- Application of lipases to the regioselective synthesis of sucrose fatty acid monoesters
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A regioselective synthesis of 6′-O-acyl sucrose monoesters has been developed through the lipase-catalyzed esterification of sucrose acetals with fatty acids in both organic solvents and under solvent-free conditions. The products were obtained in overall yields of 20-27% after hydrolysis of the isopropylidene groups with aqueous acids. The strict selectivity of the enzymes used also enabled the preparation of a monoester fraction that was highly enriched in 6-O-acyl sucrose. This was accomplished by lipase-catalyzed transesterification of sucrose monoesters, prepared by conventional chemical methods, in propan-2-ol. After removal of the transesterification products (sucrose and fatty acid isopropyl esters) and column chromatography on silica gel, the obtained monoester product contained 80% of the single regioisomer, 6-O-acyl sucrose.
- Sarney, Douglas B.,Barnard, Mark J.,MacManus, David A.,Vulfson, Evgeny N.
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- Synthesis and biophysical characterization of G-rich oligonucleotides conjugated with sugar-phosphate tails
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A number of 5′-and 3′-glycoconjugates of the oligonucleotide 5′d(TGGGAG)3′ have been synthesized, exploiting fully automated, online phosphoramidite-based solid phase strategy, as potential anti-HIV-1 agents. The thermodynamic stability of the resulting quadruplexes has been investigated by thermal denaturation studies, via a detailed CD Q1 analysis. Copyright Taylor & Francis Group, LLC.
- D'Onofrio,Erra,Di Fabio,Iadonisi,Petraccone,De Napoli,Barone,Balzarini,Giancola,Montesarchio
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p. 1225 - 1229
(2008/09/20)
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- Modulating the activity of oligonucleotides by carbohydrate conjugation: Solid phase synthesis of sucrose-oligonucleotide hybrids
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In order to expand the repertoire of available oligosaccharide- oligonucleotide hybrids, the on-line solid phase synthesis of oligonucleotides conjugated at the 3′- and/or 5′-end with a preformed disaccharide unit has been performed. The key compound in the synthetic scheme described here is an appropriate phosphoramidite derivative of fully protected sucrose, used in association with a solid support functionalized with DMT-protected sucrose. The sucrose units at both ends of selected oligonucleotide sequences were shown to increase their chemical and enzymatic stability, while not interfering with duplex formation and with the ability of G-rich sequences to adopt a quadruplex structure.
- Adinolfi, Matteo,De Napoli, Lorenzo,Fabio, Giovanni Di,Iadonisi, Alfonso,Montesarchio, Daniela
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p. 1879 - 1886
(2007/10/03)
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- Dimethylformamide-dimethyl sulfate adduct as an effective reagent for the preparation of benzylideneacetals of mono- and disaccharides
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A simple and effective method for the preparation of cyclic 4,6-benzylideneacetals of mono and disaccharides has been developed.It involves treatment of the sugar with benzaldehyde in dimethyl sulfate and dry DMF under nitrogen atmosphere at room temperature.
- Mani, N. S.
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p. 602 - 603
(2007/10/02)
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