Technologies
PDF


WARF: P02304US

Chemical Synthesis of Reagents for Peptide Coupling


INVENTORS -

Ronald Raines, Laura Kiessling, Bradley Nilsson, Matthew Soellner, Yi He, Ronald Hinklin

The Wisconsin Alumni Research Foundation (WARF) is seeking commercial partners interested in developing improved methods for synthesizing phosphinothiol reagents.
OVERVIEWThe Staudinger ligation method for synthesizing peptides requires phosphinothiol reagents that are not commercially available. The current method for making phosphinothiols is complicated (involving four steps) and time-consuming, uses dangerous chemicals, may result in tar-like products, is difficult to effect on a large scale and produces an overall yield of only 39 percent.
THE INVENTIONUW-Madison researchers have developed improved methods for synthesizing phosphinothiol reagents. These synthesis techniques take advantage of phosphorus’s strong interaction with boron, and are based on an easily prepared alkylating agent and a commercially available borane-organophosphine complex. In the methods, the alkylating agent is reacted with the borane-organophosphine complex. Disrupting the resulting phosphine-borane complex and removing the protecting group generates the phosphinothiol reagents.
APPLICATIONS
  • Phosphinothiol production
KEY BENEFITS
  • Requires one less step than the current method
  • Provides an overall yield of 74 percent
  • Can be used to create a limitless variety of phosphinothiols
  • Intermediary phosphine-borane complex is stable to air and moisture, allowing storage at room temperature for several months.
ADDITIONAL INFORMATION
For More Information About the Inventors
Contact Information
For current licensing status, please contact Jennifer Gottwald at jennifer@warf.org or 608-960-9854.
The WARF Advantage

Since its founding in 1925 as the patenting and licensing organization for the University of Wisconsin-Madison, WARF has been working with business and industry to transform university research into products that benefit society. WARF intellectual property managers and licensing staff members are leaders in the field of university-based technology transfer. They are familiar with the intricacies of patenting, have worked with researchers in relevant disciplines, understand industries and markets, and have negotiated innovative licensing strategies to meet the individual needs of business clients.