Technologies
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WARF: P07405US

Efficient Method of Synthesizing Gamma2-Amino Acids for Applications in Medicine, Materials, Healthcare


INVENTORS -

Samuel Gellman, Yonggui Chi, Li Guo

The Wisconsin Alumni Research Foundation (WARF) is seeking commercial partners interested in developing a highly efficient, three-step method of synthesizing γ2-amino acids.
OVERVIEWUnnatural polymers that contain β- and γ-amino acids are known as "foldamers." These foldamers form long-lasting, predictable structures that are very stable and resistant to proteolytic degradation.  They can be designed to interact with specific targets and have applications in medicine, materials and general healthcare. 

γ2-amino acids are an important type of non-natural amino acid, but they are difficult to make.  Current methods are very inefficient and not useful for scalable synthesis or the synthesis of structurally diverse products.
THE INVENTIONUW-Madison researchers have developed novel compounds and methods for synthesizing γ2-amino acids and related products.  The highly efficient and enantioselective methods are based on Michael reactions of aldehydes with highly reactive nitroethylene.  The reactions are catalyzed by small amounts of readily prepared chiral pyrrolidines in the presence of commercially available and inexpensive carboxylic acids as cocatalysts.  The Michael products, α-substituted-γ-nitrobutyl aldehydes, are valuable building blocks for organic synthesis and can be converted to γ2-amino acids and their derivatives. 
APPLICATIONS
  • Development of pharmaceutically relevant molecules, including antibiotics, hormone mimetics, fat absorption inhibitors and others
  • Development of new materials for information storage and catalysis
  • Beauty products
  • Basic research on foldamers
KEY BENEFITS
  • Enantiomerically pure γ2-amino acids can be made from readily available and inexpensive starting materials.
  • May reduce the cost of manufacturing γ-peptide products
  • Steps may be combined to develop a one-pot method for preparing γ2-amino acids.
  • High overall yields
  • Minimum use of chromatography for purification
  • Amenable to large scale synthesis
  • Mild conditions allow diverse functional groups.
  • Provides—for the first time—a catalytic method for efficient γ2-amino acid synthesis
  • Capable of producing multiple types of chiral organic compounds
ADDITIONAL INFORMATION
For More Information About the Inventors
Publications
  • Chi Y., Guo L., Kopf N.A. and Gellman S.H. 2008. Enantioselective Organocatalytic Michael Addition of Aldehydes to Nitroethylene: Efficient Access to Gamma2-Amino Acids. J. Am. Chem. Soc. 130, 5508-5509.
Contact Information
For current licensing status, please contact Rafael Diaz at rdiaz@warf.org or 608-960-9847.
FIGURES

An efficient three step process for synthesizing gamma<sup>2</sup>-amino acids. An efficient three step process for synthesizing gamma2-amino acids.


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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.