Cyclic gamma-Amino Acids and Peptoid Foldamers

Isonipecotic acid provides a stable scaffold with the potential for useful functionalization. Changing the side chains at the β- or γ-positions in the piperidyl ring will tune a peptide towards its biological target or catalytic function. Modifications at these positions is expected to have little effect on the chair conformation adopted by the piperidyl ring. Due to this, substituents will be anchored and may even stabilize the chair conformation and helical structure of the oligomer or peptide. Functionalization is not limited to biological or catalytic applications, as isonipecotic acid has also proven difficult to freeze once dissolved in water. Minor changes to the structure may enhance the antifreeze capability of this peptide, which provides an alternate material for foods that contain antifreeze reagants, such as ice cream. The utility of isonipecotic acid continues to expand as we further explore its structure-dynamic relationship. Further modification is expected to drastically increase the usefullness of isonipecotic acid in the science, material, and engineering field.

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Grant Brewer
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Virginia Tech Intellectual Properties, Inc.
(540) 443-9218
Jatinder Josan
Robert Grams