Collect. Czech. Chem. Commun. 1996, 61, 389-403

Preparation of 1'-C Deuterated Synthons for RNA Synthesis by H-Phosphonate Method Aiming at Two-Dimensional NMR Secondary Structure Studies

Luboš Arnolda, Martina Pressováa, David Šamana, Martin Vogtherrb and Stefan Limmerb

a Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, 166 10 Prague 6, Czech Republic
b Laboratorium für Biochemie, Universität Bayreuth, D-95440 Bayreuth, Germany


1'-C Deuterated H-phosphonate synthons were prepared via a 12-step procedure starting from [1'-2H]ribose. The procedure included nucleosidation of 1'-O-acetyl-2',3',5'-O-tribenzoyl[1'-2H]ribose with appropriately protected nucleobases and preparation of nucleoside-H-phosphonates by slightly modified described procedures. The automated RNA synthesis of 5'-G*C*U*A*U*UUAU-3' and 3'-AC*G*A*U*A*AAGU-5' was performed on a Gene Assembler Plus DNA-synthesizer. These specifically deuterated oligoribonucleotides were subsequently compared with the corresponding non-deuterated sequences using 2D-NMR NOESY spectra. Specific deuterium incorporation resulted in the expected simplification of spectral pattern.

Keywords: [1'-2H]Ribose; Nucleoside-H-phosphonates; Oligoribonucleotides, deuterated.