The synthesis of a-(chlorofluoromethyl) -0rnithine 7, -metatyrosine 8 and -glutamic acid 14 is described. Separation of diastereoisomers and relative configuration assignment by X-ray analysis are reported. Assignment of absolute configuration of the four enantiomers of a-(chlorofluoromethyl)ornithine 7 is also described. The inhibitory properties against ornithine decarboxylase, aromatic amino acid decarboxylase and glutamate decarboxylase are reported in terms of diastereoselectivity (8 and 1 4 ) or enantioselectivity (7).* Available from Fluorochem. Ltd., Peakdale Road, Glossop, Derbyshire, SK13 9XE, England. Freon 21 was condensed at -20 "C in a graduated cylinder.
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