An improved process for the release of synthetic DNA sequences from a solid-phase capture support. (14th September 2022)

• Record Type: Journal Article
• Authors: Grajkowski, Andrzej; Cawrse, Brian M.; Takahashi, Mayumi; Beaucage, Serge L.
• Is Part Of: Tetrahedron letters. Volume 106(2022)
• Publication Date: 2022-09-14
• Subjects: Sythetic DNA sequences -- Solid-phase synthesis -- Solid-phase purification -- Capture support -- Riboside phosphoramidite -- Ethyl phosphate triester -- Intramolecular cyclodeesterification; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2022.154077
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Abstract: To facilitate the solid-phase purification of synthetic DNA sequences, a riboside phosphoramidite, carrying a 5- O -capture linker and a 2- O -silyl ether protecting group, is incorporated into a DNA sequence during its last solid-phase synthesis cycle. After deprotection and release of the DNA sequence from the synthesis support, the sequence is then covalently linked to a capture support to enable the removal of shorter unbound DNA sequences by simply washing these off the support. The solid-phase purified DNA sequence is then released from the capture support, through an innovative intramolecular cyclodeesterification of its terminal riboside ethyl phosphate triester entity and is isolated in a yield of 94% while displaying an exquisite purity of 97%.