Mimics of Transaminase Enzymes

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

Research output: Contribution to journalArticle

Abstract

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
Volume108
Issue number8
DOIs
StatePublished - Jan 1 1986

Fingerprint

Pyridoxamine
Transaminases
Stereoselectivity
Enzymes
enzyme
Keto Acids
Acids
Amino acids
acid
amino acid
substrate
Cyclodextrins
Substrates
Amino Acids

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Breslow, R., Czarnik, A. W., Lauer, M., Leppkes, R., Winkler, J., & Zimmerman, S. C. (1986). Mimics of Transaminase Enzymes. Journal of the American Chemical Society, 108(8), 1969-1979. https://doi.org/10.1021/ja00268a040

Mimics of Transaminase Enzymes. / Breslow, R.; Czarnik, A. W.; Lauer, M.; Leppkes, R.; Winkler, J.; Zimmerman, Steven C.

In: Journal of the American Chemical Society, Vol. 108, No. 8, 01.01.1986, p. 1969-1979.

Research output: Contribution to journalArticle

Breslow, R, Czarnik, AW, Lauer, M, Leppkes, R, Winkler, J & Zimmerman, SC 1986, 'Mimics of Transaminase Enzymes', Journal of the American Chemical Society, vol. 108, no. 8, pp. 1969-1979. https://doi.org/10.1021/ja00268a040
Breslow R, Czarnik AW, Lauer M, Leppkes R, Winkler J, Zimmerman SC. Mimics of Transaminase Enzymes. Journal of the American Chemical Society. 1986 Jan 1;108(8):1969-1979. https://doi.org/10.1021/ja00268a040
Breslow, R. ; Czarnik, A. W. ; Lauer, M. ; Leppkes, R. ; Winkler, J. ; Zimmerman, Steven C. / Mimics of Transaminase Enzymes. In: Journal of the American Chemical Society. 1986 ; Vol. 108, No. 8. pp. 1969-1979.
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