Y. Shimohigashi, Sannamu Lee, N. Izumiya
Nov 1, 1976
Citations
0
Influential Citations
39
Citations
Journal
Bulletin of the Chemical Society of Japan
Abstract
The L-forms of 2-amino-5-(p-methoxyphenyl)pentanoic acid (Amp), 2-amino-5-phenylpentanoic acid (App), and 2-amino-5-(p-hydroxyphenyl)pentanoic acid (Ahp) are constituent amino acids in AM-toxins. The O-methyl linkage of L-Amp was hydrolyzed gradually by heating with hydrochloric acid. A procedure without drastic acid treatment is given for the synthesis and resolution of Amp. Diethyl [3-(p-methoxyphenyl)propyl]acetamidomalonate (3a) was saponified to the corresponding malonic acid (5a), and 5a was converted into acetyl-L-Amp (L-6a) by decarboxylation. The DL-6a and acetyl-DL-App were resolved by acylase to afford L-Amp and L-App, respectively. The L-Ahp was prepared from L-Amp by acid treatment.