Article

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

European Journal of Organic Chemistry (impact factor: 3.33). 03/2009; pp.2190-2194

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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Keywords

2′-O-PivOM groups
 
4-N-acetylcytosine residues
 
base-sensitive 2′-O-pivaloyloxymethyl functionalized
 
base-sensitive DNA-oligonucleotide
 
biolabile oligoribonucleotides
 
Chimeric oligouridylates
 
cleave
 
conditions
 
fluoride ion conditions
 
Germany
 
original fluoride ion treatment
 
release oligonucleotides bearing base-sensitive modifications
 
silyl-type linker
 
solid
 
solid support