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Functionalization of 2″‐ C ‐(Piperazinomethyl)‐2′,3′‐BcNA (Bicyclic Nucleic Acids) with Pyren‐1‐ylcarbonyl Units
Author(s) -
Borre Hansen Morten,
Krog Andersen Nicolai,
Raunkjær Michael,
Trolle Jørgensen Per,
Wengel Jesper
Publication year - 2014
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201400141
Subject(s) - chemistry , duplex (building) , phosphoramidite , oligonucleotide , nucleic acid , bicyclic molecule , thermal stability , surface modification , pyrene , fluorescence , stereochemistry , rna , combinatorial chemistry , dna , organic chemistry , biochemistry , physics , quantum mechanics , gene
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.