Studies of 1-Amino-2,2-difluorocyclopropane-1-carboxylic Acid: Mechanism of Decomposition and Inhibition of 1-Aminocyclopropane-1-carboxylic Acid Deaminase

Org Lett. 2015 Jul 2;17(13):3342-5. doi: 10.1021/acs.orglett.5b01570. Epub 2015 Jun 23.

Abstract

1-Amino-2,2-difluorocyclopropane-1-carboxylic acid (DFACC) is of interest in the study of 1-aminocyclopropane-1-carboxylic acid (ACC) deaminase due to the increased reactivity of its cyclopropyl functionality. It is shown that DFACC is unstable under near-physiological conditions where it primarily decomposes via specific-base catalysis to 3-fluoro-2-oxobut-3-enoic acid with a rate constant of 0.18 ± 0.01 min(-1). Upon incubation with ACC deaminase, DFACC is found to be a slow-dissociating inhibitor of ACC deaminase with submicromolar affinity.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acids, Cyclic / chemistry*
  • Carbon-Carbon Lyases / antagonists & inhibitors*
  • Carboxylic Acids / chemistry
  • Catalysis
  • Molecular Structure

Substances

  • 1-amino-2,2-difluorocyclopropane-1-carboxylic acid
  • Amino Acids, Cyclic
  • Carboxylic Acids
  • 1-aminocyclopropane-1-carboxylic acid
  • 1-aminocyclopropane-1-carboxylate deaminase
  • Carbon-Carbon Lyases