Mimics of Transaminase Enzymes

Article abstract of DOI:10.1021/ja00268a040

Pyridoxamine has been attached to the primary side and to the secondary side of β-cyclodextrin; the resulting compounds convert α-keto acids to amino acids with substrate selectivity and some stereoselectivity.Pyridoxamine has also been attached to a synthetic macrocycle; the attached binding group showed substrate selectivity.Chains carrying catalytic basic groups have been attached to pyridoxamine; appropriate systems catalyze the prototropic rearrangement characteristic of transamination.A catalyzed HCl elimination involving chloropyruvic acid was observed.A tetrahydroquinoline system related to pyridoxamine was synthesized to permit the stereochemically defined placement of a basis catalytic group.This converted keto acids to amino acids with good stereoselectivity for the formation of optically active products.