Synfacts 2006(2): 0167-0167  
DOI: 10.1055/s-2005-924806
Bioorganic Chemistry and Organocatalysis
© Georg Thieme Verlag Stuttgart · New York

Hydrogenation Using Chemogenetically Optimized Chemzymes

Contributor(s): Benjamin List, Sebastian Hoffmann
G. Klein, N. Humbert, J. Gradinaru, A. Ivanova, F. Gilardoni, U. E. Rusbandi, T. R. Ward*
University of Neuchâtel, Switzerland
Further Information

Publication History

Publication Date:
23 January 2006 (online)

Significance

This paper describes the chemogenetical optimization of artificial hydrogenases in the reduction of α-acetamidocinnamic acid and α-acetamidoacrylic acid. The metalloenzymes were prepared according to the biotin-avidin technology, 20 streptavidin isoforms obtained by saturation mutagenesis at position 112 were combined with 18 biotinylated ligands. Both α-acetamidodehydroamino acids were reduced simultaneously to investigate the substrate specificity. In general the protein-ligand combinations yield the reduced α-acetamidocinnamic acid in higher enantioselectivities and lower yields. The reaction provides the reduced olefins in up to 94% ee (360 artificial metalloenzymes have been investigated).