beta-Hydroxy-alpha-amino acids comprise an important class of molecules with broad application in organic synthesis, medicinal chemistry, chemical biology, and biochemistry. Traditionally, these molecules are prepared using lengthy synthetic sequences that often rely on numerous protecting groups and provide products with reduced stereoselectivities. This presentation will describe our efforts to prepare beta-hydroxy-alpha-amino acids under biocatalytic conditions using a trans-aldolase enzyme. Under the presented conditions, we were able to prepare several amino acid products by reacting threonine with an aldehyde. The reaction could be conducted using purified enzyme or whole cells, and we were able to prepare an amino acid with interesting photophysical properties.

Synthesis of beta-hydroxy-alpha-amino acids under biocatalytic conditions via a transaldolase enzyme

ACS Spring 2022

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