Studies on transfer ribonucleic acid and related compounds. XIII. Synthesis of trinucleoside diphosphates, A-U-A and .EPSILON.A-U-A via a triester intermediate.

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Abstract
ApUpA (XI) and its 1,N6-ethenoadenosine analog, .epsilon.ApUpA (XII) were synthesized by condensation of the protected mononucleotides, 5''-O-monomethoxytrityl-N,2''-O-dibenzoyladenosine 3''-phosphate or 5''-O-monomethoxytrityl-2''-O-benzoyl-1,N6-ethenoadenosine 3''-phosphate with the triester, 2''-O-benzoyluridylyl-(3''-5'')-N,N-2'',3''-O-tetrabenzoyladenosine (VI), in yields of 29 and 24%, respectively. The triester (VI) was prepared by 2 approaches. Best results were obtained by condensation of 5''-O-monomethoxytrityl-2''-O-benzoyluridine 3''-phosphate with N,N-2'',3''-O-tetrabenzoyladenosine in the presence of 2,4,6-triisopropylbenzenesulfonyl chloride and subsequent treatment with .beta.-cyanoethanol. Deprotected trinucleoside diphosphates, XI and XII, were isolated by chromatography on diethylaminoethyl cellulose, and the fluorescence quenching of XII was observed by measurement of the spectra before and after enzymatic digestion of the trimer.

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