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Functionalization of 2″‐C‐(Piperazinomethyl)‐2′,3′‐BcNA (Bicyclic Nucleic Acids) with Pyren‐1‐ylcarbonyl Units
Authors:Morten Borre Hansen  Nicolai Krog Andersen  Michael Raunkjær  Per Trolle Jørgensen  Jesper Wengel
Affiliation:1. Nucleic Acid Center, Department of Physics, Chemistry and Pharmacy, University of Southern Denmark, Campusvej 55, DK‐5230 Odense M (phone: +45‐65‐502510);2. Present address: Novo Nordisk, Novo Nordisk Park, DK‐2760 M?l?v.;3. Present address: Novo Nordisk, Niels Steensens vej 1, DK‐2820, Gentofte.
Abstract:Herein, we describe the incorporation of 2″‐C‐(piperazinomethyl)‐2′,3′‐BcNA (Bicyclic Nucleic Acids) into oligonucleotides via phosphoramidite chemistry and their subsequent solid‐phase functionalization with pyren‐1‐ylcarbonyl units after oligonucleotide synthesis. Thermal denaturation measurements showed that one modification led to increased thermal stability of the resulting duplex, and that two modifications could be incorporated in close proximity without decreasing the duplex stability (compared to the duplex stability of unmodified RNA). Fluorescence studies of the modified duplexes revealed that the structure and intensity of the fluorescence spectra were largely sequence‐dependent. Furthermore, molecular‐modeling studies showed that the pyrene moieties are placed in the major groove, and that the configuration at C(2″) is important for the thermal stability of the duplex.
Keywords:Oligonucleotides  Bicyclic nucleic acids (BcNAs)  Fluorescence  Nucleic acids  Pyrene  Thermal stability  Molecular modeling
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