4-Oxoheptanedioic acid: an orthogonal linker for solid-phase synthesis of base-sensitive oligonucleotides

Nucleotides and Nucleic Acids; Oligo- and Polynucleotides

“…Oligonucleotides are removed from support using 0.2 M Et 3 N d HF at room temperature in 4 h. 5 4-Oxoheptanedioic acid has also been used as a linker between CPG and the first nucleoside, which is removed by treatment with hydrazinium acetate allowing for orthogonal chemistry involving removal of other base protecting groups on solid support. 6 The modified CPG (3) has been used for the synthesis of oligonucleotides as a support that can be removed under mild aqueous conditions (PBS, 90 1C, 2 h). 7 A two-step approach for the synthesis of phosphorothioate oligonucleotides in solution has been reported that uses first phenylacetyldisulfide (PADS) followed by 3H-1,2-benzodithiol-3-one.…”

“…40 Cyclic oligonucleotides have also been prepared by Click chemistry using an N 3 -propargyl-dT and N 3 -azidoethyl-dT at the termini of the oligonucleotides. 41 The masked phosphate (6) has been incorporated into DNA to study the role of telomeric RNA in telomerase activity. 42 Photoirradiation of (6) generates a nitrene that can be used for trapping of proximal RNA of the telomerase region by crosslinking to it.…”

Combinatorial Chemistry Online

“…Nucleosides have been derivatised with this simple difunctional linker arm, anchored to a solid phase and subjected to synthesis and subsequent release of oligonucleotides bearing base-sensitive biodegradable phosphate protection. 11 Peptides are limited in their use as drugs due to low cell permeability and vulnerability to proteases. In contrast, peptoids are immune to enzymatic degradation and some peptoids have been shown to be relatively cell permeable.…”

Dim and Dmoc Protecting Groups for Oligodeoxynucleotide Synthesis

“…They can co-exist with the functional groups of ODNs but cannot survive the harsh deprotection and cleavage conditions used in typical ODN synthesis technologies. Many efforts have been made to solve the problem (Avino & Eritja, 1994;Hayakawa, Wakabayashi, Kato, & Noyori, 1990;Leisvuori, Poijarvi-Virta, Virta, & Lonnberg, 2008;Matray & Greenberg, 1994;Ohkubo, Ezawa, Seio, & Sekine, 2004;Virta, 2009) but an ideal technology involving synchronized strategies for exo-amine and phosphate protection, and ODN linking to solid support to enable mild conditions for ODN deprotection and cleavage has not appeared.…”