125158-52-3Relevant articles and documents
Application of lipases to the regioselective synthesis of sucrose fatty acid monoesters
Sarney, Douglas B.,Barnard, Mark J.,MacManus, David A.,Vulfson, Evgeny N.
, p. 1481 - 1487 (1996)
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.
Modulating the activity of oligonucleotides by carbohydrate conjugation: Solid phase synthesis of sucrose-oligonucleotide hybrids
Adinolfi, Matteo,De Napoli, Lorenzo,Fabio, Giovanni Di,Iadonisi, Alfonso,Montesarchio, Daniela
, p. 1879 - 1886 (2007/10/03)
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.
