Directed synthesis of oligophosphoramidate stereoisomers

US8853132B2 · kind B2 · utility

Assignee

• Roche Diagnostics Operations, Inc. · US

Inventors

• Dieter Heindl · Munich, DE
• Dirk Kessler · Peiting, DE
• Angelika Roesler · Sindelsdorf, DE
• Christoph Seidel · Weilheim, DE
• Wilma Thuer · Munich, DE

Key dates

• Filing date: Sep 13, 2013
• Grant date: Oct 7, 2014
• Expiry date: Sep 13, 2033

Classification

• Technology area (CPC Y): Emerging Cross-Sectional Technologies
• CPC primary: Y02P20/55
• WIPO field: Measurement
• WIPO sector: Instruments

Abstract

The trivalent phosphorous atom of a compound is reacted with a reagent in such a manner that a stable phosphate mimetic or a specifier is formed. Phosphoramidites with a phosphorous atom containing at least one hydroxyl residue which is provided with a protective group are reacted for this purpose with a free hydroxyl group: In the first synthesis cycle the hydroxyl group is linked to a solid support via a cleavable or non-cleavable linker. In further synthesis cycles the hydroxyl group is created by cleavage of the protective group from the growing oligomer. This results in formation of a phosphorous acid triester which is reacted with azides. By selecting suitable monomers for the synthesis which have a defined stereoconformation compounds of Formula 1 are produced in a stereocontrolled manner.