Synthesis of monomers bearing at the 2'-position cyanomethoxycarbonyl group for phosphoramidite oligonucleotide synthesis.
A novel series of phosphoroamidites for the synthesis of 2-modified oligonucleotides was designed and synthesized on the base of 2'-amino uridine and 2'-amino arabinoadenosine. The amino groups in these compounds were acidified by bis-cyanomethyl esters of different dicarbonic acids. Generated reactive linker groups containing cyanomethoxycarbonyl groups are stable under conditions of oligonucleotide synthesis but could be easily functionalised in post-synthetic stage by treatment with compounds bearing primary amino groups.
Vasilyeva
Svetlana V
SV
Novosibirsk Institute of Bioorganic Chemistry, Novosibirsk, Russia. vasilieva_2001@ngs.ru
Abramova
Tatyana V
TV
Silnikov
Vladimir N
VN
D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry; D019906:Nuclear Magnetic Resonance, Biomolecular; D009841:Oligonucleotides / Q000138:chemical synthesis* / Q000737:chemistry; D010756:Phosphoric Acids / Q000138:chemical synthesis* / Q000737:chemistry; D013056:Spectrophotometry, Ultraviolet
D000577:Amides; D009841:Oligonucleotides; D010756:Phosphoric Acids; C011067:phosphoramidic acid