Universal 2-(4-nitrophenyl)ethyl and 2-(4-nitrophenyl)ethoxycarbonyl protecting groups for nucleosides and
1Konstanz University, Konstanz, Germany.
Abstract:
A universal blocking group strategy for nucleobases is described, using the 2-(4-nitrophenyl)ethyl (NPE) group for O4-T-, O4-U-, O6-dG-, and O6-G-protection as well as the 2-(4-nitrophenyl)ethoxycarbonyl (NPEOC) group for amino protection in dC, C, dA, A, dG, and G. Conversion into the corresponding 5'-O-dimethoxytrityl derivatives and subsequent phosphitylation to form the fully protected 3'-O-(2-cyanoethyl-N,N-diisopropylphosphoramidites) and 3'-O-(2-(4-nitrophenyl)ethyl-N,N-diisopropylphosphoramidites) produces a new class of interesting building blocks for oligonucleotide synthesis.
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