Modulating the activity of oligonucleotides by carbohydrate conjugation: solid phase synthesis of sucrose-oligonucleotide hybrids.
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
M
Dipartimento di Chimica Organica e Biochimica, Università degli Studi di Napoli Federico II, Complesso Universitario di Monte S. Angelo, via Cynthia, 4, I-80126 Naples, Italy.
De Napoli
Lorenzo
L
Di Fabio
Giovanni
G
Iadonisi
Alfonso
A
Montesarchio
Daniela
D
D002851:Chromatography, High Pressure Liquid; D002942:Circular Dichroism; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009690:Nucleic Acid Conformation; D009841:Oligonucleotides / Q000138:chemical synthesis* / Q000737:chemistry*; D013395:Sucrose / Q000737:chemistry*
D009841:Oligonucleotides; D013395:Sucrose