title: Oligonucleotide functionalization by a novel alkyne-modified nonnucleosidic reagent obtained by versatile building block chemistry.
abstract: A convenient synthetic strategy has been designed to prepare an alkyne-modified synthon for automated DNA synthesis. It is based on the key O-DMTr-protected 4-(2-hydroxyethyl)morpholin-2,3-dione and building blocks obtained by its functionalization by various aliphatic amines. A respective nonnucleosidic phosphoramidite monomer containing a terminal alkyne in the side-chain was synthesized, and corresponding oligothymidylates incorporating the modification in various positions were prepared. The presence of the alkyne group was confirmed by Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC) between the functionalized oligonucleotide and an azide derivative of 7-nitro-2,1,3-benzoxadiazole.
authors: Institute of Chemical Biology and Fundamental Medicine, Siberian Branch of the Russian Academy of Sciences, Novosibirsk, Russia.
authors: Maxim S
authors: MS
authors: Kupryushkin
authors: Dmitrii A
authors: DA
authors: Konevetz
authors: Svetlana V
authors: SV
authors: Vasilyeva
authors: Anastasia S
authors: AS
authors: Kuznetsova
authors: Dmitry A
authors: DA
authors: Stetsenko
authors: Dmitrii V
authors: DV
authors: Pyshnyi
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D001386:Azides / Q000737:chemistry; D057930:Click Chemistry; D009841:Oligonucleotides / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism; D009943:Organophosphorus Compounds / Q000737:chemistry; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization
chemical_list: D000480:Alkynes; D001386:Azides; D009841:Oligonucleotides; D009943:Organophosphorus Compounds; C434331:phosphoramidite