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

1 January 1991

journal article
Published by Institute of Organic Chemistry & Biochemistry in Collection of Czechoslovak Chemical Communications

Vol. 56 (9) , 1948-1956
https://doi.org/10.1135/cccc19911948

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).

Keywords

DIMETHOXYTRITYL
PREPARATION OF 5
IIIB
IVB
TERT BUTYLDIMETHYLSILYL
TBDMSI
GGGGCUAUAGCUCUAGCU.CCACCA 3

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