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Synlett 1999; 1999(S1): 930-934
DOI: 10.1055/s-1999-3098
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Automated RNA-Synthesis with Photocleavable Sugar and Nucleobase Protecting Groups

Alfred Stutz* , Stefan Pitsch
  • *Organisch-Chemisches Laboratorium der Eidgenössischen Technischen Hochschule, Universitätstrasse 16, CH-8092 Zürich, Switzerland; Fax +41(1)6 32 11 36
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Publication Date:
31 December 1999 (online)

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A new synthetic method for the N-alkyloxycarbonylation of adenine and guanine nucleosides was developed and used for the preparation of RNA-phosphoramidites carrying photolabile sugar and nucleobase protecting groups. From these building blocks, a heptameric oligoribonucleotide was prepared by automated synthesis, followed by detachment from the solid support and photolytic deprotection under mild conditions. The presented strategy allows a simple preparation of 3′-O-aminoacylated RNA-sequences.

phosphoramidites - base-protecting groups - RNA-synthesis - photolabile protection - aminoacylation