1 Chemistry and Biochemistry, Department of Basic Sciences and Environment, Faculty of Life Sciences, Københavns Universitet2 Plant Biochemistry, Department of Plant Biology, Faculty of Life Sciences, Københavns Universitet3 University of Delhi4 Section for Plant Biochemistry, Department of Plant and Environmental Sciences, Faculty of Science, Københavns Universitet5 Rasayan Inc.6 Klinisk Fysiologi og Nuklearmedicin7 NAC, Institut for Fysik og Kemi8 University of Delhi9 Section for Plant Biochemistry, Department of Plant and Environmental Sciences, Faculty of Science, Københavns Universitet
an efficient synthesis of UNA monomer
Lipozyme® TL IM (Theremomyces lanuginosus lipase immobilized on silica) in toluene catalyzes the acylation of the 2( )'-OH over the 3( )'-OH group in 5( )'-O-(4,4( )'-dimethoxytrityl)-2( )',3( )'-secouridine (5( )'-O-DMT-2( )',3( )'-secouridine) in a highly selective fashion in moderate to almost quantitative yields. The turn over during benzoyl transfer reactions mediated by vinyl benzoate or benzoic anhydride was faster than in acyl transfer reactions with vinyl acetate or C(1) to C(5) acid anhydrides; except in the case of butanoic anhydride. The 2( )'-O-benzoyl-5( )'-O-DMT-2( )',3( )'-secouridine obtained by Lipozyme® TL IM catalyzed benzoylation of 5( )'-O-DMT-2( )',3( )'-secouridine was successfully converted into its 3( )'-O-phosphoramidite derivative in satisfactory yield, which is a building block for the preparation of oligonucleotides containing the uracil monomer of UNA (unlocked nucleic acid).
Nucleosides, Nucleotides and Nucleic Acids, 2012, Vol 31, Issue 12, p. 831-840