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Nucleic Acids Research, 1992, Vol. 20, No. 19 5159-5166
© 1992

CHEMISTRY

Chemical synthesis of a biologically active natural tRNA with its minor bases

Didier Gasparutto, Thierry Livache1, Hervé Bazin1, Anne-Marie Duplaa, André Guy, Alexander Khorlin+, Didier Molko, André Roget1 and Robert Téoule*

Service d'Etudes des Systémes et Architectures Moléculaires, Département de Recherche Fondamentale de la Matiére Condensée 85X, 38041 Grenoble Cedex, France 1Laboratoire des Sondes Moléculaires, CIS Bio International, Centre d'Etudes Nucléaires de Grenoble 85X, 38041 Grenoble Cedex, France

* To whom correspondence should be addressed

Received May 29, 1992. Revised August 19, 1992. Accepted August 19, 1992.

The complete chemical synthesis of an E.coli tRNAAla with its specific minor nucleosides, dlhydrouridine, ribothymidine and pseudouridine, is reported. The method makes use of protected 2'-O-tertiobutyldi-methylsilyl-ribonucleoside-3'-O-(2-cyanoethyl-N-ethyl-N-methyl)phosphoramidites. The exocyclic amino functions of the bases were protected by the phenoxy-acetyl group for purines and acetyl for cytosine. The assembling has been performed on a silica support with coupling yield better than 98% within 2 min of condensation. TriethylamJne trls-hydrofluoride allowed a clean and complete deprotection of the tBDMS groups. The synthetic tRNAAla has been transcribed into cDNA by reverse transcriptase and sequenced. With E.coli alanyl-tRNA synthetase the alanyl acceptance activity and kcat/Km were 672 pmol/A290 and 6x104M-1s-1, respectively.

+ Visiting professor: Engelhardt Institute of Molecular Biology, Russian Academy of Sciences, Moscow, Russia


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