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Nucleic Acids Research, 1994, Vol. 22, No. 1 94-99
© 1994

CHEMISTRY

Evaluation of 2'-hydroxyl protection in RNA-synthesis using the H-phosphonate approach

E. Rozners+, E. Westman and R. Strömberg*

Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University S-10691 Stockholm, Sweden

*To whom correspondence should be addressed

Received September 3, 1993. Accepted November 29, 1993.

A number of different protecting groups were compared with respect to their usefulness for protection of 2'-hydroxyl functions during synthesis of oligoribonucleotides using the H-phosphonate approach. The comparison was between the t-butyldimethylsllyl (t-BDMSi), the o-chlorobenzoyl (o-CIBz), the tetrahydropyranyl (THP), the 1-(2-fluorophenyl)-4-methoxypiperidin-4-yl (Fpmp), the 1-(2-chloro-4-methylphenyl)-4-methoxypiperidin-4-yl (Ctmp), and the 1-{2-chloroeth-oxy)ethyl (Cee) protecting groups. All these groups were tested in synthesis of dodecamers, (Up)11U and (Up)19A, using 5'-O-(4-monomethoxytrityl) or (4,4'-dimethoxytrityl) uridine H-phosphonate building blocks carrying the respective 2'-protection. The performance of the t-BDMSI and o-CIBz derivatives were also compared in synthesis of (Up)19U. The most successful syntheses were clearly those where the t-butyl-dimethylsilyl group was used. The o-chlorobenzoyl group also gave satisfactory results but seems somewhat limited with respect to synthesis of longer oligomers. The results with all tested acetal derivatives (Fpmp, Ctmp, Cee, THP) were much less successful due to some accompanying cleavage of internucleotidic H-phosphonate functions during removal of 5'-O-protection (DMT).

+Present address: Faculty of Chemical Technology, Riga Technical University, Azenes 14/24, Riga LV-1048, Latvia


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