Alvie L. Davis

The syntheses and biological activities of o-aminophenylalanine and related compounds.

Abstract o -Nitrophenylalanine was prepared by the acid hydrolysis of the condensation product resulting from the interaction of o -nitrobenzyl chloride with ethyl acetamidomalonate in the presence of sodium ethylate and subsequently hydrogenated to yield o -aminophenylalanine. Catalytic hydrogenation of ethyl 2-acetamido-2-( o -nitrobenzyl)malonate, followed by acid hydrolysis, yielded 3-aminohydrocarbostyril instead of o -aminophenylalanine. The latter compound in acidic medium readily cyclizes to form 3-aminohydrocarbostyril. Growth inhibition of Escherichia coli 9723 by o -aminophenylalanine is reversed in a competitive manner by phenylalanine over a 100-fold range of increasing concentrations with an inhibition index of 300–1000, whereas the toxicity of 3-aminohydrocarbostyril is not reversed by phenylalanine in a competitive manner.

2,6-Diamino-4-hexynoic acid, a lysine analog

The reaction of 1,4-dichloro-2-butyne with potassium phthalimide yielded N -(4-chloro-2-butynyl)phthalimide, which was subsequently condensed with ethyl acetamidomalonate. Acid hydrolysis of the condensation product gave 2,6-diamino-4-hexynoic acid. Growth inhibition of Leuconostoc dextranicum 8086 by 2,6-diamino-4-hexynoic acid is reversed in a competitive manner by lysine over a hundredfold range of increasing concentrations with an inhibition index of about 10.