Dimethylaminomethylene protected purine H-phosphonates in the synthesis of biologically active RNA (24-mer)

Arnold, Luboš; Smrt, Jiří; Zajíček, Jaroslav; Ott, Günther; Schiesswohl, Michael; Sprinzl, Mathias

doi:10.1135/cccc19911948

CCCC > Archive > 1991, Volume 56 > Issue 9 > p. 1948

Dimethylaminomethylene protected purine H-phosphonates in the synthesis of biologically active RNA (24-mer)

Luboš Arnold^a, Jiří Smrt^a, Jaroslav Zajíček^a, Günther Ott^b, Michael Schiesswohl^b and Mathias Sprinzl^b

^a Institute of Organic Chemistry and Biochemistry, Czechoslovak Academy of Sciences, 166 10 Prague 6, Czechoslovakia
^b Laboratorium für Biochemie, Universität Bayreuth, D-8580 Bayreuth, F.R.G.

Abstract

Preparation of 5’-O-(4,4’-dimethoxytrityl)-2’-O-tert-butyldimethylsilyl (tBDMSi) derivatives of N²-dimethylaminomethyleneguanosine (IIIa) and N⁶-dimethylaminomethyleneadenosine (IVa) and their 3’-H-phosphonates (IIIb, IVb) is described. The compounds IIIb and IVb together with corresponding derivatives of uridine (Vb) and N⁴-benzoylcytidine (VIb) were used as synthones in machine assisted synthesis of microhelix^Ala (5’-GGGGCUAUAGCUCUAGCU.CCACCA-3’) (X). The compound X was aminoacylated by means of alanyl-t-RNA synthetase (E.coli).

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Dimethylaminomethylene protected purine H-phosphonates in the synthesis of biologically active RNA (24-mer)

Abstract