B1 Non-refereed article in a scientific journal
4-oxoheptanedioic acid linker in the synthesis of base-sensitive oligonucleotides
Authors: Leisvuori A, Poijarvi-Virta P, Virta P, Lonnberg H
Publication year: 2008
Journal: Collection Symposium Series
Journal name in source: CHEMISTRY OF NUCLEIC ACID COMPONENTS
Journal acronym: COLL SYMPOS SERIES
Volume: 10
First page : 401
Last page: 403
Number of pages: 3
ISBN: 978-80-86241-29-6
Abstract
1,6-dioxaspiro[4,4]nonane-2,7-dione has been found to react readily with 3'-hydroxyl group of nucleosides in the presence of 1,8-diazabisyclo-[5.4.0]undec-7-ene (DBU). The resulted 4-oxoheptanedioic acid tether bears a free carboxy group, which may be used for anchoring the construct to aminoalkylated resins and a 4-oxobutanoate moiety, which allows release of the assembled oligonucleotide by a mild hydratzinium acetate treatment. To demonstrate the applicability of this simple difunctional linker arm, base-sensitive oligonucleotides bearing a biodegradable phosphate protection have been synthesized.
1,6-dioxaspiro[4,4]nonane-2,7-dione has been found to react readily with 3'-hydroxyl group of nucleosides in the presence of 1,8-diazabisyclo-[5.4.0]undec-7-ene (DBU). The resulted 4-oxoheptanedioic acid tether bears a free carboxy group, which may be used for anchoring the construct to aminoalkylated resins and a 4-oxobutanoate moiety, which allows release of the assembled oligonucleotide by a mild hydratzinium acetate treatment. To demonstrate the applicability of this simple difunctional linker arm, base-sensitive oligonucleotides bearing a biodegradable phosphate protection have been synthesized.
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