Enantioselective Synthesis of Amino Acids

Period of Performance: 06/01/1997 - 04/30/1998


Phase 1 SBIR

Recipient Firm

TDA Research, Inc.
12345 W. 52nd Ave. Array
Wheat Ridge, CO 80033
Principal Investigator


Amino acid are the main components of proteins and are important elementary nutrients for living organisms. They are also valuable synthetic intermediates for the preparation of a large array of biologically active compounds important to the pharmaceutical industry. Examples of drugs based on amino acids are L-DOPA, L-tryptophan, and beta-lactam antibiotics. Unfortunately, typical production methods for amino acids require expensive and time-consuming optical resolutions to obtain optically pure products. A more desirable way to prepare amino acids would be to enantioselectively hydrogenate carbon-nitrogen double bond (C=N) groups of amino acid precursors. This direct synthesis route could lower costs because only the desired product is formed avoiding the expense of a chiral separation. Unfortunately, the current catalysts generally are not sufficiently active or selective enough to be industrially useful. The objective of this proposal is to prepare optically pure amino acids by enantioselective hydrogenation of compounds with C=N bonds and to show that a variety of amino acids can be economically produced on an industrial scale. PROPOSED COMMMERCIAL APPLICATION This research will lead to the development general method for the production of optically pure amino acids by the enantioselective hydrogenation of compounds with C=N bonds. This will allow the economical production of valuable amino acids for use as pharmaceuticals and synthetic intermediates.