Trans-cyclooctene amino and hydroxy acids and their use in multiple cycloaddition reactions for labeling of molecules

US10519101B2 · kind B2 · utility

Assignee

• European Molecular Biology Laboratory · DE

Inventors

• Edward Lemke · Mannheim, DE
• Carsten Schultz · Heidelberg, DE
• Tilman Plass · Heidelberg, DE
• Ivana Nikic · Tübingen, DE
• Jan-Erik Hoffmann · Heidelberg, DE
• Iker Valle Aramburu · Heidelberg, DE

Key dates

• Filing date: Jan 14, 2015
• Grant date: Dec 31, 2019
• Expiry date: Apr 1, 2035

Classification

• Technology area (CPC G): Physics
• CPC primary: G01N33/582
• WIPO field: Measurement
• WIPO sector: Instruments

Abstract

The present invention relates to compounds of formula: and methods for linking tetrazines with dienophiles to establish at least two linkages by sequentially performing at least two cycloaddition reactions. The methods in particular allow establishing multi-labeling strategies. In particular, the invention relates to methods for forming linkages by cycloaddition reactions, wherein the method comprises reacting a first alkyl-substituted tetrazine with a first dienophile comprising a trans-cyclooctenyl group followed by reacting a second tetrazine with a second dienophile comprising a cyclooctynyl group, wherein the reaction of the first tetrazine with the first dienophile proceeds in the presence of the second dienophile.