Efficient Release of Base-Sensitive Oligonucleotides from Solid Supports using Fluoride Ions

European Journal of Organic Chemistry (Impact Factor: 3.15). 05/2009; DOI: 10.1002/ejoc.200801275

ABSTRACT With the aim to prepare biolabile oligoribonucleotides that are partially or fully base-sensitive 2′-O-pivaloyloxymethyl functionalized, we investigated the cleavage of a silyl-type linker and a Q-linker anchored to a solid support under several fluoride ion conditions. Thus, an original fluoride ion treatment was perfected to release oligonucleotides bearing base-sensitive modifications from solid supports without affecting them and with high efficiency. Chimeric oligouridylates containing both 2′-OH and 2′-O-PivOM groups were obtained in high yield and purity. Moreover, the conditions used to cleave the linker were extended to the release of a base-sensitive DNA-oligonucleotide with 4-N-acetylcytosine residues; the acetyl groups were maintained.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

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