Collect. Czech. Chem. Commun. 1991, 56, 1948-1956

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

Luboš Arnolda, Jiří Smrta, Jaroslav Zajíčeka, Günther Ottb, Michael Schiesswohlb and Mathias Sprinzlb

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.


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 microhelixAla (5’-GGGGCUAUAGCUCUAGCU.CCACCA-3’) (X). The compound X was aminoacylated by means of alanyl-t-RNA synthetase (E.coli).