University of Delaware OEIP
University of Delaware

Trans-cycloheptenes and hetero-trans-cycloheptenes for biorthogonal labeling

Technology #ud15-35

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Researchers
Dr. Joseph Fox
Research in the Fox group centers on the development of new types of chemical reactions, the application of these new reactions to the synthesis of naturally occurring and designed molecules with biological function, and in the use of design concepts in organic synthesis for applications in biology and materials science.
External Link (www1.udel.edu)
Han Zhang
Yinshi Fang
Managed By
Yops Brad
Director, Technology Transfer Center 3028310147
Patent Protection

Trans-cycloheptenes and hetero-trans-cycloheptenes for bioorthogonal coupling

US Patent Pending WO 2016164565 A1

Technology Description:

The inventive concept here is a process for the use of the 7-membered ring trans-cycloheptene and Si trans-cycloheptenes in biorthogonal chemistry. It provides the fastest known method for biorthogonal labeling. The chemistry of trans-cycloheptene, relative to its homologs, is less explored.  This compound is known to undergo rapid isomerization at room temperature. The inclusion of metal compounds like silicon into the cyclic backbone imparts great stability to these trans-cycloalkenes. Although there are several methods for the production of these compounds, their derivatives are known to be thermally sensitive and moisture sensitive. The invention here describes a novel process for the use of trans-cycloheptenes and Si-trans-cycloheptenes with tetrazines and their ability to undergo stable biorthogonal coupling reactions. The rate constants of these biorthogonal coupling reactions can exceed 107 M-1s-1, thus making sila trans-cycloheptene, the most reactive dienophile reported to date for biorthogonal applications.

Benefits:

  • This is the first process describing the use of the 7-membered ring trans-cycloheptene and Si trans- cycloheptenes in biorthogonal chemistry. 
  • This process represents the fastest rate constants to date for biorthogonal labeling.

Uses/Users:

This process has applications in several areas of medicinal value like,

  • nuclear medicine 
  • cell imaging kits 
  • biomaterials