title: Efficient functionalization of oligonucleotides by new achiral nonnucleosidic monomers.
abstract: A 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.
authors.affiliation: Institute of Chemical Biology and Fundamental Medicine, Siberian Branch of the Russian Academy of Sciences , 8 Lavrentiev Avenue, Novosibirsk 630090, Russia.
authors.forename: Maxim S
authors.initials: MS
authors.lastname: Kupryushkin
authors.forename: Mikhail D
authors.initials: MD
authors.lastname: Nekrasov
authors.forename: Dmitry A
authors.initials: DA
authors.lastname: Stetsenko
authors.forename: Dmitrii V
authors.initials: DV
authors.lastname: Pyshnyi
mesh_terms: D000588:Amines / Q000737:chemistry*; D015394:Molecular Structure; D009838:Oligodeoxyribonucleotides / Q000737:chemistry*; D009841:Oligonucleotides / Q000138:chemical synthesis* / Q000737:chemistry*; D009943:Organophosphorus Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D060327:Solid-Phase Synthesis Techniques
chemical_list: D000588:Amines; D009838:Oligodeoxyribonucleotides; D009841:Oligonucleotides; D009943:Organophosphorus Compounds; C434331:phosphoramidite