4-oxoheptanedioic acid linker in the synthesis of base-sensitive oligonucleotides



: Leisvuori A, Poijarvi-Virta P, Virta P, Lonnberg H

: 2008

Collection Symposium Series

CHEMISTRY OF NUCLEIC ACID COMPONENTS

: COLL SYMPOS SERIES

: 10

: 401

: 403

: 3

: 978-80-86241-29-6


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.



Last updated on 2025-14-10 at 10:11