Premium
Phthalimide–Oxy Derivatives for 3′‐ or 5′‐Conjugation of Oligonucleotides by Oxime Ligation and Circularization of DNA by “Bis‐ or Tris‐Click” Oxime Ligation
Author(s) -
Meyer Albert,
Vasseur JeanJacques,
Dumy Pascal,
Morvan François
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201701317
Subject(s) - oligonucleotide , oxime , phthalimide , combinatorial chemistry , chemistry , chemical ligation , conjugated system , ligation , dna , oligonucleotide synthesis , polymer chemistry , organic chemistry , biology , biochemistry , microbiology and biotechnology , peptide , polymer
A solid support and two phosphoramidites exhibiting a phthalimide–oxy group were synthesized. First, after treatment with hydrazine, the resulting 5′‐ and 3′‐oxyamine oligonucleotides were conjugated with aldehyde derivatives by oxime ligation. Second, oligonucleotides exhibiting an oxyamine at each end were circularized by means of different dialdehydes. Cyclic oligonucleotides of different lengths (9 to 31‐mer) were rapidly obtained without the need of a template. Finally, a bicyclic oligonucleotide was synthesized starting form an oligonucleotide bearing three oxyamines, which reacted with a trialdehyde to form three oxime ligations.