Chemical Synthesis of Guanosine Oligoribonucleotides: The Synthesis of N^2-Benzoyl-2'-O-tetrahydropyranylguanosine and N^2-benzoyl-2'-O-tetrahydropyranyl-5'-O-triphenylmethoxyacetylguanosine

Abstract

<p>Synthesis of oligoribonucleotides of defined sequence and length corresponding to regions within biologically active RNA species is an attractive proposition. The specific objective is the synthesis of oligoribonucleotides corresponding to the amino acyl synthetase acceptor stem region of yeast tRNA^ala. This sequence contains many guanosine residues but guanosine derivatives necessary for incorporation into a general synthesis were not at hand. The synthesis of N^2-benzoyl-2'-O- tetrahydropyranylguanosine (VI) and N^2-benzoyl-2'-0-tetrahydropyranyl- 5'-0-triphenylmethoxyacetylguanosine (VIII) are carried out. Their utilization in the synthesis of guanylyl(3'-5')guanosine (GpG) is described. These precursors, VI and VIII, can now participate in a fragment coupling synthesis of the duplex corresponding to the acceptor stem region of yeast tRNA^ala.</p>