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New oligonucleotide analogues based on morpholine subunits joined by oxalyl diamide tether

Authors: 
Abramova TV, Kassakin MF, Lomzov AA, Pyshnyi DV, Silnikov VN
Citation: 
Bioorganic Chemistry 35 (2007) 258–275
Abstract: 
We report on the design, synthesis and some of the properties of the new oligonucleotide analogues based on morpholine nucleoside (MorB) subunits joined by an oxalyl diamide tether instead of a phosphate group. The synthetic strategy and oligomer design are optimized to easily obtain target substances without using protective groups. The dimers HOMorU-Ox-NHMorU, HOMorU-Ox-NHMorA, and uracil containing the hexamer HOMorU-(Ox-NHMorU)5 were synthesized. The structures of all substances were confirmed by 1H, 13C, NMR, and mass spectroscopy. Base stacking interactions in dimers were revealed by CD-spectra data.