Our D-Amino Acid Technology

There is much interest in developing efficient methods for making nonnatural amino acids as they are building blocks for making a variety of blockbuster drugs including plavix, cialis, enalapril and penicillin.

In addition, nonnatural amino acid based peptides are becoming increasingly important as therapeutic agents. We have developed highly efficient ways for making nonnatural amino acids including D-amino acids based on our studies on stereoselective recognition of amino acids at McGIll University and University of Toronto. Our receptors that bind amino acids stereoselectively include organic compounds 1 and 2 (1,2) as well as metal complexes 3 and 4 (3,4). More recently, we used our chiral diamine technology (5,6) to develop efficient methods for making nonnatural amino acids.This latter method is more stereoselective and cost effective than 1 referred to as the ARCA technology (1,7) that we developed earlier.

References

(1)          Park, H.; Kim, K. M.; Lee, A.; Ham, S.; Nam, W.; Chin, J. Journal of the American Chemical Society 2007, 129, 1518.

(2)          Kim, H.; So, S. M.; Yen, C. P.-H.; Vinhato, E.; Lough, A. J.; Hong, J.-I.; Kim, H.-J.; Chin, J. Angewandte Chemie, International Edition 2008,47, 8657.

(3)          Chin, J.; Lee, S. S.; Lee, K. J.; Park, S.; Kim, D. H. Nature (London) 1999, 401, 254.

(4)          Chin, J.; Chong, Y. S.; Bobb, R.; Studnicki, L.; Hong, J.-I. Chemical Communications (Cambridge, United Kingdom) 2007, 120.

(5)          So, S. M.; Mui, L.; Kim, H.; Chin, J. Accounts of Chemical Research 2012, 45, 1345.

(6)          So, S. M.; Kim, H.; Mui, L.; Chin, J. European Journal of Organic Chemistry 2012, 2012, 229.

(7)          Chin, G.; Yeston, J. Science (Washington, DC, United States) 2007, 315, 438.