Modulating the activity of oligonucleotides by carbohydrate conjugation: solid phase synthesis of sucrose-oligonucleotide hybrids

Organic & Biomolecular Chemistry
Matteo AdinolfiDaniela Montesarchio

Abstract

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.

Citations

Feb 3, 2007·Glycoconjugate Journal·Hongbin Yan, Kha Tram
Dec 11, 2007·Nucleosides, Nucleotides & Nucleic Acids·J D'OnofrioD Montesarchio
Sep 25, 2015·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Domenica MusumeciDaniela Montesarchio
Mar 17, 2015·International Journal of Pharmaceutics·Giovanni N RovielloValentina Roviello
Mar 25, 2006·Organic & Biomolecular Chemistry·Yashveer SinghPascal Dumy
Jun 19, 2013·Current Protocols in Nucleic Acid Chemistry·Andrei P Guzaev
Nov 15, 2013·Chemistry : a European Journal·J Sebastian TemmeIsaac J Krauss
Jan 31, 2008·The Journal of Organic Chemistry·María Sanchez-RosellóScott J Miller
Nov 9, 2007·The Journal of Organic Chemistry·Cinzia CoppolaDaniela Montesarchio
Aug 30, 2017·ACS Applied Materials & Interfaces·Claudia RiccardiDaniela Montesarchio

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