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Nucleic Acids Research, 1991, Vol. 19, No. 4 733-738
© 1991

CHEMISTRY

New synthetic routes to synthons suitable for 2'-O-allyloligoribonucleotide assembly

Brian S. Sproat*, Adolfo M. Iribarre1, Ramon Guimil Garcia and Barbro Beijer

European Molecular Biology Laboratory Postfach 10.2209, D-6900 Heidelberg, FRG 1Instituto di Ricerche di Biologia Molecolare Via Pontina, Km 30.600, 00040 Pomezia, Italy

* To whom correspondence should be addressed

Received December 4, 1990. Accepted January 23, 1991.

New synthetic routes have been devised for the high yield preparation of protected 2'-O-allylribonucleoside- 3'4-phosphoramldites, exemplified by the ribonucleosides guanosine and 2,6-diaminopurine riboside (2-amlnoadenosine). Key features are the use of versatile intermediates and an easy allylation step. The development of a novel synthon based on 2'O-allyl- 2,6-diaminopurine riboslde enables short 2'O-allyloligoribonucieotide probes to be synthesized with adenine replaced by 2-aminoadenlne. Thus very stable hybrids wtth complementary RNA target sequences can be formed due to the formation of the three hydrogen bond 2-amlno A-U base pairs.


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