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Nucleic Acids Research, 1978, Vol. 5, No. 6 1889-1905
© 1978

Articles

The chemical synthesis of the anticodon loop of an eukaryotic initiator tRNA containing the hypermodified nucleoside N6-/N-threonylcarbonyl/-adenosine/t6A/1

R.W. Adamiak, E. Biala, K. Grzéskowiak, R. Kierzek, A. Kraszewski, W.T. Markiewicz, J. Okupniak, J. Stawinski and M. Wiewiórowski

Department of Stereochemistry of Natural Products, Institute of Organic Chemistry, Polish Academy of Sciences Noskowskiego 12/14,61-704 Poznan, Poland

Received April 10, 1978. In this work, the first example of chemical synthesis of oligoribonucleotide containing the hypermodified nucleoside N6-/N-threonylcarbonyl/-adenosine/t6A/ is presented.

Synthesis of the heptamer C-C-C-A-U-t6A-A IX, the sequence of which is related to the anticodon loop of the initiator tRNA from yellow lupine, was achieved by: /i/ phosphotriester block synthesis of suitably protected heptamer VI containing an adenosine unit with a free exo-NH2 group, /ii/ highly effective "one-flask" procedure for the transformation of the free exo-NH2 group of adenosine unit of heptamer VI into a N,N'-disubstituted urea system of t6A of heptamer VII /hypermodification/, and /iii/ final deprotection of VIII /32% total yield/ with the use of a new approach for simultaneous hydrogenolysis /Pd0-hydrogen-pyridine/ of the p-nitrobenzyl group and 2,2,2-trichloroethyl groups from carboxyl function of t6A and internucleotide phosphates respectively.


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E. Kierzek and R. Kierzek
The synthesis of oligoribonucleotides containing N6-alkyladenosines and 2-methylthio-N6-alkyladenosines via post-synthetic modification of precursor oligomers
Nucleic Acids Res., August 1, 2003; 31(15): 4461 - 4471.
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