Mimics of Transaminase Enzymes

R. Breslow, A. W. Czarnik, M. Lauer, R. Leppkes, J. Winkler, S. Zimmerman

Research output: Contribution to journalArticlepeer-review


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 also observed. A tetrahydroquinoline system related to pyridoxamine was synthesized to permit the stereochemically defined placement of a basic catalytic group. This converted keto acids to amino acids with good stereoselectivity for the formation of optically active products.

Original languageEnglish (US)
Pages (from-to)1969-1979
Number of pages11
JournalJournal of the American Chemical Society
Issue number8
StatePublished - 1986

ASJC Scopus subject areas

  • Catalysis
  • General Chemistry
  • Biochemistry
  • Colloid and Surface Chemistry


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