Phosphine-free Stille-Migita chemistry for the mild and orthogonal modification of DNA and RNA

• Verfasst von: Krause, André [VerfasserIn]
• Verfasst von: Muttach, Fabian [VerfasserIn]
• Verfasst von: Jäschke, Andres [VerfasserIn]
• Titel: Phosphine-free Stille-Migita chemistry for the mild and orthogonal modification of DNA and RNA
• Verf.angabe: André Krause, Alexander Hertl, Fabian Muttach, Andres Jäschke
• E-Jahr: 2014
• Jahr: 16 October 2014
• Umfang: 7 S.
• Fussnoten: Gesehen am 23.10.2020
• Titel Quelle: Enthalten in: Chemistry - a European journal
• Ort Quelle: Weinheim : Wiley-VCH, 1995
• Jahr Quelle: 2014
• Band/Heft Quelle: 20(2014), 50, Seite 16613-16619
• ISSN Quelle: 1521-3765
• DOI: doi:10.1002/chem.201404843
• Datenträger: Online-Ressource
• Sprache: eng
• Sach-SW: click chemistry
• Sach-SW: cross-coupling
• Sach-SW: DNA
• Sach-SW: palladium
• Sach-SW: RNA
• K10plus-PPN: 1736473352

Abstract

An optimized catalyst system of [Pd2(dba)3] and AsPh3 efficiently catalyzes the Stille reaction between a diverse set of functionalized stannanes and halogenated mono-, di- and oligonucleotides. The methodology allows for the facile conjugation of short and long nucleic acid molecules with moieties that are not compatible with conventional chemical or enzymatic synthesis, among them acid-, base-, or fluoride-labile protecting groups, fluorogenic and synthetically challenging moieties with good to near-quantitative yields. Notably, even azides can be directly introduced into oligonucleotides and (deoxy)nucleoside triphosphates, thereby giving direct access to “clickable” nucleic acids.