The synthesis of enantiomers of hex-5-yne-1,4-diamine, a potent irreversible inhibitor of (S)-ornithine decarboxylase (ODC, E,C. 4.1.1.17), is described; the stereospecificity of the inhibition by the (R)-isomer is consistent with a mechanism based on the microscope reversibility principle of enzyme catalysis.
P. Casara, C. Danzin, B. W. Metcalf and M. J. Jung, J. Chem. Soc., Chem. Commun., 1982, 1190 DOI: 10.1039/C39820001190
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