucial for this purpose. We report on surface O-glycosylation by catalytic printing as a novel, effective method for the covalent immobilization of carbohydrates in micropatterns. Beside the verification of surface functionalization, the suitability of the generated surface for ligand protein interactions was demonstrated.
- Buhl, Moritz,Traboni, Serena,K?rsgen, Martin,Lamping, Sebastian,Arlinghaus, Heinrich F.,Ravoo, Bart Jan
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supporting information
p. 6203 - 6206
(2017/07/10)
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- A building block approach to the synthesis of a family of S-linked α-1,6-oligomannosides
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The syntheses of α-1,6-S-linked methyl di-, tetra- and hexamannosides are reported. The sulfur linkages are generated through coupling of thiolates (derived from anomeric thioacetates or isothiouronium bromides) with 6-deoxy-6-iodo sugars. Two approaches are detailed that involve [2 + 2 + 2] construction from either the reducing end or the non-reducing end. In constructing from the reducing end, coupling of a disaccharide thioacetate with a 6'-iodo reducing end disaccharide, followed by activation of the resulting tetrasaccharide to a 6'''-iodide, and iterative coupling with the same disaccharide thioacetate afforded the S-linked hexasaccharide, as well as the intermediate di- and tetrasaccharides. On the other hand, construction from the non-reducing end involved coupling of the above disaccharide thioacetate with an anomeric S-trityl protected 6'-iodo disaccharide. The resulting S-trityl tetrasaccharide was converted to a tetrasaccharide thioacetate, which was coupled with the same anomeric S-trityl protected 6'-iodo disaccharide to afford the hexasaccharide, which was elaborated to the methyl thioglycoside. The developed methodology may prove useful for the construction of other S-linked oligosaccharides.
- Belz, Tyson,Williams, Spencer J.
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- DABCO: An efficient promoter for the acetylation of carbohydrates and other substances under solvent-free conditions
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A simple, mild and efficient solvent-free method for the acetylation of carbohydrates, and their partially protected derivatives, as well as non-carbohydrate substances in excellent yields in the presence of 1,4-diazabicyclo[2.2.2]octane (DABCO) is described with the advantage of tolerance to various functional groups, short reaction time and ease of product isolation.
- Ch, Ratnasekhar,Tyagi, Mohit,Patil, Premanand Ramrao,Kartha, K.P. Ravindranathan
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experimental part
p. 5841 - 5846
(2011/12/03)
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- Novel approaches for the synthesis and activation of thio- and selenoglycoside donors
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(Chemical Equation Presented) Alkyl thio-, phenyl seleno-, and phenyl thioglycosides can be prepared through short synthetic sequences based on the generation of glycosyl iodides as versatile intermediates. In addition, a novel cheap combined system (stoichiometric NBS and catalytic Bi(OTf)3) has been developed for rapid and efficient activation of a wide variety of thio- and selenoglycoside donors.
- Valerio, Silvia,Iadonisi, Alfonso,Adinolfi, Matteo,Ravida, Alessandra
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p. 6097 - 6106
(2008/02/09)
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- Streamlined synthesis of per-O-acetylated sugars, glycosyl iodides, or thioglycosides from unprotected reducing sugars
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Solvent-free per-O-acetylation of sugars with stoichiometric acetic anhydride and catalytic iodine proceeds in high yield (90-99%) to give exclusively pyranose products as anomeric mixtures. Without workup, subsequent anomeric substitution employing iodine in the presence of hexamethyldisilane (i.e., TMS-I generated in situ) gives the corresponding glycosyl iodides in 75-95% isolated yield. Alternatively, and without workup, further treatment with dimethyl disulfide or thiol (ethanethiol or thiocresol) gives anomerically pure thioglycosides in more than 75% overall yield.
- Mukhopadhyay, Balaram,Kartha, K.P. Ravindranathan,Russell, David A.,Field, Robert A.
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p. 7758 - 7760
(2007/10/03)
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- Iodine and its interhalogen compounds: Versatile reagents in carbohydrate chemistry v. synthesis of 1,2-trans-linked 1-thioglycosides from the per-o-acetylated glycoses
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Treatment of per-O-acetylated mono- and di-saccharides with (alkyl/arylthio)trimethylsilane and iodine at ambient temperature results in the formation of the corresponding 1,2-trans-1-thioglycosides in very high yield. In the case of higher boiling thiols such as ethanethiol, the reaction can be effectively carried out in the presence of the thiol itself instead of the silylated derivative, but the reaction is not stereospecific. Moreover, in the latter reactions a portion of the starting material remains unchanged even on prolonged reaction. With β-D-glucose pentaacetate (11) as the starting material, its epimerisation occurred during the reaction and therefore the recovered starting material was of α-D-configuration. In addition, the methyl disulphide-hexamethyldisilane system has been found to serve as an effective and cheaper alternative to the expensive (methylthio)-trimethylsilane.
- Kartha, K. P. Ravindranathan,Field, Robert A.
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p. 693 - 702
(2007/10/03)
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- Synthesis of Oligosaccharides Corresponding to the Common Polysaccharide Antigen of Group B Streptococci
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To facilitate mapping of the immunodominant region of the common polysaccharide antigen of group B streptococci, tetrasaccharide 1-O--α-rhamnopyranosyl>-D-glucitol (2) was synthesized in a stepwise fasion
- Pozsgay, Vince,Jennings, Harold J.
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p. 4042 - 4052
(2007/10/02)
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- A Through-process for the Preparation of Methyl Per-O-acetyl 1-Thio-glycosides from Aldoses
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D-Glucose, D-galactose, D-mannose, D-xylose, L-arabinose, L-fucose, L-rhamnose, maltose, cellobiose, lactose, D-glucosamine, D-galactosamine, and D-mannosamine were converted into the corresponding methyl per-O-acetyl 1-thioglycopyranosides by way of a three-step (acetobromination, methylthioation, and acetylation) through-process in a single vessel.
- Koto, Shinkiti,Yoshida, Toyosaku,Takenaka, Kazuhiro,Zen, Shonosuke
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p. 3667 - 3668
(2007/10/02)
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- NEW APPROACH TO ALKYL α-THIOGLYCOSIDES: CIS-HYDROXYLATION OF ALKYL 2,3-DIDEOXY-1-THIO-α-GLYC-2-ENOPYRANOSIDES
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Cis-hydroxylation of alkyl 2,3-dideoxy-1-thio-α-glyc-2-enopyranosides with osmium tetroxide leads to alkyl α-thioglycosides in very good yields.Both hydroxyl groups enter preferentially trans with respect to the bulky substituent at C-1 and/or C-4.Additio
- Priebe, Waldemar,Zamojski, Aleksander
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p. 731 - 739
(2007/10/02)
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