Collect. Czech. Chem. Commun. 1982, 47, 156-166

Synthesis of adenylyl-(2'→5')adenylyl-(2'→5')adenosine

Marat Yu. Karpeiskya, Leon N. Beigelmana, Sergey N. Mikhailova, Nelly Sh. Padyukovaa and Jiří Smrtb

a Institute of Molecular Biology, Academy of Sciences of the USSR, Moscow USSR
b Institute of Organic Chemistry and Biochemistry, Czechoslovak Academy of Sciences, 166 10 Prague 6


Three syntheses of adenylyl-(2'-5')-adenylyl-(2'-5')-adenosine (Ib) are described. In the first, adenosine 2'(3') phosphate is polymerized by the action of diphenylphosphorochloridate, and the 3'-5' internucleotidic linkages and the thermal phosphoryl group removed enzymatically. The second is represented by the triester synthesis starting from 2',3'-di-O-acetyl-N-benzoyladenosine and 5'-O-monomethoxytrityl-3'-O-p-methoxybenzoyl-N-benzoyladenosine 2'(2-cyanoethyl) phosphate (IIc) using 2,4,6-triisopropylbenzenesulfonyl chloride as condensing agent. In the third, 3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)adenosine (V) and 2',3'-di-O-benzoyl-N,N-dibenzoyladenosine serve as the components. The internucleotide bond is synthesized by means of 2-chlorophenylphosphoditriazolide (VI).