ol500668n_si_002.pdf (4.72 MB)
Efficient Functionalization of Oligonucleotides by New Achiral Nonnucleosidic Monomers
journal contribution
posted on 2014-06-06, 00:00 authored by Maxim
S. Kupryushkin, Mikhail D. Nekrasov, Dmitry A. Stetsenko, Dmitrii V. PyshnyiA novel
synthetic strategy has been designed for preparation of achiral nonnucleosidic
phosphoramidite monomers for automated solid-phase oligonucleotide
synthesis. It is based on O-DMTr-protected 4-(2-hydroxyethyl)-morpholine-2,3-dione
as the key compound and a family of building blocks obtained by its
ring-opening by primary aliphatic amines. A series of nonnucleosidic
phosphoramidites containing various side-chain functionalities was
synthesized, and corresponding oligodeoxyribonucleotides incorporating
modified units in single or multiple positions along the chain were
prepared.
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building blocksseriesNew Achiral Nonnucleosidic MonomersA novelhydroxyethylaliphatic aminesstrategyOligonucleotidesynthesisfunctionalitienonnucleosidic phosphoramiditesoligonucleotidecompoundachiral nonnucleosidic phosphoramidite monomersEfficient Functionalizationpreparationoligodeoxyribonucleotide
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